Fresh horses have an edge in the 2019 Belmont Stakes

by Noel Michaels

Notwithstanding the victory in 2018 of Triple Crown winner Justify, the Belmont Stakes (G1) is truly one of the great unheralded graveyards for favorites in all of horse racing. It has become increasingly difficult for a horse who has already won, or even competed, in both of the first two legs of the Triple Crown to win the Belmont Stakes. Because of this, no matter how good the favorite might look in the Belmont Stakes, it is still worthwhile to bet against them.

Part of the reason favorites do badly in the Belmont Stakes is because they are usually already depleted after having run in the Kentucky Derby (G1) and Preakness (G1), and are facing off against fresher horses. Additionally, the Preakness, in particular, seems to have become a negative key race in terms of running successfully in the Belmont Stakes.

Dating back to Commendable in 2000, 10 of the last 19 Belmont Stakes winners had not run a race in the five weeks between the Kentucky Derby and Belmont. When you narrow it to four weeks out from the Belmont to accommodate horses exiting the local prep race in the Peter Pan (G2), then 12 of the 19 Belmont winners had at least a four-week layoff going into the race.

Belmont winners Tapwrit, Creator, Palace Malice, Union Rags, Summer Bird, Jazil, Birdstone, Empire Maker and Commendable had all run in the Kentucky Derby but skipped the Preakness in favor of other methods of readying for the Belmont Stakes. Filly Rags to Riches had no race between the Kentucky Oaks (G1) and the Belmont.

Tonalist and Drosselmeyer , the 2014 and 2010 Belmont winners, skipped both the the Kentucky Derby or Preakness but did have a race in the Peter Pan and Dwyer Stakes (G2), respectively. They won the Belmont off four-week layoffs. Before that Lemon Drop Kid was a troubled also-ran in the Derby who also competed in the Peter Pan, which has proven to be an effective Belmont Stakes prep in recent history and is a good place to look for a longshot.

Belmont Stakes winners of yore usually were war horses who danced every dance in the Triple Crown series, but that’s no longer the trend to look for in a Belmont winner. A quintet of recent Belmont winners – Tonalist (2014), Drosselmeyer (2010), Da’ Tara (2008), Rags to Riches (2007) and Sarava (2002) – were making their Triple Crown debuts in the third jewel. The new shooters in this season’s Triple Crown races who are entered in the Belmont Stakes are Joevia, Sir Winston and Intrepid Heart.

This year, only Preakness winner War of Will will have raced in all three Triple Crown races. That has to be considered a negative in terms of his chances to win. Also, Everfast and Bourbon War are exiting the Preakness three weeks ago, which is a possible knock against those contenders.

Finally, the group of Belmont Stakes-bound horses who ran in the Kentucky Derby and then skipped the Preakness, giving them the experience of running in the Derby and also the benefit of five weeks off between races, are Master Fencer, Tax, Spinoff and Tacitus. This year’s advantage could go to these horses, not only to win but also in the exactas and trifectas if you are betting the exotics.

Since Tacitus is the morning-line favorite in this year’s Belmont, you can choose a longshot win bet amongst Tax (15-1), Spinoff (15-1) or Master Fencer (8-1).

Best of luck!

PHOTO: Master Fencer (c) O’Leary

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Maven aims to become American Pharoah’s first stakes winner in Tremont

The Wesley Ward-trained and bred Maven became the first North American winner at stud for Triple Crown winner American Pharoah when he led throughout at Aqueduct on April 19. Now, the chestnut colt will try to become the first stakes winner by his sire when leading a field of nine postward in Friday’s $150,000 Tremont S. at Belmont Park.

Bred in the Bluegrass State, the May foal was heavily backed in his debut and he delivered with a sharp tally under today’s pilot Dylan Davis. The colt broke well and was a bit headstrong, until given his cue at the top of the lane at Aqueduct. He responded like a good one when being challenged by next-out graduate Lebda, finishing a half-length clear under the line.

Maven shows four perfectly spaced half-mile works leading up to his stakes bow on Friday. Those morning breezes all came on the green, where Maven could eventually be destined for. The colt is a son of three-time stakes winner Richies Party Girl, who was a one-turn specialist on the turf who registered a victory in the 2013 Juvenile Turf Sprint on Breeders’ Cup Saturday.

The Tremont field attracted some other nice prospects, too. Rookie Salsa is perfect from two starts to date, which includes a 27-1 upset in the Kentucky Juvenile S. for conditioner Jeremiah O’Dwyer. The Two Step Salsa colt won at first asking at Laurel Park prior to his stakes surprise.

Fore Left went off at 6-5 odds in his first start at Santa Anita and led at every call for trainer Doug O’Neill. The son of Twirling Candy makes the cross-country trek for the Tremont, as does jockey Mario Gutierrez.

Ward’s Dixie Mo gives this outfit a pair of players in the field. The daughter of Uncle Mo, who dominated in an off-the-turf sprint at Indiana Grand first time out, will tackle the boys in this heat.

The Steve Asmussen-trained Memorable defeated six foes at Churchill Downs on May 2 and he could be any kind going forward. Kentucky-bred colt put in a sharp half-mile move at Keeneland on Sunday to ready for his stakes debut.

American Pharoah will undoubtedly get stakes winners in 2019, and it would be fitting if his first were the horse who represented him with his initial North American victory at stud.

Maven wins his debut at Aqueduct (c) NYRA/Coglianese Photography

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Fluid three-year-old title race a good thing for second half of 2019

We all knew well ahead of time there was not going to be a Kentucky Derby (G1)-Preakness (G1) double pulled off this year, and given the events that transpired earlier this month that’s not a bad thing.

As much as we look forward to the occasional Triple Crown bid and the mainstream attention the sport receives in those circumstances, it’s also not a bad thing for a championship race to extend into the second half of the year. That wasn’t the case in two of the past four seasons, so the major three-year-old races ahead will presumably have added relevance this time around.

So who’s the three-year-old male division leader after the first two legs of the Triple Crown? If the polls closed today, the race would likely be decided between Maximum Security and War of Will.

A nuanced view of the Kentucky Derby outcome is that Maximum Security was indeed the best horse in the race yet was justifiably disqualified due to bad behavior on the second turn. He also has the victory in the Florida Derby (G1) going for him.

War of Will has a trio of graded stakes wins in the Preakness, Risen Star (G2), and Lecomte (G3), and two excusable losses — in the Louisiana Derby (G2), where he injured himself soon after the start, and the Kentucky Derby, where he was the first to bear the brunt of Maximum Security’s misdeeds while arguably short of complete fitness having not had a useful prep in the preceding 11 weeks.

What about Kentucky Derby winner Country House? While officially the winner of the most prestigious event in the division, the rest of his record to date does not stand up to closer scrutiny. He finished second to War of Will in the Risen Star, fourth in the Louisiana Derby, and third in the Arkansas Derby (G1).

The winner of that Arkansas Derby was Omaha Beach, who perhaps would receive a sprinkling of support if the vote were held now. Also the winner of a Rebel (G2) division, there’s probably quite a few (myself included) who feel that, if not for the untimely throat issue that resulted in his scratching from the Kentucky Derby as the morning line favorite, he might have proved better than all of these over a surface he would have relished. Think of the drama that might have potentially been avoided, too.

Of these four, only War of Will is a likely participant in the Belmont Stakes (G1). Another victory there would undoubtedly give him a leg up on divisional honors. It’s not impossible to stop a horse with two classic wins from winning the divisional championship, but it’s been rare in the Eclipse Award era. The last occurrence was 1994, when Holy Bull defeated Tabasco Cat (though some of us sided against Funny Cide and California Chrome in the interim). Before that you have to go back to 1972, when Key to the Mint outpolled Riva Ridge.

(It also happened in 1969, 1968, 1966, 1950, 1944, 1942, 1939, and 1936.)

Maximum Security’s next significant goal is the Haskell Invitational (G1) in July, while Country House and Omaha Beach continue to recover from recent ailments. And don’t sleep on another three-year-old popping up or improving late in the year. Recent champions like West Coast, Arrogate, and Will Take Charge were on no one’s championship radar at this point in the season.

While there are two colts with a slight edge over their competition for the Eclipse Award at this point, the beauty of all this is that the race remains very fluid as we approach the Memorial Day holiday and head into summertime. Not a bad thing at all.


(c) Gustavsson

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Afleet Alex: Against All Odds


A wise person once said, “Sometimes you have to be knocked down lower than you’ve ever been in order to stand taller than you were before.”

We see it in sports, when athletes faced with seemingly insurmountable adversity overcome great obstacles against all odds. There was Reggie Miller scoring eight points in nine seconds to spark his Indiana Pacers’ amazing comeback against the New York Knicks. There were the Cleveland Indians erasing a 12-run deficit against the Seattle Mariners.

And in 2005, there was the miraculous recovery and triumph by Afleet Alex in the Preakness Stakes (G1).

That last one – as are all great sports comebacks – will be remembered for as long as anyone races horses.

His story began in 2002. Shortly after Afleet Alex’s entrance to the great wide world, his mother rejected him, leaving little Alex an orphan. Bottle fed until being placed with a nurse mare, the son of Northern Afleet became accustomed to human interaction and affection in ways most future racehorses do not.

Afleet Alex didn’t hail from racing royalty. He was, instead, purchased as a two-year-old for $75,000, a modest sum compared to other horses in the sale. This was the first racehorse purchased by his ownership group, the Cash Is King Stable formed by Chuck Zacney.

Clearly a remarkable athlete from the get-go, winning his first three starts by a combined 28 1/2 lengths, Afleet Alex continued to outrun his price tag. He won the Sanford (G2) and Hopeful (G1); placed in the Champagne (G1) and Breeders’ Cup Juvenile (G1); and dominated the Arkansas Derby (G1), his final start before the 2005 Kentucky Derby (G1).

Along the way, Zacney and his Cash Is King partners learned of another Alex’s story – the both tragic and inspiring tale of Alex Scott, an eight-year-old girl who had recently lost her battle with cancer, but not before opening a lemonade stand, pledging to earn $1 million for childhood cancer research. Though Alex Scott’s time on Earth had sadly come to an end, her inspiration for lemonade stands everywhere continue to honor her and raise money for her cause.

Cash Is King began donating portions of Afleet Alex’s winnings to Alex’s Lemonade Stand anonymously before taking public the little girl’s story on racing’s grandest stage: the Triple Crown.

Because Afleet Alex was a fan favorite, it was the hope of many in the crowded stands of Churchill Downs that the little horse with the big heart would prevail in the Kentucky Derby. However, he would run out of gas late to finish a narrowly-beaten third.

It would be the last time he would lose a race.

Two weeks later, Afleet Alex entered the Preakness Stakes starting gate the 3-1 favorite, and he would go on to victory in one of the most memorable Middle Jewels in history.

Far back early, Afleet Alex would make up ground throughout the far turn, before launching his bid at the top of Pimlico’s stretch. As he began to accelerate, a weaving Scrappy T, who currently led the field, looked to decimate his chances when he veered outward, directly into the way of Afleet Alex.

Scrappy T with Ramon Dominguez bumps Afleet Alex with Jeremy Rose up in the final turn of the 2005 Preakness Stakes at Pimlico Race Course. (c) Joseph DiOrio/

The next few seconds, before a worldwide audience, passed in what could only be described as slow motion – complete with sinking feelings of desperation.

Afleet Alex dropped to his knees with nowhere to go, as Scrappy T entered his path with no warning. A moment in which all the world stood still, his connections froze – the plucky bay colt’s life flashing before their eyes.

In Thoroughbred racing, when incidents like this occur, races are lost, or horses and jockeys are sometimes injured. But on this day, Alex would not be denied. In one single motion, the horse whose heart would not quit, rose to his feet once more, to launch a furious run for home – his competition left lengths behind.

It was a feat unimaginable, not because Afleet Alex was underestimated, but because recovery was thought to be impossible. It was almost as if little Alex Scott, whose bravery and resilience would outlive her tired frame, reached down from the heavens to pluck up the little colt who ran in her honor, only to set him back down in a blaze of invincibility.

After his astounding Preakness Stakes victory, both Afleet Alex and the Alex he ran for, were front-page news the world over. Three weeks later, on the day he would run in the Belmont Stakes (G1), 30 racetracks would feature lemonade stands in Alex Scott’s honor, earning thousands of dollars more for the foundation she built.

And so it was only fitting, that once more, Afleet Alex stormed home in one sweeping move, to capture the Belmont before 62,000 people in the stands, as well as television audiences around the globe in a way that left fans and hardened racing veterans alike saying, “Man, that horse should have won the Triple Crown.”

But when thinking of Afleet Alex, his coming up just shy of a Triple Crown is not what is remembered most. It is, instead, his message of perseverance – his refusal to be broken, his unwavering will to conquer all – and lastly, his link to a little girl who shared his name, and the legacy she left behind.

Top photo: Afleet Alex wins the 2005 Preakness at Pimlico (c) Michael J. Marten /

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Projected cast for 2019 Preakness: How the Middle Jewel is shaping up

For the first time since 1951, the principals from the Kentucky Derby (G1) are all absent from the Preakness (G1). But if the Middle Jewel doesn’t lend itself so much to a “rematch” story line, Saturday’s classic in Baltimore is giving a few Derby competitors a fresh playing field versus several up-and-comers.

Leading the cast is Improbable, who aims to give Hall of Fame trainer Bob Baffert a record eighth Preakness. The 4-1 post time Derby favorite, he crossed the wire in a fairly even fifth (promoted to fourth via the disqualification of Maximum Security). That was the second straight sloppy track that the big chestnut encountered, following his runner-up effort to Omaha Beach in the Arkansas Derby (G1).

Despite the fact that he was beaten only a length by the early Kentucky Derby favorite at Oaklawn, I didn’t get the sense that Improbable was in love with the slop. To me, he gave off the vibe of one tolerating it and plowing through on class. Then again, the blinker experiment had him all at sea from the beginning of the Arkansas Derby anyway, so I could be misreading or over-interpreting it. In any event, the blinkers-off Improbable did not really pick up in the slop at Churchill as he was beaten a shade over three lengths, and he’s manifestly better than that.

If the advance forecast holds, Improbable stands to get a fast surface at Pimlico, and we could well see him back to his best. The City Zip colt remains capable of the brute power he showed in last fall’s Street Sense and Los Alamitos Futurity (G1).

War of Will would like a word with Maximum Security after the fracas on the Derby far turn, but until he gets that opportunity, the Mark Casse trainee at least deserves a clean trip in the Preakness. While we’ll never know exactly how much the interference cost him, War of Will maintained his contending position for a long way before fading to eighth (elevated to seventh). And the immediate postrace quotes suggested he just got tired. Casse relayed what jockey Tyler Gaffalione had told him: “if he could have gotten him to relax a little he thought he would finish a little better.”

Indeed, War of Will had every right to feel it that last furlong even if he hadn’t been hampered or raced too keenly in the early going. Remember his awkward steps at the beginning of the Louisiana Derby (G2), where he lost his action and never factored in ninth? He got virtually nothing out of his final Kentucky Derby prep, six weeks ahead of the first Saturday in May. So War of Will had not had a proper race since his Risen Star (G2) victory back on…February 16.

Thus War of Will’s pattern of races – but not his overall profile – reminds me of Bravazo last year. Bravazo also won the Risen Star, got nothing out of a bizarre trip in the Louisiana Derby, ran a sneakily-good sixth behind Justify in the Churchill slop, moved forward a light year at Pimlico, and almost upset the Triple Crown winner. War of Will has the same entitlement to improve off the Derby, along with the advantage of being a naturally more brilliant performer than Bravazo.

The other two exiting the Derby are Win Win Win and Bodexpress. Win Win Win, who brought exotics appeal in the wake of a troubled but hard-charging second in the Blue Grass (G2), raced far back early at Churchill and got no closer than 10th (officially placed ninth). The Mike Trombetta pupil is eligible to return to his prior form, but still needs to step up to become a win threat. Bodexpress, part of the collateral damage on the Derby far turn, is still a maiden albeit one with a respectable level of form for Gustavo Delgado. Runner-up to Maximum Security in the Florida Derby (G1) two back, the Bodemeister colt aims to become the first to break his maiden in the Preakness since Refund (1888).


The historical trends strongly favor Derby alumni winning the Preakness, but the 2019 Triple Crown trail hasn’t exactly gone according to script. This is just the type of year for a new shooter to defy the stats.

The most logical place to look is among the “bubble” horses who might have been a tad unlucky not to make the Derby field, and Bourbon War is Exhibit A. Trained by Mark Hennig, the Tapit blueblood brings the rich vein of Florida form that stood up well in the Derby. Bourbon War was a closing second to Code of Honor in the Fountain of Youth (G2) and fourth in the Florida Derby, where he had no chance given the race shape benefitting the front runners. (Saturday’s Peter Pan [G3] is an additional data point, with Fountain of Youth alum Global Campaign prevailing.)

Sometimes my penchant for counterfactuals can lead me astray, but just as a thought experiment, what if Bourbon War had been in the Wood Memorial (G2) instead of the Florida Derby? Isn’t there a reasonable chance he gets more points at Aqueduct than at Gulfstream (all he needed was a third in the Wood)? And gets in the Derby? In that alternate universe, Bourbon War might have brought a stronger resume into Baltimore. At a minimum, the talented colt is adding blinkers for the Preakness and figures to get an honest pace.

The “what-if” game applies to Marylander Alwaysmining in a slightly different way. He’s compiled a six-race winning spree capped by the Federico Tesio – a Preakness “Win and You’re In” – without venturing into Derby scoring races. Yet he’s turned in Brisnet Speed figures in the high 90s of late, implying that he would have been competitive had connections attempted Derby preps. Trainer Kelly Rubley’s patient game might prove wisest in the end, as Alwaysmining enters the biggest test of his life riding a wave of confidence. And he’s not without some collateral form, having beaten Win Win Win in the Heft last December. His defeat of Gray Magician, the future UAE Derby runner-up, in the Miracle Wood is less compelling but still noteworthy. A front runner in the first five races of his current skein, Alwaysmining proved he could stalk and pounce in his 11-length demolition job in the Tesio.

Bubble list veteran Signalman has perhaps the most gnawing what-might-have-been for his connections. Had they entered as an also-eligible, he would have drawn into Derby 145 upon the scratch of Haikal. Signalman had scored his signature win in last fall’s Kentucky Jockey Club (G2) in similarly sloppy conditions at Churchill, following a third in the Breeders’ Cup Juvenile (G1) over the same track. The same points don’t promise to carry over to Pimlico. Moreover, Signalman has yet to perform up to his 2018 form, most recently finishing third in the Blue Grass. He’ll have to move forward markedly third start off the layoff for Ken McPeek.

Owendale has the look of a rapid improver after capturing the Lexington (G3) with a monster circling move. The proverbial light bulb came on one start too late, unfortunately, to make the Derby. The Brad Cox trainee had made no impact in his stakes debut in the Risen Star, winding up eighth behind War of Will and promoted Kentucky Derby winner Country House. Although not as gaudy as the Gulfstream form, the Risen Star has its own graduate success stories, with Plus Que Parfait going on to take the UAE Derby (G2) and Mr. Money garnering the Pat Day Mile (G3). In hindsight, there was no disgrace to being unplaced in the Risen Star, and Owendale’s dynamic breakthrough at Keeneland came at the expense of several Derby trail veterans.

Chief among them is “bubble” horse Anothertwistafate. After dominating the El Camino Real Derby – the first “Win and You’re In” for the Preakness – on his home Tapeta at Golden Gate Fields, Anothertwistafate met with disadvantageous trips in his ensuing Derby points races on dirt. In the Sunland Park Derby (G3), Cutting Humor was already launching his winning move by the time Anothertwistafate could angle out, and his rally fell a neck short. Nevertheless, Cutting Humor had been summarily dismissed by Bourbon War in a Gulfstream allowance, so on a literal reading of form, Anothertwistafate has a gap to close with him.

Anothertwistafate’s gap with Owendale isn’t merely hypothetical, but actual, from his 1 3/4-length defeat in the Lexington. Although Anothertwistafate was temporarily in traffic, he did cut the corner into the stretch once clear, and it would be rash to claim he’d have outfinished Owendale. That said, Anothertwistafate didn’t have an ideal scenario on the turnaround. Marooned at Sunland when he couldn’t return to Golden Gate due to an EHV-1 positive back home, the Blaine Wright trainee actually worked in New Mexico before shipping again to Keeneland. Now Anothertwistafate not only has better spacing between races going into the Preakness, but he’s also been training in the friendly confines of Golden Gate. The son of Scat Daddy (sire of Justify) can put a better foot forward at Pimlico.

Like Anothertwistafate and Alwaysmining, Laughing Fox prevailed in a Preakness “Win and You’re In,” in his case the inaugural Oaklawn Invitational. But unlike them, Laughing Fox also competed in a major Derby prep, the Arkansas Derby, and finished a creditable fourth. Although Omaha Beach and Improbable were in a race of their own that day, Laughing Fox was only a length off the third-placer – Country House.

Trained by Hall of Famer Steve Asmussen, the flashy Union Rags colt had a productive meet in Hot Springs. Laughing Fox won two straight, including a Presidents’ Day allowance in a time comparable to the Southwest (G3) later on the card, before a troubled seventh in the Omaha Beach/Game Winner division of the Rebel (G2). Then he resumed his upward curve, and last out rallied stoutly to beat some useful sorts in the nine-furlong Oaklawn Invitational. The broad parallel is with Owendale, if without quite the same panache.

Oaklawn has produced two more Preakness contenders, both longshots. Warrior’s Charge, a stablemate of Owendale from the Cox barn, came to hand too late for a Triple Crown nomination. So Ten Strike Racing and Madaket Stables must stump up $150,000 to supplement the Munnings colt, who will make an audacious stakes debut off maiden and entry-level allowance romps. Warrior’s Charge promises to contribute to the pace after both wire jobs in solid time.

Hall of Fame trainer and six-time Preakness winner D. Wayne Lukas pitched Market King onto the list Sunday. A distant third in Omaha Beach’s Rebel, he retreated to 11th after a wide trip in the Blue Grass. If you’re trawling for positive talking points, he’s a Niarchos Family-bred blueblood (like War of Will), bred on a similar cross to Owendale (Into Mischief over A.P. Indy), and training forwardly.

Preakness Starting Gate (c) Jim McCue/Maryland Jockey Club

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What to take away from Kentucky Derby contender works with clocker Gary Young

The special Kentucky Derby editions of Turf Talk features exclusive analysis with highly respected clocker Gary Young. Analysts Scott Shapiro and Ed DeRosa discuss with Gary how Kentucky Derby contenders look as they prepare for the First Saturday in May. Find the 2019 episodes all in one place, listed below!

May 1, 2019
Gary shares opinions on his first handicapping looks for the Kentucky Derby field. What do the works tell him about performance from Post Position and Odds applied?

April 30, 2019
Track time for several Kentucky Derby hopefuls.

April 29, 2019
Featuring the works of Long Range Toddy and more!

April 28, 2019
Featuring the works of Kentucky Derby contenders Tacitus, Country House, By My Standards and more!

April 27, 2019
Featuring the work of Kentucky Derby contender Omaha Beach.


TURF TALK video archive playlist

PHOTO: Coady Photography/Churchill Downs

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Jockey Boland

Phenom to Journeyman: The Riding Life of Bill Boland

For almost seven decades, Bill Boland has been able to call himself a winner of the Kentucky Derby. The Hall of Fame jockey recently looked back on his career and his stories are priceless.


The Atomic Age had begun only five years earlier. Two ambitious politicians in their 30s, John F. Kennedy and Richard Nixon, were serving just their second terms in Congress. Lucille Ball was starring in a modestly rated radio sitcom called “My Favorite Husband” and was more than a year away from appearing on a relatively new gadget called television. Screen starlet Elizabeth Taylor, age 18, was about to embark on her first marriage.

This is a narrow glimpse at the way the world looked on May 6, 1950. It also happened to be the first Saturday of that month, meaning it was Kentucky Derby Day. However, for those not actually in Louisville that afternoon, your only chance of learning the outcome in real time was listening to Clem McCarthy’s error-filled race call on CBS Radio.

Bill Boland remembers that day and many others from that spring quite well. Less than a year removed from riding his first winner, the 16-year-old apprentice from Texas reached the pinnacle of American racing in almost record time, guiding King Ranch’s Middleground to victory in the Run for the Roses.

Youth does indeed have its advantages. An incredible 69 years after joining the exclusive fraternity, Boland is the most senior surviving jockey to have won a Kentucky Derby. Now 85 and a longtime retiree, Boland recently shared memories of that Derby, the 1950 Triple Crown series, and other highlights of his Hall of Fame career.


On May 17, 1949, not long after riding his first winner, Boland climbed aboard a first-time starter named Middleground in a 4 1/2-furlong maiden race run down the old, diagonal Widener course at Belmont Park. On the perceived lesser half of the King Ranch entry sent postward as the 6-5 favorite, Middleground nonetheless outran stablemate Beau Max to win by three-quarters of a length while toting a mere 104 pounds.

“He was a nice, docile little horse,” Boland said of Middleground. “He would do anything you asked him to do–easy to gallop in the morning, easy to work. He wasn’t rank or anything, trying to overdo it. Just a nice little horse. He wasn’t too big, but he was put together pretty good.”

It was the only time that season Boland rode the son of Bold Venture. The stable’s primary rider, Dave Gorman, rode Middleground to victory in three of his next four starts, including a six-length tour de force in the Hopeful Stakes at Saratoga. Unfortunately, Middleground was not the soundest colt as the Hopeful proved to be his final start at 2.

“He had osselets,” Boland said. “His ankles were growing, they stopped (training) and they blistered him.”

Middleground’s absence that fall enabled Hill Prince to earn champion juvenile colt honors. However, Middleground was made the 126-pound highweight on the Experimental Free Handicap, two pounds higher than Hill Prince. The debate over which colt was better would rage over the winter months.

Middleground was trained by a fellow Texan, Max Hirsch, a former jockey who had earned respect and acclaim from all quarters of the industry. Prior to becoming stable trainer to Robert J. Kleberg Jr.’s King Ranch, Hirsch had trained future Hall of Fame runner Sarazen and Bold Venture, the 1936 Kentucky Derby and Preakness winner. For Kleberg, Hirsch conditioned 1946 Triple Crown winner Assault, also a son of Bold Venture.

“He was tough, but he was very fair,” said Boland of Hirsch. “He was easy to ride for, as long as you rode to his orders–or tried to. I had no trouble riding for him.”

A young Bill Boland stands behind Middleground in the winner’s circle following their 1950 Kentucky Derby victory (c) Churchill Downs

In that vastly different era, neither Middleground nor Hill Prince ran in an official race at 3 until the start of the New York season at Jamaica in April. But Middleground had gotten in some preparatory work down south.

“I went to California, and Middleground wintered in Columbia, South Carolina,” Boland said. “When Santa Anita was over, I went back to Columbia. They had trials, which was like a charity event every year in Columbia, and I rode him going three-eighths of a mile, and he finished second.”

Circumstances also worked to Boland’s advantage in retaining the mount on Middleground in the lead-up to the Kentucky Derby.

“Dave (Gorman) had a falling out with Max Hirsch, and so that left me to be the rider,” Boland said. “Eddie Arcaro had the mount if he wanted it, but he picked Hill Prince.”

Bypassing the six-furlong Experimental Free Handicap No. 1, in which he would have conceded Hill Prince two pounds, Middleground instead made his season debut six days later, April 11, in a six-furlong allowance. He finished second to Ferd, one of the better sprinters in that crop of 3-year-olds.

On April 17 Middleground raced against older horses in an overnight handicap going 1 1/16 miles. Made the 4-5 favorite despite conceding significant weight on the scale, he finished second to the 5-year-old My Request, whose 14 previous stakes wins included the Wood Memorial, Dwyer and New Orleans Handicap. Middleground did outrun Loser Weeper, the previous year’s Met Mile winner.

Middleground met Hill Prince for the first time in the 1 1/16-mile Wood Memorial on April 22. Next Move, the eventual champion 3-year-old filly, set the pace but carried Middleground wide into the stretch when she began to tire. Hill Prince shot through on the inside to win by two lengths from Middleground.

“He’d only run a few times as a 2-year-old. (Hirsch) was trying to get him experience and trying to get him to peak at the same time,” Boland said. “(Next Move) didn’t cost him in the Wood Memorial.”

Middleground turned in his final prep, his fourth in a span of 22 days, in the Derby Trial at Churchill Downs over a mile May 2. He was beaten two lengths by an unheralded runner named Black George over a very sloppy track.

“Middleground wasn’t the best mud horse in the world. He tried,” Boland said.

No Trouble

The string of second-place finishes perhaps soured the public’s feelings about Middleground for the Derby, as he started as the 7.90-1 fourth choice. Encouragingly, the track had dried out sufficiently from rain earlier in the week and was labeled fast.

Also in Middleground’s favor was Boland’s hot riding. The Saturday before the Kentucky Derby, he won the Gallant Fox Handicap at Jamaica aboard Better Self, and on Derby eve had guided Ari’s Mona to a track-record-setting score in the Kentucky Oaks.

“The day of the Derby, I walked in the paddock and my orders were, ‘I don’t want you within ten lengths of the lead turning down the backside,’ and that was all,” Boland said.

Hirsch had good reason to not want Middleground up close, as a blinding pace was assured, courtesy of Santa Anita Derby winner and 8-5 favorite Your Host. Hill Prince was the second choice at 5-2.

While he might not have followed Hirsch’s orders to a T, as Middleground was only six lengths or so back after a half-mile, the colt was sufficiently positioned as Your Host set a swift opening four furlongs in :46 3/5.

“I went around the first turn, got on the fence turning down the backside and got through half the field,” Boland said. “By the time I got to the three-eighths pole, I was getting ready to go to the lead. Got through on everybody. No trouble.”

It was a clean trip for Middleground and for Hill Prince, whom Arcaro had attempt to rally inside of Middleground in the stretch, but the Texas-bred proved best and won by 1 1/4 lengths. The final time of 2:01 3/5 at the time was the second-fastest Derby, a fifth off Triple Crown winner Whirlaway’s track record.

“The fans were really great about it. They gave me a great applause,” Boland said of the post-race scene. “After the race I was walking back to the barn, and I had the flowers they give you. The crowd was clapping. It was really nice.”

In retrospect the field Middleground defeated in the Derby was really nice, too. In addition to future Hall of Famer Hill Prince, Middleground also defeated Sunglow and Your Host, who respectively sired Sword Dancer and Kelso. And both played notable roles in Boland’s story later in his career.

Middleground’s 1950 Kentucky Derby

Legs and Heart

A week after the Derby, both Middleground and Hill Prince started in the Withers Stakes at Belmont over one mile. Hill Prince won comfortably enough by 1 1/2 lengths, and Middleground settled  for the place.

“He thought he needed the race,” Boland said, when asked why Hirsch ran him between the Derby and Preakness. “When you galloped him, he didn’t take anything out of himself, so that’s why he ran him a lot. He wanted to make sure he was dead fit.”

The Preakness the following week was contested over a slow track. A field of only six lined up, with Hill Prince the favorite at 7-10 and Middleground the 3.40-1 third choice behind Blue Grass winner and Kentucky Derby third Mr. Trouble, who started at 3.10-1.

“Mr. Hirsch said there wasn’t going to be much speed in here, so you might be laying closer,” Boland said.

Going into the first turn, Middleground was bumped and forced very wide by a longshot pacesetter, which allowed Hill Prince to shoot through along the inside to grab a big lead down the backside.

“At the three-eighths pole, I got within a couple lengths of (Hill Prince), but (the trip) took too much out of him,” Boland said. “He might have, should have, beaten him in the Preakness. It was just bad luck.

Hill Prince won by five lengths, with Middleground second in a pedestrian time of 1:59 1/5 over the wet going, a condition Middleground was no fan of. The score was now 3-1 in favor of Hill Prince.

The Belmont Stakes was run three weeks later and again Hill Prince was made the odds-on favorite. However, he had made an interim start, in the Suburban Handicap against older horses on Memorial Day, and ran third to Loser Weeper, while Middleground entered the “Test of the Champion” a fresher horse.

“That’s probably one of the easiest races I ever won. I never had to let him run an inch,” Boland said. “When the horses broke, Hill Prince was in front, and I kind of followed him going into the first turn, and I got through half the field. When I turned on the backside (Middleground) was laying fourth, and I just let him ease on from the half-mile pole to home and never let him have to run. He won easy.”

Indeed, the chart footnotes of the 1950 Belmont read: “MIDDLEGROUND was placed well up under fine rating in the first mile and it seemed apparent after that distance had been traversed that he could dominate the running at any time his rider chose.”

Unfortunately, recurring physical issues limited Middleground to just two more starts. He finished third in the Leonard Richards Stakes at Delaware Park and 10th to Hill Prince, who would be named Horse of the Year, in the Jerome Handicap at Belmont. He fractured a sesamoid during a workout in October and was retired.

Evan Shipman of the Morning Telegraph later wrote: “It is doubtful whether (Hirsch) ever got more out of a difficult charge than with Middleground. The colt’s 3-year-old campaign is a tribute to his own class and courage, and also to his trainer’s ability to achieve long-range objectives, working always under a serious handicap.

“If only his legs had been as stout as his heart!”

Sword Dancer

Boland’s next serious dalliance with Kentucky Derby glory came in 1959, the year he was honored by his fellow riders with the George Woolf Memorial Jockey Award. He picked up the mount on the Elliott Burch-trained Sword Dancer when Bill Shoemaker opted to remain on Tomy Lee, the English-bred winner of the Blue Grass.

A winner of a small stakes at Suffolk Downs as a 2-year-old, Sword Dancer improved enough during the course of the spring to finish a close second in the Florida Derby before winning a seven-furlong allowance at Churchill Downs a week before the Derby.

In the Derby, Tomy Lee rated in second before he grabbed a short lead after six furlongs. Sword Dancer was tracking in fourth until Boland could no longer hold him around the far turn.

“At the quarter pole he was wanting to run, so I let him ease on to the lead, and I hadn’t let him run yet,” Boland said. “We got in the stretch, and we had a little bumping around. I got a half-length in front of him, and then Tomy Lee came out and hit Sword Dancer in the middle and spun him in, like you would hit a car in the rear and turn him in. But Sword Dancer–he just got tired.”

In one of the more thrilling stretch duels in Derby history, Tomy Lee re-rallied inside Sword Dancer and won the photo by a nose, but Boland immediately claimed foul. The subsequent inquiry lasted more than 15 minutes, but the result stood.

Sword Dancer (outside) was denied victory by a nose in the 1959 Kentucky Derby (c) Churchill Downs

“(The chief steward) said, ‘You better be right. If you’re not right, you’re looking at 15 days or a long time on the ground,’” Boland said. “They didn’t suspend me, so I must have had a good claim.

“The first year I rode in the Derby, they called all the jocks in and they told us, ‘You know, we aren’t going to take a horse down in the Derby. It’s never been done. But if anybody causes any trouble, we’ll give you up to a year.’ So they weren’t going to take a horse down in the Derby unless it was really bad. I think they would now, but in those days they wouldn’t.”

Boland never again rode Sword Dancer, who was voted Horse of the Year, but he did get revenge on Tomy Lee. On the same afternoon Sword Dancer won the Belmont Stakes with Shoemaker up, Boland climbed aboard the filly Silver Spoon for the 1 1/8-mile Cinema Handicap at Hollywood Park. Tomy Lee, who skipped the final two legs of the Triple Crown, was the odds-on choice.

Silver Spoon with Boland up winning the 1959 Cinema Handicap at Hollywood Park (c) courtesy of the National Museum of Racing and Hall of Fame

Silver Spoon developed into America’s sweetheart in the lead-up to the Kentucky Derby. She won her first six starts, including the Santa Anita Derby over eventual Preakness winner Royal Orbit, by comfortable margins. However, she was only a lackluster third in the aforementioned Churchill allowance won by Sword Dancer. In the Derby she finished a respectable fifth, beaten just more than three lengths.

“She was some filly. She was a big, raw-boned filly,” Boland said.

The Cinema proved to be a mismatch, as Silver Spoon romped by nearly five lengths, with a weakly underpinned Tomy Lee sixth. Boland rode Silver Spoon twice more in stakes, finishing second in the Delaware Oaks to Resaca (a daughter of Middleground) and a distant third in the Monmouth Oaks to Royal Native, with whom she shared champion 3-year-old filly honors that season.

“She only liked California,” Boland said. “If you took her out of California, she wasn’t much.”

Asked if Silver Spoon was the best filly or mare he ever rode, Boland said no. That honor belonged to Alanesian, a brilliant 2-year-old of 1956 who was the top-weighted filly on the Experimental Free Handicap that season after winning all three starts, including the Spinaway at Saratoga by eight lengths and the Astarita at Belmont by two lengths.

The first significant runner for the powerful William Haggin Perry stable, Alanesian later made a notable impact in the breeding shed. In addition to the Hollywood Gold Cup-winning filly Princessnesian, Alanesian also reared Santa Anita Derby winner Boldnesian, the sire of Bold Reasoning who in turn sired 1977 Triple Crown winner Seattle Slew.

The 1959 Kentucky Derby and Cinema Handicap

Beau Purple and High Gun

Like his good friend Allen Jerkens, the late Hall of Fame trainer, Boland was no stranger to surprisingly deposing some of the leading Thoroughbreds in the country.

In the Sysonby Stakes at Belmont in September 1955, Boland secured the mount on High Gun, the previous year’s champion 3-year-old, when regular rider Eddie Arcaro opted for dual classic winner Nashua, who was coming in off his emphatic match race victory over Swaps in Chicago.

High Gun was a top-class 4-year-old, too. Regularly toting more than 130 pounds, he was a photo finish away from becoming the first horse since Whisk Broom II in 1913 to win the New York Handicap Triple of the Metropolitan, Suburban and Brooklyn.

“He was tough to train,” Boland said. “I know he was getting real sour. I went out and got on him one morning before the (Sysonby) to blow him out. Was going to work him a half-mile, and he refused to work. We were trying to get him to break off, and he wouldn’t.

“I took him back the wrong way at Belmont, over to the training track. He thought he was going to run off, and (I) let him run off, and he got his work in. He worked five-eighths of a mile.”

Over a sloppy track in miserable weather, High Gun rallied from more than eight lengths back in the field of five to win by a head, with Nashua a weakening third. It was High Gun’s last race, thus he forfeited a chance at Horse of the Year honors when Nashua came back to win the Jockey Club Gold Cup by five lengths.

“He would have won the Gold Cup and beat Nashua,” Boland said.

Boland’s most prolific victim, by far, was five-time Horse of the Year Kelso, whom he defeated three times aboard the Jerkens-trained Beau Purple.

“Funny horse. If he could get the first half-mile relaxed, he could beat anybody. And he would go two miles,” Boland said. “If he got geared up leaving the gate, then he wouldn’t finish.”

Beau Purple beat Kelso twice in 1962, in the Suburban Handicap and in the Man o’ War on turf, but Kelso returned the favor in the Woodward and finished ahead of the favored Beau Purple in the Washington D.C. International to claim Horse of the Year honors for the third time.

The final meeting between the two occurred in the 1 1/4-mile Widener Handicap at Hialeah in February 1963. Kelso entered off two preps, including a win in the nine-furlong Seminole Handicap, while Beau Purple was making his first start since the International in November.

“We ran an entry,” Boland recalled. “Kilmoray was a sprinter. I went to (jockey John) Rotz and I said, ‘Look, I’m going to split this stakes with you. This is what you have to do. You’re going to leave the gate like you’re going to go for the lead, because Kelso is going to be right next to you. If Beau Purple is in front, just pull him up, because he can’t go a mile and a quarter anyway.’

“(Jockey) Milo (Valenzuela on Kelso) really thought we entered a sprinter to set it up for Beau Purple, so when the man said ‘go,’ Beau Purple stumbled and Kilmoray went flying. Kelso was next to him. Milo then took back off Kilmoray, and it put Beau Purple on the lead.”

Beau Purple proceeded to set the slowest fractions in the history of the Widener and won by 2 1/4 lengths in his final start.

Boland later rode Kelso twice. In the great gelding’s 8-year-old debut, in June 1965 at Monmouth Park, Kelso was a fast-closing third in a six-furlong allowance. Boland was also aboard for Kelso’s 63rd and final start, at Hialeah in March 1966. Also a six-furlong allowance, Kelso finished a nondescript fourth and exited the race with a career-ending injury.

“He was all stoved up, and he wasn’t the old Kelso,” Boland said.

Lucien Laurin and Kauai King

Sixteen years after tasting classic glory twice with Middleground, Boland earned his final Triple Crown race victory in the 1966 Belmont Stakes with the Lucien Laurin-trained Amberoid.

Contested at Aqueduct while the Belmont grandstand was being rebuilt, this Belmont Stakes featured Kauai King’s bid for a Triple Crown sweep. Amberoid won the Wood Memorial but only ran sixth in the Kentucky Derby and third in the Preakness.

“I thought Kauai King would win the Triple Crown,” Boland said. “Amberoid was plodder-like.”

Amberoid and Bill Boland denied Kauai King the 1966 Triple Crown (c) Getty Images

Involved in an opening half-mile that went in :46 and change, Kauai King failed to see out the distance, while Amberoid proved to be the best stayer on the day. Amberoid collared Kauai King in upper stretch and won by more than two lengths as the 5-1 second choice. Finishing second was Buffle, owned by King Ranch and trained by Max Hirsch.

“I don’t suppose I had more than a couple of horses beat the first time past the stands, but when we reached the three-quarter pole on the backstretch, I had a running horse,” Boland told the Associated Press after the race. “When we got to the three-eighths pole, I honestly thought we’d win it, because (Kauai King) was swaying.”

The following year Boland picked up the mount aboard the fabulous Dr. Fager for the Woodward Stakes, when Braulio Baeza chose to remain on reigning Horse of the Year Buckpasser. The race also included the brilliant Damascus and at the time was dubbed the “Race of the Century.”

“Jerkens came to me and said, ‘(Dr. Fager) is not has his best now.’ He wanted me to go ride a horse of his at Atlantic City, a filly called Mac’s Sparkler.”

Boland stuck with Dr. Fager, a prescient choice, as Mac’s Sparkler wound up eighth in a sensational first edition of the Matchmaker Stakes. However, Dr. Fager was at a tactical disadvantage in the 1 1/4-mile Woodward, when the connections of both Damascus and Buckpasser entered rabbits, both to ensure a fast pace and to prevent Dr. Fager from stealing the race.

“(Trainer John) Nerud didn’t give me much orders. ‘Just don’t go head-and-head with these sprinters,’” Boland remembered. “They were on the outside of me, and when the man said ‘go,’ I was right with them. I’ll never forget (Ron) Turcotte (on Hedevar) and (Bobby) Ussery (on Great Power) sounding like two Indians screamin’ and hollerin’.”

In a rather anticlimactic event, given the pre-race hype, Dr. Fager was baited into setting a hot, contested pace and weakened. Damascus won by 10 lengths over Buckpasser, with Dr. Fager a half-length back in third. It was Boland’s only appearance on the back of the Hall of Famer.

“I was stupid…”

Only in his mid-30s in 1969, Boland decided to call it a career as a jockey and turn to training.

“I was stupid,” Boland said. “I should have ridden for another 10 years and set myself up. When Jerkens stopped riding me, I wasn’t doing any good. I kind of lost confidence in myself.

“I always wanted to train. It was a dumb move, but I did it. I did all right training.”

Boland’s career got off to a respectable start, when Native Fern, a 2-year-old he acquired from Hall of Fame trainer Woody Stephens, captured the Demoiselle Stakes at Aqueduct in the fall of 1969. Boland saddled more than 150 winners over 20 years, his most accomplished runner being multiple graded stakes winner Wise Philip.

Boland spent the final decade of his career in racing as an assistant steward and patrol judge at New York Racing Association tracks before he retired to Florida with his wife, Sandra. In 2006 the Hall of Fame came calling, nearly 40 years after his retirement from riding.

“I kind of gave it up (hoping to be inducted),” Boland said. “I think I was nominated three times, but didn’t make it. I had forgotten all about it, and then I got a call from there. They said, ‘Are you sitting down?’ I said, ‘No, but I will.’ ‘You just got inducted.’”

Fittingly, Jerkens introduced an emotional Boland into the Hall at that year’s ceremony.


Boland experienced some unbelievable highs on the racetrack, but also some truly terrible lows off of it. As recounted in a 2006 profile in the Lowell Sun to coincide with his Hall of Fame induction, Boland and his wife experienced the tragic loss of one grandson soon after birth, another grandson in a roadside accident, and a daughter, son-in-law and granddaughter in a 1990 house fire. The Bolands later raised another granddaughter, Jennifer, who was the lone survivor of the house fire.

“I love it,” said Boland of his retirement in Palm Coast, Fla., south of St. Augustine. “We live in a nice place here–nice town, play a lot of golf. I worked at a golf course here for about 10 years. Cart boy, starter and everything. Got free golf at two of the finest courses in America. The (Ocean Course at Hammock Beach) is like the Pebble Beach of the East, they say.”

A highly capable competitor on the links who reportedly shot his age not long ago, Boland said he’s never had a chance to play the most beautiful course he’s ever seen, Augusta National, but did have frequent access to a notable course in his riding days.

“I use to play Riviera when I was in California. Played it about 10 times every winter when I was out riding at Santa Anita,” he said. “I had a real good friend who was a member there, and he used to invite me over every Monday when there wasn’t racing.”

Boland says he’s only been back to the Kentucky Derby a few times, featuring as a guest speaker through a tour group arranged by a friend in California.

“It would be nice to be invited back there,” Boland chuckled.

For nearly seven decades Bill Boland’s name has been etched in Kentucky Derby and racing lore. He is one of the last remaining links to an era when Thoroughbred racing was not only the Sport of Kings, but, in terms of national popularity, also one of the Kings of Sport.

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2019 Kentucky Derby News & Notes

The Road to the Kentucky Derby series of points races ended with a bang when OMAHA BEACH recorded a one-length victory in the Arkansas Derby (G1) at Oaklawn Park.

Final works are all that remain as the contenders ready for the first Saturday in May at Chuchill Downs.

Stay tuned as it’s full speed ahead to the 145th running of the Kentucky Derby!

FREE Kentucky Derby PPs in points order courtesy of!






Kentucky Derby Championship Series

Arkansas Derby – Omaha Beach
Santa Anita DerbyROADSTER
Blue GrassVEKOMA
Wood Memorial – Tacitus
Louisiana DerbyBY MY STANDARDS
Rebel (1st Division) – Long Range Toddy
Rebel (2nd Division)OMAHA BEACH
Tampa Bay DerbyTACITUS
Fountain of YouthCODE OF HONOR
Risen Star – War of Will

Kentucky Derby Prep Season Races

El Camino Real Derby
Robert B. LewisMUCHO GUSTO
Springboard MileLONG RANGE TODDY
Los Alamitos FuturityIMPROBABLE
Kentucky Jockey ClubSIGNALMAN
Breeders’ Cup Juvenile – Game Winner
Breeders’ FuturityKNICKS GO
American PharoahGAME WINNER

European Road to the Kentucky Derby

Cardinal Condition Stakes – BYE BYE HONG KONG
Road to the Kentucky Derby Conditions Stakes – JAHBATH
Patton Stakes – PLAYA DEL PUENTE
Vertem Futurity TrophyMAGNA GRECIA
Prix Jean-Luc LagardereROYAL MARINE
Royal LodgeMOHAWK

Japan Road to the Kentucky Derby

Fukuyru Stakes – DER FLUG
Hyacinth Stakes – OVAL
Zen-Nippon Nisai YushunNOVA LENDA
Cattleya ShoMAKE HAPPY

PHOTO: Kentucky Derby Trophy (c) Coady Photography/Churchill Downs

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Sir Barton and Johnny Loftus

There was no model for Sir Barton


But none before Sir Barton had ever attempted, much less won, the premier stakes for three-year-olds held in the major racing centers of Kentucky, Maryland, and New York.


There was no model for Sir Barton’s success. There, of course, had been a number of three-year-olds before him which had left a lasting imprint on the history of the turf, and to this day some would objectively be considered finer runners. But none before Sir Barton had ever attempted, much less won, the premier stakes for three-year-olds held in the major racing centers of Kentucky, Maryland, and New York.

Two thousand nineteen marks the centenary of Sir Barton’s entree into American turf lore, but even that wasn’t immediately apparent at the time. As is well known, the linking of the Kentucky Derby, Preakness, and Belmont Stakes into a cohesive series horsemen wanted to win came more than a decade later. The concept of an American Triple Crown was widely attributed to famed turf writer Charles Hatton and Sir Barton’s admittance into its pantheon was strictly retroactive.

In many respects, 1919 was also Year One for the Triple Crown as we know it, minus modifications for dates and distances. While decades old, the Kentucky Derby had only just begun to gain true acceptance from the sport’s Eastern pillars, largely stemming from Harry Payne Whitney’s exultation at his filly Regret’s victory in 1915.

The Preakness, which the Maryland Jockey Club acknowledged at the time only dated to 1909 (the so-called “lost Preaknesses” weren’t “discovered” until much later), was the proverbial new kid on the block, but by 1919 it was the most lucrative race for three-year-olds contested in the east with a purse of $30,000.

The Belmont Stakes, founded in 1867 and closest in equivalency to England’s Derby at the time, had long maintained its prestige despite lean years earlier in the decade when it was blacked out along with the rest of the sport in New York for a short time. However, its supremacy began to be seriously challenged from Kentucky and Maryland, where the existence of pari-mutuel wagering presumably provided an infusion of purse money the then bookmaker-dominated New York circuit could not immediately match.

A most unlikely pioneer

the timing seemed right for American racing to enter a new era

In other words, the timing seemed right for American racing to enter a new era, much like the world in general had following the previous fall’s armistice ending The Great War.

Sir Barton was a most unlikely pioneer. A roguish colt, he was a half-brother to Sir Martin, the beaten favorite in the 1909 Epsom Derby when he lost his rider around Tattenham Corner. Sir Barton raced four times – all in stakes – for co-breeder John E. Madden, who sold the underachieving son of Star Shoot to Commander J. K. L. Ross for $10,000 after Sir Barton failed to earn a penny in the Tremont, Flash, United States Hotel, or Sanford Memorial Stakes.

Ross, heir to the Canadian Pacific Railway, “purchased any likely looking runner he happened to see,” wrote William H. P. Robertson in “The History of Thoroughbred Racing in America.” His private trainer was Guy Bedwell, a seven-time champion trainer who had also been the nation’s leading owner in 1916 before dispersing his stable to work for Ross.

While Sir Barton struggled to prove himself any type of runner, the gelding Billy Kelly was a proven winner when Ross acquired him early in the 1918 Saratoga meet. A six-time winner in his first eight starts, he would win eight of his next nine races for Ross, including the Flash, United States Hotel, and Sanford Memorial that Sir Barton would lose by a combined margin of 50 1/2 lengths.

Sir Barton’s margin of defeat in his debut for Ross in the Hopeful Stakes is unknown, but it was significant. Eternal, who would go on to defeat Billy Kelly in the McLean Memorial at Laurel later in the fall, won by three lengths, with an eight-length gap between the second- and third-place finishers. Sir Barton came home 16th in the field of 20.

The one true sign of life Sir Barton showed as a juvenile came in his season finale when, re-outfitted with blinkers, he finished second in the Futurity Stakes over a straight six furlongs at Belmont Park. He missed the remainder of the season after developing abscesses caused from a kick by a stablemate. Thus, Sir Barton entered his winter quarters still a maiden but having recouped some of Ross’ investment.


The 1919 Kentucky Derby was held on May 10, with Eternal and Billy Kelly the horses to beat. Eternal had won his only prep at Oaklawn Park, while Billy Kelly had racked up two wins at Havre de Grace in Maryland. Strange as it might seem to modern eyes, Eternal, Billy Kelly, and Sir Barton, who did not prep at all, tackled the 1 1/4-mile Derby without having raced beyond six furlongs.

Eternal was the 2.1-1 favorite in the Derby, with the entry of Billy Kelly and Sir Barton at 2.6-1. While the historical consensus over the years has been that Sir Barton was more or less entered as a “rabbit” for the more accomplished Billy Kelly, a race-day news wire preview noted that:

“Billy Kelly is said to be at his best, but many doubt his ability to negotiate the Derby distance at top form. It is understood Sir Barton is the main reliance of the Ross stable.”

In receipt of a significant weight allowance due to his maiden status, Sir Barton broke on top, repelled challenges from both Eternal and Billy Kelly, and drew off late to win by five lengths under Johnny Loftus. The final time over a heavy track was a pedestrian 2:09 4/5. Billy Kelly finished second, making Ross the first person in history to own the top two finishers in a Kentucky Derby. The stable earned $23,325.

The 1 1/8-mile Preakness was scheduled just four days later. Forming an entry with Sir Barton was the filly Milkmaid, but she proved no factor as Sir Barton went to the front end again and won eased up by four lengths over Eternal. The 7-5 favorite, Sir Barton won under scale weight of 126 pounds in a time of 1:53 over a fast track and earned Ross another $24,500.

“Loftus says Sir Barton is the best horse he ever rode and this is a plenty, as Johnny has kicked many a good one in his time,” noted the Thoroughbred Record. That opinion undoubtedly changed months later when Loftus piloted through 10 wins from 11 starts a brilliant juvenile named Man o’ War.

In a move later repeated by Omaha, Whirlaway, Count Fleet, and Citation, Sir Barton made one start in between the Preakness and Belmont Stakes. Again facing his old foe Eternal, Sir Barton won the one-mile Withers Stakes at Belmont Park eased up by 2 1/4 lengths.

In the 1 3/8-mile Belmont Stakes on June 11, Sir Barton faced only two others. Indulging pacesetter Natural Bridge, Sir Barton seized the lead after entering the main course on a much differently configured Belmont track of the day and won comfortably by five lengths. The 7-20 favorite finished in 2:17 2/5, a new American record. The winner’s share was approximately half that of the Kentucky Derby and Preakness at $11,950.

“I only let him run an even eighth of a mile at the top of the stretch,” Loftus was quoted by Daily Racing Form, suggesting Sir Barton could have shattered the distance record by more if given the chance.

Sir Barton proved a very good horse if not an all-time great. He won four of his remaining nine starts at three, and in 1920 won four stakes in 12 starts. His most notable win that season was the Saratoga Handicap, in which he beat the famed gelding Exterminator by two lengths while giving “Old Bones” three pounds in track-record time of 2:01 4/5 for 1 1/4 miles.


Race of the Ages - Sir Barton vs Mano' War

Race of the Ages – Sir Barton vs Man o’ War on Nov. 2, 1920
(Wikimedia Commons / Educational Films Corporation of America / Educational Film Exchanges)

Sir Barton’s most famous appearance as a four-year-old was in the $75,000 Kenilworth Park Gold Cup in Windsor, Ontario, a 1 1/4-mile match race between him and Man o’ War. Wagering reflected the ostensible mismatch as Man o’ War started at 1-20 with Sir Barton at 5.55-1. “Big Red” easily defeated the only older horse he would ever face by seven lengths. Sir Barton was retired after suffering two more losses at Pimlico, concluding his career with a record of 31-13-6-5, $116,857.

Sir Barton sired eight stakes winners, most notably 1928 Kentucky Oaks winner Easter Stockings. He ended his days in Douglas, Wyoming, where he died in 1937. His remains lie in a small community green called Washington Park.

Sir Barton’s feat and place in history is the subject of a soon-to-be published biography from the University Press of Kentucky, “Sir Barton and the Making of the Triple Crown” by Jennifer S. Kelly. A century after an initial underachiever eventually blossomed and planted the seed that would become American racing’s popular annual narrative, a fuller account of his life and significance seems most proper.

(Sir Barton and Johnny Loftus Photo Courtesy of Wikimedia Commons)

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Bellafina keeps options open with Triple Crown nomination

Kaleem Shah’s star filly Bellafina is expected to remain in her own division on the path toward the Kentucky Oaks (G1), but connections have retained the option of taking on males.

The Simon Callaghan trainee was nominated to the Triple Crown by the deadline this past Saturday, and she’s been added to the nominations for the April 6 Santa Anita Derby (G1) as well.

Before getting too far ahead of ourselves, however, the current plan is still to stick to the Oaks trail.

“Fillies for the moment,” Callaghan said. “Just wanted the option.”

The leading two-year-old filly of 2018 going into the Breeders’ Cup, Bellafina thrashed her rivals in the Sorrento (G2), Del Mar Debutante (G1), and Chandelier (G1). She was accordingly dispatched as the 9-5 favorite in the Juvenile Fillies (G1) at Churchill Downs, only to run an uncharacteristic fourth, and subsequently found to be in season.

Returning to action with a breathtaking display in the January 6 Santa Ynez (G2), Bellafina served notice that she could be even better this year. Indeed, the strapping daughter of Quality Road – sire of Saturday’s Pegasus World Cup (G1) winner City of Light and 2017 Oaks champion Abel Tasman – is entitled to progress with maturity.

And that’s food for thought. The “Should Bellafina join the Kentucky Derby (G1) trail” discussion figures to gain steam if she romps in her next race, likely the February 9 Las Virgenes (G2).

Yet even if the Triple Crown option is left unexplored, Bellafina could be just the type to try her mettle versus the boys later on in her career.

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