Phenom to Journeyman: The Riding Life of Bill Boland

April 24th, 2019

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.