Live Oak’s homebred Win Win Win earned his way into the Kentucky Derby (G1) field with his third-place finish in the Tampa Bay Derby (G2), and most recently, a runner-up performance in the Blue Grass Stakes (G2) at Keeneland. The Florida-bred has 50 points on the Road to the Kentucky Derby series, which has him in 16th place on the Leaderboard.

Win Win Win is by the Japanese-bred champion sprinter Hat Trick, who was a multiple Group 1 winner and came out on top in the 2005 Hong Kong Mile (G1). Hat Trick has sired at least 34 stakes winners and two champions from nine crops to date. His top progeny have been most successful in South America, though he has had some success in North America, as well.

Hat Trick is by Horse of the Year Sunday Silence, winner of the 1989 Kentucky Derby, Preakness Stakes (G1) and Breeders’ Cup Classic (G1). As good as the son of Halo was during his racing days, the impact Sunday Silence has made in the Japanese breeding shed has been remarkable. He was Japan’s leading sire from 1995 -2007, and he has also been mightily successful as a sire of sires and as a broodmare sire.

The first dam of Win Win Win is the winning Smarty Jones mare Miss Smarty Pants, who counts herself a half-sister to Grade 3 queen Unbridled Humor. Smarty Jones, winner of the 2004 Kentucky Derby and Preakness, has not been as productive in the breeding shed as he was on the racetrack, however. The champion son of Elusive Quality is the broodmare sire of nine stakes winners to date, with overall earnings in excess of $5.9 million.

Win Win Win is an interesting sort in that his maternal and paternal grandsires found glory in each of the first two legs of the Triple Crown. The colt was full of run in the latter stages of the Bluegrass Stakes in his first attempt going 1 1/8 miles, and his female line has stamina influences through the likes of Unbridled, Caveat and Northern Jove.

The talented Kentucky Derby prospect has had trouble overcoming poor starts in a few races this campaign, which could be his undoing in a 20-horse field on May 4.

PHOTO: Win Win Win captures the Pasco Stakes under jockey Julien Pimentel at Tampa Bay Downs on January 19, 2019 (c) SV Photography

Wertheimer et Frere’s homebred Spinoff finished a close second in the Louisiana Derby (G2) to earn his spot in the starting gate of the Kentucky Derby (G1) on May 4. The Todd Pletcher trainee was the last sophomore to gain a berth after garnering 40 points on the Road to the Kentucky Derby series.

Spinoff has run well in each of his four lifetime appearances. The chestnut owns two wins with a pair of placings, having run third in the Saratoga Special Stakes (G2) in his juvenile finale.

The improving contender was bred in the Bluegrass State and is by excellent sire Hard Spun, who finished runner-up in the 2007 Kentucky Derby (G1) and Breeders’ Cup Classic (G1). The son of Danzig has been a sire who has passed on brilliance and stamina to many of his offspring, and he accounts for at least 70 stakes winners from nine crops to have raced.

Spinoff’s first dam is the Gone West mare Zaftig, who was a dominant heroine of the 2008 Acorn Stakes (G1) at Belmont Park. The gray concluded her six-race career with a third-place finish in the second running of the Breeders’ Cup Filly & Mare Sprint.

Zaftig counts herself as a half-sister to 2012 Mother Goose Stakes (G1) queen Zo Impressive, who was also second-best in that year’s Acorn and Coaching Club American Oaks (G1). She, like Spinoff, is by Hard Spun.

The second dam of Spinoff also achieved Grade 1 glory. The Cozzene mare Zoftig bagged the 2000 Selene Stakes (G1) at Woodbine while also finishing second by a nose in the Ashland Stakes (G1) at Keeneland.

Gone West has been among the leading global broodmare sires for years. His daughters have produced in excess of 140 stakes winners, with earnings eclipsing $83 million in total. They have produced Grade and Group 1 winners across the globe, with at least eight individual champions among them.

Spinoff has improved his BRIS Speed number in every lifetime performance (82-89-93-102), but he does have two major obstacles to overcome in my opinion. First, he has run just twice since August, which could leave him a bit short for the first leg of the Triple Crown. Secondly, his regular rider, John Velazquez, has opted to ride one of his foes for the Run for the Roses.

Nonetheless, Spinoff has the pedigree and, perhaps, the ability, to succeed running 1 1/4 miles at Churchill Downs on May 4.

PHOTO: Spinoff finishes second in the Louisiana Derby (G2) at Fair Grounds (c) Hodges Photography/Lou Hodges Jr.

Wachtel Stable, Eclipse Thoroughbred Partners and Gary Barber’s Gray Magician punched his ticket to the Kentucky Derby (G1) following a runner-up finish in the U.A.E. Derby (G2) at Meydan on March 30. The sophomore picked up 41 total points on the Road to the Kentucky Derby and ranks 18th on the leaderboard.

Gray Magician was bred in Kentucky by Twin Creeks Farm, and he was an $18,000 RNA at the 2017 Fasig-Tipton Kentucky July yearling sale. He is by the once-beaten Graydar, who earned his most notable victory in the 2013 Donn Handicap (G1) at Gulfstream Park.

From a trio of crops to have raced, that son of Unbridled’s Song is the sire of a trio of stakes winners including 2018 Robert B. Lewis Stakes (G3) winner Lombo, who is a full brother to Gray Magician.

Gray Magician was produced from the stakes-winning Johannesburg mare Burg Berg, who is responsible for an unnamed two-year-old colt by Constitution, as well as an unnamed yearling filly by Street Boss. His second dam is stakes winner Snowberg, who placed in six graded races including three of the Grade 1 variety. Both of these mares did their best work at sprint and middle distances.

Johannesburg was an unbeaten juvenile who capped his spectacular two-year-old season in the 2001 Breeders’ Cup Juvenile (G1) at Belmont Park. He has been solid at stud and as a broodmare sire as well, where his daughters have produced at least 36 stakes winners, four of whom were champions, with total earnings in excess of $26 million. The top domestic runner out of a Johannesburg mare is Grade 1 victor Collected, who was runner-up in the 2017 Breeders’ Cup Classic (G1).

Gray Magician will enter the Run for the Roses as one of the longest shots in the field. He lacks a stakes win, his pedigree is geared for middle distances, and the class of the U.A.E. Derby field is in question.

In addition, the gray colt will have to overcome his lengthy round-trip voyage to Dubai and run a peak race at Churchill Downs to threaten a deep Kentucky Derby cast. A top performance at 1 1/4 miles from Gray Magician would be a big surprise to me.

PHOTO: Gray Magician at Meydan (c) Dubai Racing Club/Neville Hopwood

Mrs. J. V. Shields Jr., E. J. M. McFadden Jr. and LNJ Foxwoods’ Country House finished third in the Arkansas Derby (G1) most recently to earn his spot in the starting gate of the Kentucky Derby (G1) at Churchill Downs. The chestnut colt previously finished second in the Risen Star Stakes (G2) and fourth in the Louisiana Derby (G2), as he has amassed 50 points on the Road to the Kentucky Derby.

Trained by Bill Mott, Country House was bred in the Bluegrass State by J. V. Shields Jr. and is by champion sire Lookin at Lucky, who finished sixth as the favorite in the 2010 Kentucky Derby. He has sired at least 42 stakes winners from six crops to date, notably champions Accelerate and Wow Cat.

Country House’s first dam is the winning War Chant mare Quake Lake, making him a half-brother to recent Albert M. Stall Memorial Stakes heroine Mitchell Road. Quake Lake herself is a half-sister to Grade 3 victor and Canadian classic hero Breaking Lucky, who is also by Lookin at Lucky and was runner-up in the 2016 Clark Handicap (G1).

The excellent War Chant was a three-time graded winner during his sophomore season, capping his career with an ultra-impressive tally in the 2000 Breeders’ Cup Mile (G1) at Churchill Downs. As a broodmare sire, daughters of War Chant have produced at least 19 stakes winners with overall earnings exceeding $18 million.

Country House has a pedigree that is slanted towards turf in my opinion, and his stakes-winning half-sister can attest to that. While he was unplaced in his debut on the lawn, the sophomore could eventually thrive on the green with his lineage and running style.

The contender has been consistent this spring, displaying a solid late kick in his four 2019 assignments. The robust three-year-old has a quartet of route races under him this season and he should be as fit as any runner in the Kentucky Derby field. He still has a lot of ground to make up on the top players in the cast, however, and he looks like a Triple Crown outsider to me at this stage of his development.

PHOTO: Country House readies for the 145th Kentucky Derby under the Twin Spires at Churchill Downs (c) Coady Photography/Churchill Downs

Speedway Stable LLC’s Roadster rallied to take the Santa Anita Derby (G1) and earned 100 points on the Road to the Kentucky Derby (G1). The once-beaten colt will head to Churchill Downs as one of the favorites to capture the Run for the Roses.

Trained by Bob Baffert, the gray three-year-old was a stylish winner on debut at Del Mar in the summer, and he concluded his brief juvenile campaign with a third-place finish in the Del Mar Futurity (G1). He closed swiftly to conquer allowance foes at Santa Anita Park in his three-year-old bow, which preceded his biggest win to date.

Roadster was bred in Kentucky by Stone Farm, and he was purchased by his current owners for $525,000 at the 2017 Keeneland September Yearling Sale.

The Kentucky Derby (G1) contender is by 2009 Florida Derby (G1) hero Quality Road, who has sired at least 34 stakes winners to date. The rising stud is responsible for champions City of Light and Caledonia Road, as well as three-time Grade 1 heroine Bellafina, the current favorite for the Kentucky Oaks (G1) on May 3.

Roadster’s first dam is the Silver Ghost mare Ghost Dancing, who capped a successful career with a victory in the Oakley Stakes at Colonial Downs. The speedy gray won five times with a pair of runner-up efforts from nine lifetime performances.

Ghost Dancing has also been productive at her new craft. Her first offspring resulted in the Grade 3-placed Moro Tap, and her third foal, Ascend, captured the 2017 Manhattan Stakes (G1) at Belmont Park. She has also produced an unnamed yearling colt by Candy Ride.

Silver Ghost has been solid and versatile as a broodmare sire. While he was a sprinter during his career and many of his top progeny have been one-turn types, the son of Mr. Prospector dons a fine catalog page. His dam, the Halo mare Misty Gallore, won five graded races while checking in second in the Beldame Stakes (G1) and Ruffian Handicap (G1). She is a half-sister to Irish champion Minstrella.

His daughters are responsible for at least 56 stakes winners, who have banked in excess of $47 million. 2000 Hopeful Stakes (G1) star Yonaguska; multiple graded stakes winner and sire Salute the Sarge; five-time Grade 3 victor Silverfoot; and 2015 Turf Classic Stakes (G1) winner Finnegans Wake are some of the top runners out of daughters of Silver Ghost.

Roadster has a lot of room for improvement with just four starts under his belt. The colt answered the nine-furlong question correctly in the Santa Anita Derby while appearing to have more left in the tank at the finish.

I don’t envision that his pedigree will hold him back from enduring 1 1/14 miles at Churchill Downs on May 4. And being under the care of Kentucky Derby savant Bob Baffert will undoubtedly aid his chances to peak on the big day. Roadster is an obvious Triple Crown contender to me.

© BENOIT PHOTO: Roadster (outside) and jockey Mike Smith overpower Game Winner (inside) under Joel Rosario to win the Santa Anita Derby (G1) on April 6, 2019, at Santa Anita Park

Gary Barber’s War of Will earned 60 points on the Road to the Kentucky Derby series and sits in 12th place on the leaderboard in anticipation of his Run for the Roses on May 4. The Mark Casse trainee is a two-time graded stakes winner this campaign and he looks like an interesting longshot in his chase for Derby glory.

War of Will was Grade-1 placed on the lawn as a juvenile and concluded his creditable two-year-old season with a maiden win at Churchill Downs while making his dirt debut. The Kentucky-bred appreciated the surface change and rolled home to convincing wins in both the Risen Star Stakes (G2) and Lecomte Stakes (G3) at Fair Grounds to start 2019.

The colt was bred in the Bluegrass State by Flaxman Holdings Ltd. and fetched a bid of $298,625 at the Arqana Breeze-Up Sale at Deauville from Justin Casse. He is by top global sire War Front, who from 10 crops to race is responsible for more than 80 stakes winners and eight individual champions. His progeny have been wildly successful both in the United States and abroad, performing at the highest level on any surface they race upon.

War Front is by the remarkable Danzig and out of the stakes-winning Rubiano mare Starry Dreamer. This makes him a half-brother to dual Grade 2 queen Teammate, multiple Grade 3 victor Ecclesiastic and stakes star Riviera Cocktail.

War of Will is out of the stakes-winning Sadler’s Wells mare Visions of Clarity. He is a half-brother to Group 1 winner Pathfork, as well as two-time stakes hero Tacticus (not to be confused with Wood Memorial [G2] star Tacitus).

Visions of Clarity counts herself as a half-sister to the brilliant Spinning World, who concluded his sensational career by conquering the 1997 Breeders’ Cup Mile (G1) and was twice named a European champion. This outstanding female line traces back to foundation mare Best in Show, the 1982 Broodmare of the Year.

War of Will is bred to be great and he has looked the part on a few occasions during his sophomore season. The three-year-old bay had a major hiccup in the Louisiana Derby (G2) most recently when finishing ninth, though he has trained swiftly following his Fair Grounds flop and his oft-conservative conditioner wouldn’t point him towards Churchill Downs unless the colt was fit and healthy.

The Kentucky Derby contender has an abundance of class throughout his bloodlines and 1 1/4 miles should be within his scope if he is good enough.

PHOTO: War of Will wins the Risen Star Stakes (c) Holly M. Smith Photography

Imperial Racing LLC’s Plus Que Parfait punched his ticket to the Kentucky Derby (G1) with a score in the U.A.E. Derby (UAE-G2). The sophomore sits in fourth place on the Road to the Kentucky Derby leaderboard with 104 points.

The chestnut started his career on the turf at Ellis Park as a juvenile and finished third at first asking. He graduated in his third effort in a maiden special weight event at Keeneland and capped his two-year-old season by finishing a closing second in the Kentucky Jockey Club Stakes (G2).

Plus Que Parfait started 2019 slowly, though, finishing off-the-board in both the Lecomte Stakes (G3) and Risen Star Stakes (G2). His triumph at Meydan was a fine form reversal, but his class remains in question due to the pair of subpar showings at Fair Grounds.

He was bred in the Bluegrass State by Calloway Stables LLC and passed through the sales ring on a pair of occasions. The youngster was an RNA for $24,000 at the 2016 Keeneland November Breeding Stock Sale prior to bringing the gavel down at $135,000 at the 2017 Keeneland September Yearling Sale.

The contender is by Point of Entry, who has sired six stakes winners from a trio of crops to have raced. 2018 Breeders’ Cup Mile (G1) third Analyze It is among his top performers to date.

The first dam of Plus Que Parfait is the unplaced Awesome Again mare Belvedera, who counts herself as a half-sister to 1999 Canadian Oaks starlet Touch Dial. This is the same female line that produced three-time Australian Group 1 winner Toldeo.

Awesome Again has been a very productive broodmare sire, as his daughters are responsible for at least 71 stakes winners and have banked more than $62 million overall. Five individual champions are among those, led by 2018 Breeders’ Cup Classic (G1) hero Accelerate.

His second dam is the Badger Land mare Forever Land, winner of the 1991 Astoria Stakes (G3). She was a sprinter who never built on her two-for-two juvenile campaign, garnering just one more tally in her final 14 starts.

Plus Que Parfait does not boast the deepest catalog page in the Kentucky Derby field. He is far from a blue-blood and there are speed influences through the first few generations of his female line.

The ridgling did finish well going 1 3/16 miles at Meydan, though the overall quality of that field is debatable. He will be hard pressed to improve off of that performance facing 19 foes going 1 1/4 miles at Churchill
Downs.

Plus Que Parfait appears to be a Kentucky Derby outsider.

PHOTO: Plus Que Parfait and jockey Jose Ortiz win the U.A.E. Derby (G2) at Meydan on March 30, 2019 (c) Dubai Racing Club/Mathea Kelley

Fox Hill Farms Inc.’s Omaha Beach picked up his second consecutive graded stakes win following a one-length tally in the Arkansas Derby (G1). The colt has earned 137.5 points on the Road to the Kentucky Derby (G1) and will vie for favoritism at Churchill Downs on May 4.

Omaha Beach raced on the lawn in his first trio of outings as a juvenile and hit the board on each occasion. The Richard Mandella trainee was switched to the dirt for his three-year-old debut and checked in a sharp second at Santa Anita Park. A nine-length maiden victory followed, and the dark bay colt then captured the Rebel Stakes (G2) when topping unbeaten champion Game Winner by a measured nose.

The colt was bred in the Bluegrass State by Charming Syndicate, and he didn’t meet his reserve after a final bid of $625,000 at the 2017 Keeneland September Yearling Sale. He was purchased privately after the sale by his current owner.

Omaha Beach is by top sire War Front, who has celebrated great success on both sides of the ocean. From 10 crops to date, War Front has sired eight individual champions and more than 80 stakes winners. The son of Danzig is well represented for the Kentucky Derby (G1) with Omaha Beach and Risen Star Stakes (G2) victor War of Will.

Omaha Beach is out of the winning Seeking the Gold mare Charming, who counts herself a half-sister to champion Will Take Charge as well as 2012 Florida Derby (G1) star Take Charge Indy. Omaha Beach was preceded in Grade 1 glory by his half-sister, champion and 2014 Breeders’ Cup Juvenile Fillies (G1) heroine Take Charge Brandi.

His second dam is the Dehere mare Take Charge Lady, who was the 2013 Broodmare of the Year. She was also a multiple Grade 1 winner who finished second in the 2002 Kentucky Oaks (G1).

Dehere has been an outstanding broodmare sire. His daughters have produced more than 100 stakes winners, including champions Will Take Charge, Long Train Running and Midnight Lute. Pegasus World Cup Invitational (G1) star City of Light, and Grade 1 winner and sire Graydar, are also out of Dehere mares.

Omaha Beach is from a rapidly evolving female line and his sire is among the best at his craft. The sophomore has been finishing off his route races like a colt that will not have distance limitations. And his connections are as likable as any in the thoroughbred industry, in my opinion.

I believe Omaha Beach possesses all the tools to be crowned a Kentucky Derby winner.

PHOTO: Omaha Beach captures the Arkansas Derby (G1) at Oaklawn Park on April 13 under jockey Mike Smith (c) Coady Photography/Oaklawn Park

R. A. Hill Stable and Gatsas Stables’ Vekoma earned a berth in the starting gate at Churchill Downs on May 4 with a convincing tally in the Blue Grass Stakes (G2) at Keeneland. The once-beaten colt earned 100 points on the Road to the Kentucky Derby to book his spot in the starting gate for conditioner George Weaver.

The Blue Grass winner was bred in Kentucky by Alpha Delta Stable LLC. He was purchased for $135,000 at the 2017 Keeneland September Yearling Sale from the Lane’s End consignment.

Vekoma is by top sire Candy Ride, who is also represented on the Derby Trail through his son, champion Game Winner. Candy Ride’s popularity has grown in recent years, in part due to the success of Horse of the Year and near $16 million earner Gun Runner. In total, progeny of Candy Ride have amassed at least 83 stakes wins to date.

Vekoma’s first dam is the Speightstown mare Mona de Momma, who was victorious in the 2010 Humana Distaff Stakes (G1) at Churchill Downs and Las Flores Handicap (G3) at Santa Anita Park. Mona de Momma was a one-turn specialist who finished well back in her lone route attempt.

Eclipse Award winner Speightstown was a brilliant racehorse who concluded his career with a convincing score in the 2004 Breeders’ Cup Sprint (G1) at Lone Star Park. The son of Gone West has been a good broodmare sire, with his daughters producing at least 20 stakes winners to date, though the majority of those have ben sprinter/miler types.

The second dam of Vekoma is the Linkage mare Society Gal, who is a half-sister to a pair of stakes winners including influential sire Mr. Greeley. This is the same female line as multiple Grade 1 queen Paradise Woods as well as 2007 Kentucky Derby (G1) and 2006 Breeders’ Cup Juvenile (G1) star Street Sense.

Vekoma has done little wrong to date with three wins and a good third from four lifetime tries. The Kentucky-bred chestnut was much the best at Keeneland in his debut at nine furlongs, and the colt might be able to carve out 1 1/4 miles under the right circumstances.

However, I think his questionable action combined with a pedigree that is geared towards middle distances, will make the 10-furlong voyage in a 20-horse field at Churchill Downs a huge obstacle for him.

Vekoma is clearly one of the more talented horses in his generation, but I feel that he will be a cut below at the Kentucky Derby distance.

PHOTO: Vekoma and jockey Javier Castellano win the Blue Grass Stakes (G2) at Keeneland on April 6, 2019 (c) Coady Photography/Keeneland

Gary and Mary West’s homebred Maximum Security earned 100 points on the Road to the Kentucky Derby following his wire-to-wire tally in the Florida Derby (G1) at Gulfstream Park. The Jason Servis trainee improved to an unbeaten four-for-four after his 3 1/2-length triumph beneath Luis Saez.

Maximum Security is the first graded winner by 2013 Breeders’ Cup Juvenile (G1) hero New Year’s Day. By the brilliant Street Cry, New Year’s Day is a half-brother to 2016 Fountain of Youth Stakes (G2) victor Mohaymen, as well as 2019 El Camino Real Derby runner-up Kingly.

Maximum Security’s dam is the winning Anasheed mare Lil Indy, who is also responsible for an unnamed yearling colt by Flashback. Lil Indy counts herself as a half-sister to three-time Grade 1 victor and sire Flat Out, who won back-to-back editions of the prestigious Jockey Club Gold Cup (G1) at Belmont Park in 2011-12.

Anasheed has had little impact as a broodmare sire in North America, though he has yet to be given a serious chance in the states. The well-bred son of A.P. Indy was sold to Russian interests for stud duty in 2010, but he hails from one of the classier families in racing.

His first dam is European champion Flagbird, one of seven stakes winners produced by Grade 2 queen Up the Flagpole. This immediate female line includes an honor roll consisting of Horse of the Year Mineshaft and his dam, two-time Grade 1 queen and Broodmare of the Year Prospector’s Deelite; multiple Grade 1 heroine Tomisue’s Delight; Grade 1 star Mr. Sidney; 2008 Ashland Stakes (G1) winner and Kentucky Oaks (G1) runner-up Little Belle; 2017 Jenny Wiley Stakes (G1) victress Dickinson; 2013 Louisiana Derby (G3) star Revolutionary; etc.

Maximum Security is by a $5,000 stallion and has a broodmare sire who has yet to impact racing in the United States. In addition, he also began his career at the modest $16,000 maiden claiming level.

But make no mistake – the Kentucky Derby contender has an intriguing bloodline. It’s more than conceivable that he will withstand the 10 furlongs at Churchill Downs on May 4. The unbeaten sophomore finished fast going 1 1/8 miles in his final Derby prep to indicate that he might not have distance limitations.

I think Maximum Security is among the most fascinating horses on the Triple Crown trail.

PHOTO: Kentucky Derby contender Maximum Security posting a convincing win in the Florida Derby (c) Adam Coglianese Photography