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Kentucky Derby Pedigree Profile: Win Win Win

By John Mucciolo

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

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