Live Oak Retires Win Win Win

Live Oak Plantation's grade 1-winning homebred Win Win Win has been retired from racing due to a tendon injury, the farm announced Sept. 28. Stud plans will be announced at a later date.

A versatile 4-year-old son of grade 1 winner Hat Trick, Win Win Win was rounding into the best form of his career for trainer Michael Trombetta, having most recently won the Forego Stakes Presented by America's Best Racing (G1) at Saratoga Race Course. He was being aimed for the Big Ass Fans Breeders' Cup Dirt Mile (G1) at Keeneland.

"I would like to thank Mike Trombetta and his staff and the Live Oak Stud crew for all the care they gave Win Win Win," said Live Oak's Charlotte Weber. "He provided us a lot of thrills on the racetrack, and I am looking forward to his future as a stallion."

In a deep and contentious Forego, Win Win Win circled the field at least eight-wide around the turn and finished with a dramatic flourish, going from last to first in the seven-furlong event to win in 1:21.71, leaving in his wake four grade 1 winners—Complexity, Whitmore, Mind Control, and Firenze Fire.

Last season at 3, Win Win Win set a track record at Tampa Bay Downs in the Pasco Stakes where he drew off with authority in the seven-furlong test. He sped to an eye-catching 7 1/4-length score in the stakes and track-record time of 1:20.89, smashing the previous record of 1:21.40 set by Catalina Red in the 2014 renewal of the Pasco and equaled by Grande Rojo the following year. He went on to finish third in the Lambholm South Tampa Bay Derby (G2) and second in the Toyota Blue Grass Stakes (G2), which earned him a shot in the Kentucky Derby Presented by Woodford Reserve (G1), where he finished ninth. Win Win Win would finish off the board in the Preakness Stakes (G1) before finding redemption in New York.

Demonstrating his versatility, Win Win Win captured the Manila Stakes at one mile on turf at Belmont Park where his final time of 1:31.56 was a few ticks shy of the 1:31.23 track record set by Oscar Performance  in 2018.

Win Win Win won two of his three starts at 2 and became stakes-placed with a runner-up finish in the seven-furlong Heft Stakes at Laurel Park. He ended his career with five wins out of 12 starts and six wins or places in black-type stakes. He earned $601,600 in purses.

Live Oak bred Win Win Win out of the winning Smarty Jones mare Miss Smarty Pants, a half sister to graded stakes winner and multiple stakes producer Unbridled Humor (Distorted Humor ). The family also includes multiple graded-placed stakes winner Icy Warning (Caveat), who is a full sister to grade 1 winner Ops Smile and is the dam of multiple stakes winner and stakes producer Snow Cone (Cryptoclearance) and graded-placed Devotion Unbridled (Unbridled), the dam of Miss Smarty Pants.