Few first-crop stallions kick off their freshman year with a bigger explosion than Win Win Win, who topped the Ocala Breeders’ Sales March 2-year-olds in training sale with a $1.8 million filly out of the Union Rags mare Unanimity. Along the way to her sale-topping price, the filly equaled an OBS record with a quarter-mile breeze in :20.20. A second Win Win Win filly, this one out of the winning Into Mischief mare Genau, sold for a healthy $130,000 after posting a :21 flat quarter-mile. Both fillies were bred by Ocala Stud, which stands their sire.

From the start, there was every reason to believe that Win Win Win would transmit speed. The Live Oak Stud homebred set a Tampa Bay Downs track record of 1:20.89 for seven furlongs while winning the 2019 Pasco Stakes. 

Expanding the resume, he exhibited stamina with a third in the Lambholm South Tampa Bay Derby (G2) and second in the Toyota Blue Grass Stakes (G2). He finished his 3-year-old season with a win in the one-mile Manila Stakes on the turf at Belmont, showcasing versatility.

Win Win Win capstoned his racing career as a 4-year-old conquering the seven furlong Forego Stakes Presented by America’s Best Racing (G1) at Saratoga, running down Grade 1 winner Complexity in the final strides. His other victims that day included champion sprinter Whitmore and Grade 1 winners Firenze Fire, Lexitonian, Mind Control and True Timber. Win Win Win left racing with five wins from 12 starts and earnings of $601,600.

Sired by 2005 Japanese champion sprinter Hat Trick, a son of Sunday Silence who became a champion sire in Brazil, Win Win Win is out of Miss Smarty Pants (by Smarty Jones), a winning half-sister to 2011 Noble Damsel Stakes (G3) winner Unbridled Humor (by Distorted Humor). Miss Smarty Pants, in turn, is out of Grade 3 placed stakes winner Devotion Unbridled (by Unbridled), whose half-sister Snow Cone (by Cryptoclearance) won two stakes races at Calder and produced 2020 Durham Cup Stakes (G3) winner Salute With Honor (by To Honor and Serve). Produced from the stakes-winning Caveat mare Icy Warning, Devotion Unbridled is also a half-sister to Cool Slew (by Seattle Slew), dam of 2007 Grey Breeders’ Cup Stakes (G3) winner Globetrotter (by Street Cry), and Revel in the Win (by Red Bullet), dam of 2013 Bourbon Stakes (G3) winner Poker Player (by Harlan’s Holiday).

“Win Win Win is my kind of horse,” says Ocala Stud’s David O’Farrell. “He’s a powerful horse with a tremendous shoulder and is very smart. He was a versatile racehorse and he’s an outcross to most mares, making him a very exciting young stallion. He’s not going to be a one-shot sire, either. We have a number of other young horses by him that are progressing extremely well and we look forward to seeing them run.” 

Win Win Win is standing the 2024 season for $5,000.

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