This 144th Preakness Stakes has been marked with the lack of participation from Country House or Maximum Security. However, there are still twelve talented horses currently probable for the race. One of these horses is Win Win Win.
It is in Win Win Win’s blood to win the Preakness Stakes. His damsire, Smarty Jones, won the Preakness Stakes in 2004. Furthermore, his grandsire Sunday Silence won the Preakness in 1989. All of Win Win Win’s connections hope that he will be able to carry on this legacy.
Win Win Win was born at Live Oak Stud in Ocala, Florida on March 26, 2016. Win Win Win was the third foal from his dam Miss Smarty Pants. He was, unfortunately, also her last. Miss Smarty Pants passed away in 2017. Win Win Win’s sire, Hat Trick, is a multiple graded stakes winner from Japan.
With so many talented horses in his pedigree, it was no surprise that Live Oak Stud decided to keep this colt. He was revered as one of the top foals from their 2016 crop. After his early education, Live Oak Stud sent their colt to trainer Mike Trombetta. Trombetta too has his experience with the Preakness Stakes. In 2006, he saddled Sweetnorthernsaint for a second-place finish in the Preakness. Win Win Win will be his chance at redemption.
Win Win Win made his first start on the turf-course at Laurel Park in November of 2018, finishing first. He then tried the dirt one month later, winning again. He was then stepped up in class for the Heft Stakes on Dec. 29th, 2018, finishing second behind fellow Preakness Stakes contender Alwaysmining.
Win Win Win returned to his home state of Florida for the winter. There, he matured. He began his three-year old season in the Pasco Stakes, winning by 7 ¼ lengths in a track and stakes record time of 1:20.89 for seven furlongs.
It was now clear to Win Win Win’s connections that they had a real racehorse on their hands. He was ready to be stepped up into graded company. He made his first attempt at a graded stakes victory in the Gr.2 Tampa Bay Derby. He was the favorite but finished third behind Tacitus and Outshine.
The horse’s next attempt in graded company was in the Gr.2 Blue Grass Stakes. Despite being stopped dead in his tracks around the far turn, Win Win Win was able to rally down the center of the track to finish second behind Vekoma.
Win Win Win’s next start would be his biggest test of all: the Kentucky Derby. He broke from post fourteen and race four wide throughout the race. He, however, failed to show the same running ability he did in his previous starts, finishing ninth in a field of nineteen.
Following the Kentucky Derby, Win Win Win returned to trainer Mike Trombetta’s homebase in Maryland. There he has been resting and partaking in light exercise in preparation for the Gr.1 Preakness Stakes.
Win Win Win will have a home state advantage over many of the other horses in the Preakness. The only question is whether or not he can get a better trip than he did in the Derby. If he can, it is likely that we will see the same Win Win Win that we saw in the Tampa Bay Derby and Blue Grass Stakes.
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