Win Win Win: Derby Points 50

Win Win Win is Hat Trick colt trained by Michael Trombetta, ridden by Julian Pimentel and owned by Live Oak Plantation.

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Michael Trombetta had the Kentucky Derby favorite Sweetnorthernsaint in 2006 and finished 7th. Sweetnorthernsaint finished 2nd in the Preakness. Trombetta has yet to strike a win on the Triple Crown trail or in the Breeders’ Cup but does own 10 Graded Stakes wins including the Grade I Nearctic Stakes with Next Question at Woodbine. Trombetta is not a high volume trainer and has done really well with the horses he works with and is currently winning 16% of his starts in 2019 hitting the board nearly 42% of the time.

Julian Pimentel is riding Win Win Win in his Kentucky Derby debut. Julian is 38 years old and is based in Maryland’s Laurel Park. Pimentel owns 7 Graded Stakes wins during his career and rode Win Win Win for his 1st four races. Jose Ortiz got the mount on Win Win Win for the Tampa Bay Derby and the Blue Grass Stakes finishing 3rd & 2nd respectively and now Pimentel is back aboard Win Win Win as Jose Ortiz selected Derby points leader Tacitus.

Live Oak Plantation is a prolific Florida-based operation in Ocala. The group owns several Breeders’ Cup victories but has yet to strike on the Triple Crown trail. Like Oak has won Florida Owner & Breeder of the Year and its best horse to date (my opinion) is World Approval. They’ve also been able to win several Grade I races with Brilliant Speed, High Fly, To Honor and Serve, Zo Impressive and others.

Why I Like Win Win Win/ Why I Don’t Like Win Win Win

First I love the name. It suggests a horse that will keep trying and Win Win Win lives up to his name. Some horses dazzle with their natural ability and others wow onlookers with perseverance and a ‘no quit’ attitude. That’s Win Win Win.

WWW has had his best race results with Julian Pimentel as his rider with 3 first place finishes and a 2nd. But to give Jose Ortiz credit the level of competition really stepped up in the Tampa Bay Derby and Blue Grass Stakes. But the speed figures (Equibase) also tell the story too (90,99,104,113!, 101, 91). The 113 speed figure draws attention and who really cares who he beat in the Pasco Stakes, that’s a number that very few horses can claim coming into this race….. but again it’s the consistency that troubles me.

My Take on Win Win Win

I’m using Win Win Win underneath on my Trifecta and Superfecta betting. I think a great deal of the horse and I really think he’s live to hit the board. Early Vegas action has Win Win Win at about 22-1 and I’d probably value this horse at 12 to 14-1 or so. So there is good value in playing Win Win Win…… I just think his ceiling is Place or Show.

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@UofLSheriff50. Louisville native, University of Louisville Business School Grad c/o 2004. Co-Founder of

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