Kentucky Derby 2019 Daily: Win Win Win inspiring confidence

Welcome to Horse Racing Nation’s Kentucky Derby Daily, which will each day leading up to the May 4 race at Churchill Downs detail all the news and notes related to contenders in one convenient space.

Kentucky Derby 2019 contender Win Win Win will ship mid-week to Churchill Downs ahead of a final Sunday breeze, said Michael Trombetta, who has finalized plans for the closing Blue Grass Stakes (G2) runner-up., according to trainer Michael Trombetta.

A son of Japanese-bred Hat Trick, Win Win Win, who also ran third in the Tampa Bay Derby (G2), worked last Sunday over Maryland's Fair Hill Training Center synthetic surface, going the five furlongs in 1:01.00. He galloped out a six furlong in 1:13.00 in company with stablemate Two Swords.

“It’s worked well for him in the past,” Trombetta said of his choice to use the synthetic. “He trains on the dirt as well, but this weekend I chose to train him on the synthetic, just for the reason that we got quite a bit of rain over the weekend. The (dirt) tracks were actually good, but I thought he would get a lot more out of the synthetic work.

Trombetta has made the right choices for the career $367,300 earner in the past, including a decision to forego on the Wood Memorial (G2) in favor of Keeneland.

“I didn’t have the best of luck shipping up to Aqueduct this winter and I thought it was a pretty big disadvantage to ship into the track and run,” the trainer said. “I was going to have to ship one way or the other, and I just thought that, of the two surfaces, Keeneland would be more accustomed to what he would like.”

Absorbing a bump right out of the gate, Win Win Win was able to rally to hit the wire second by a nose over Signalman in the Blue Grass under jockey Irad Ortiz Jr., who decided to take the mount on Improbable in the Kentucky Derby.

“Irad chose to ride elsewhere,” Trombetta said. “He was offered a pretty nice horse here, but he decided to go that route.”

Julian Pimentel will pick up the mount on the Live Oak Plantation runner.  

Pimentel piloted Win Win Win in four starts, winning three of them, including the record-breaking Pasco Stakes victory in which the colt went seven furlongs in 1:20.89 on Jan. 19 at Tampa Bay Downs.

Having proven himself around two turns, Win Win Win will head to the Kentucky Derby a well-regarded closer for Trombetta, who will stable his second runner in the race following Sweetnorthernsaint's seventh-place finish in 2006.

“One of the interesting dynamics of this whole thing is that they have to keep graduating, both in company and distances," Trombetta said. "The company gets tougher and the distances get further. That is what separates a lot of them out from the rest of the group.