Kentucky Derby 2019 Daily: Win Win Win hitting the trail

Kentucky Derby 2019 Daily: Win Win Win hitting the trail
Photo: SV Photography

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.

Win Win Win, track record-breaking hero in last weekend’s Pasco Stakes, will hit the 2019 Kentucky Derby trail in his next start, trainer Michael Trombetta says. Now, he just has to decide in which race.

Following the victory going seven furlongs in 1:20.89, the Florida-bred son of Hat Trick remained in his home state and will re-enter training next week toward a start in either the Feb. 9 Sam F. Davis (G3) or March 9 Tampa Bay Derby (G2).

“I’m probably leaning much more in the direction of the Tampa Bay Derby,” Trombetta said. “They all like a little bit of time when they run hard, and looking at the schedule, it gets a little cramped. You want to do enough, but not too much.”

A Live Oak Plantation homebred, Win Win Win has done almost only that in his four-race career, which kicked off at Laurel Park. He broke his maiden Nov. 3, came back to beat winners Dec. 7 and finished second as he continued to climb the ladder in the Heft Stakes on Dec. 29.

“He got away really poorly from the gate,” Trombetta said, with Win Win Win last of five at the break. “He made a nice run, and the race may be a little better than it appears. The track wasn’t in its best shape that day. It was a little wet and speed-favoring.”

That led to an eye-catching victory once the colt shipped South. Win Win Win broke a step slow in the Pasco as well but raced wide and from off the pace, looking much the best at Tampa Bay downs. The final margin of victory was 7 1/4 lengths.

Overdeliver, a Todd Pletcher-trained debut winner, rain second, with Cave Run, a Godolphin homebred who also won first out, third in the Pasco.

“He certainly broke through to a different level last weekend,” Trombetta said. “What he had done before was great, but this was much, much better.”

Trombetta, who keeps horses in Maryland and Florida, said he trains about a dozen at any time for Live Oak Plantation. He has saddled one previous Kentucky Derby starter, Sweetnorthernsaint, who finished seventh and went on to run second to Bernardini in the Preakness stakes.

“All trainers and owners aspire to be around nice horses,” Trombetta said. “It’s only a select few who ever get that far, so to be able to do it would be fantastic. If the horse warrants going in that direction, there’s nothing better.

“I guess we just have to take it one step at a time and see what he does.”

Gray Attempt to continue on

Smarty Jones Stakes winner Gray Attempt, who won Friday’s prep on the front end, is expected to run back when Oaklawn Park’s road to the Derby continues next month in the Southwest Stakes (G3).

Trainer Jinks Fires and owner Dwight Pruett have been here before. In 2016, their Discreetness also won the Smarty Jones. That horse hasn’t returned to the winner’s circle in 11 starts since then.

Speaking to Ed DeRosa, reporting for, Pruett said Gray Attempt “has a better mind” than his predecessor. 

“He has no bad habits,” Pruett added. “He does what we ask him, and we don’t see speed as a bad habit.”

Trainer Steve Asmussen had three runners in the Smarty Jones’ eight-horse field. While each were defeated, perhaps it’s not the last week see of them on the trail.

“Kind of a merry-go round race,” Asmussen said of Friday’s feature. “They went in :46 and change fractions. That's pretty solid, but nobody changed any positions. First day of the meet, things will change. We'll see what happens.”

The works

Classy John — A back-to-back stakes winner against fellow Louisiana-breds, he could step back into open company for a race like the Risen Star (G2). Dallas Stewart trains and sent him through a bullet half mile in 48 seconds Saturday at Fair Grounds.

Improbable — The unbeaten Bob Baffert trainee’s four breeze of the new year measured five furlongs Saturday in 1:02.00. The next race spot hasn’t been indicated yet.

Instagrand — Ditto the future of Instagrand, whose fifth breeze back from a lengthy layoff marked his first five-furlong drill of his 3-year-old season. Clockers caught him in 1:02.20.

Kingly — We’re awaiting an encore from Mohaymen’s brother, who won Dec. 1 on debut and has worked consistently since then. Saturday’s six-furlong breeze went in 1:15.00.

Knicks Go — One who Win Win Win could run into in Florida, the Breeders’ Cup Juvenile runner-up breezed five furlongs in 58.40 seconds Saturday morning at Tampa Bay Downs. Both his works this year were bullets.

Nolo Contesto — The second out winner for the connections of Accelerate could return in next weekend’s Robert B. Lewis (G3), with Saturday’s work going five furlongs in 1:00.80 at Santa Anita Park.

In case you missed it…

Friday’s Derby Daily report focused on a newcomer to the barn — but not the Derby trail — for trainer Mark Casse, who also discussed recent Lecomte Stakes (G3) winner War of Will.

Horse Racing Nation's Kentucky Derby daily blog counts down to the May 4, 2019, race at Churchill Downs with a once-a-day update on all things Derby. Get the latest news and chatter, workout reports and a look at fields for upcoming preps all in once place.

Top Stories

Pre-entires for the Breeders' Cup were submitted o...
According to a newly disclosed report from the Cal...
There is no event in racing that offers better val...
All 14 Breeders' Cup races carry their own intrigu...
Calling them his “dream team,” trainer Bob Baffert...