Win Win Win and trainer Mike Trombetta hope to bring Kentucky Derby glory back to Maryland

Win Win Win runs on the track during morning training for the Kentucky Derby at Churchill Downs on May 1, 2019 in Louisville, Ky.

LOUISVILLE, KY. — Win Win Win did not wait long to make his presence known at Churchill Downs.

The Maryland-based colt was going about his business Sunday morning, charging off for his final timed workout before the Kentucky Derby, when fellow Derby hopefuls Country House and Tacitus suddenly came up on his inside. The three horses ended up almost side by side as they pounded over the dirt, giving spectators a rare pre-Derby thrill.


Win Win Win had largely flown under the radar until that point, but his competitive workout — and the professionalism he and jockey Julian Pimentel showed in handling it — became the talk of the backside.

Was that what his trainer, low-key Perry Hall native Mike Trombetta, wanted?


“Well, it wasn’t my preference,” he said in typically understated fashion. “But no harm done.”

Win Win Win has already taken his Maryland trainer on quite a ride this spring. He had to finish top two in the Blue Grass Stakes on April 6 just to qualify for the Derby, and his prospects didn’t look good after a bumpy start left him well back. But Win Win Win mounted a furious charge, moving up from eighth at the three-quarter pole to snatch the runner-up spot by a nose.

It might not have been the path to Louisville his trainer imagined, but here they are.

As much as the Derby is about the Bob Bafferts and Todd Pletchers of the world, it’s also about horsemen such as Trombetta, who run successful local operations but wait their whole careers for one or two horses gifted enough to take them to Churchill Downs on the first Saturday in May.

“I think most of the people we work beside and compete against in Maryland know how hard it is to get into this thing,” Trombetta said. “So they wish us well.”

If Win Win Win were to triumph Saturday, he’d become the first Maryland-trained horse since Animal Kingdom in 2011 to capture the first jewel of the Triple Crown.

Trombetta, who maintains barns at Fair Hill and Laurel Park, doesn’t want the Derby spectacle to pull him out of his cherished routines. But he’s also not looking to throw water on the magnitude of the race.

“It means everything,” said his wife of 31 years, Marie. “It’s the top of the line in the horse world. There are other races worth more money, but it’s not about that. You say you’re in the Kentucky Derby and that’s the pinnacle.”


She joked that her husband deals with the stress by throwing himself into daily chores; you’ll never find tidier stalls than his. Meanwhile, the couple planned to fly back to Baltimore on Wednesday evening to collect their school-aged sons, Michael Jr. and Dominic. Daughter Nicole will join them in Louisville on Thursday.

The 52-year-old Trombetta fell in love with the game as a teenager, tagging along to the track with his father, Rudy, and mucking out stalls for longtime Maryland trainer Frank Hendricks before he started his school days at Perry Hall High.

He last brought a horse to the Derby in 2006. Sweetnorthernsaint ended up the post-time favorite that year, and Trombetta will never forget the crush of cameras and microphones that followed him around the barns.

“I knew it was going to be kind of like this,” he said at the time. “But I didn’t think I’d need sheriffs to keep people away from [Sweetnorthernsaint].”

After his horse finished seventh, Trombetta said that going in as the betting favorite “really messed me up.” But with 13 years of perspective, he carries no regrets about his previous trip to the Derby.

Sweetnorthernsaint’s success (he’d go on to finish second in a Preakness overshadowed by Barbaro’s breakdown) allowed Trombetta to make the final leap into full-time training. He’d worked for his brother’s construction company until then.


“It was coming,” he said of his stable’s progress. ”But that was the one that gave it the big push.”

Laurel-based Pimentel brings his own underdog story to the mix. He rode Win Win Win to three victories in his first four career races, including a track-record performance in the seven-furlong Pasco Stakes at Tampa Bay Downs. But when Win Win Win started looking like a serious Derby contender, Trombetta replaced the 38-year-old Colombian with Irad Ortiz Jr., the leading money winner in North America last year.

With Ortiz aboard, Win Win Win finished third in the Tampa Bay Derby and second in the Blue Grass. But Ortiz opted to ride Baffert-trained Improbable in the Derby, and Trombetta turned right back to Pimentel.

Though Pimentel is generally one of top 10 riders at Laurel Park, he rarely gets to perform on the national stage. He certainly earned the respect of Hall of Fame trainer Bill Mott, whose two horses hooked up with Win Win Win in that unexpected workout last Sunday.

“What a good kid, level-headed, very patient,” Mott told reporters afterward. “He was as courteous on the racetrack as he is when he’s on his feet. I’m thrilled to death to see him have an opportunity to ride the Derby.”

Win Win Win is not one of the favorites for Saturday’s race. But Churchill Downs handicapper Mike Battaglia listed him as a live 15-1 choice in the morning line, indicating the respect Trombetta’s horse has earned with his workouts.


The trainers at Live Oak Plantation in Ocala, Fla., always saw promise in the big, dark bay colt before they sent him to Trombetta as a 2-year-old. They just thought that potential might manifest on turf instead of dirt.

“He was always a big, strong colt and athletic for his size. We noticed that early,” said Joe Ambrosia, who manages Live Oak’s training division for owner Charlotte Weber. “He kind of got over the ground here, like we thought he would be a turf horse; his pedigree leans to that. But thankfully he’s not, because you would not be calling me up if he was in a turf race.”

Ambrosia credited Trombetta, who has received horses from Live Oak for almost a decade, with finding the best in Win Win Win. “Mike is excellent at bringing horses along,” he said. “That’s one of the reasons he received this horse. He’s a little more hands on … because he runs a smaller operation than some of the big guys out there that have 100 or 200 horses. He really maximizes their ability.”

Trombetta said Win Win Win started separating himself from his 2-year-old stablemates last fall, when he consistently breezed well and picked up two victories at Laurel Park. Thoughts of the Derby blossomed after the colt’s record-setting performance at Tampa Bay Downs on Jan. 19.

Though Live Oak has pumped out excellent thoroughbreds for decades, Ambrosia said there’s nothing like the Derby for bringing attention to the entire operation. That’s part of the reason he wanted to switch off his television in despair after watching Win Win Win break flat-footed in the Blue Grass.

“You kind of see everything go out the window, like there’s no chance,” Ambrosia recalled.


But the colt mustered the same athleticism that impressed his handlers early on to pull off that clutch second-place finish. Because he has yet to triumph going around two turns, skeptics wonder if Win Win Win will handle the 1¼-mile distance in the Derby.

“It’s a bit of a new dynamic for all of us,” Trombetta said. “But all we can do is take them there and see how they’re going to do.”