Back in the Saddle: Pimentel gets another chance on Win Win Win

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In 2011, Julian Pimentel won a maiden race aboard a 2-year-old first-time starter for trainer Michael Matz at Delaware Park. The jockey was impressed, but also disappointed and realistic.

“We will never ride this horse again,” he told his agent Ronnie Gerardo. “This is a freak.”

Gerardo was aghast. Racing is a business, but this was Delaware Park, Matz, a maiden race. Surely, the agent could get his jockey a return call. He went to the barn, talked to Matz, did all the right things. But Pimentel was correct. He never rode the horse – eventual Belmont Stakes winner and $1.8 million earner Union Rags – again.

In January, Pimentel went to Tampa Bay Downs to ride Win Win Win in the Pasco Stakes for trainer Mike Trombetta and they set the track record while winning by 7 1/4 lengths. Afterward, the jockey gave his agent an ominous report.

“We might not ride this horse back.”

Again, he was right. With eyes on a spot in the Kentucky Derby field, Trombetta and Live Oak Plantation went with big-race experience and tapped Eclipse Award winner Irad Ortiz Jr. for the mount in the Tampa Bay Derby in March.

“I was like, ‘Wow,’ but I understand. It’s a business,” said Gerardo, a former jockey. “People want the top rider in the country. What can you do? Business is business.”

Pimentel echoed the sentiments, but probably kicked a trash can somewhere just the same.

“I understand, I’ve been in the business a long time,” said Pimentel 3-for-4 with a second on the horse. “They wanted somebody who had already ridden the race. That’s the way it works. Of course I was disappointed. But it is what it is.”

Ortiz and Win Win Win finished third in the Tampa Bay Derby, and a troubled second in the Blue Grass at Keeneland. The finishes were good enough to qualify for the Kentucky Derby, but also not quite good enough to keep Ortiz. The national leader in wins and earnings last year chose Improbable from the powerful stable of trainer Bob Baffert – leaving Win Win Win in need of a jockey.

And this time, Pimentel was wrong. Trombetta talked it over with owner/breeder Charlotte Weber and her team, and came back to the only jockey to win on the Florida-bred son of Hat Trick. Trombetta called Pimentel first.

“He caught me by surprise,” the jockey said. “He asked if I had any plans for Kentucky Derby Day. It was pretty neat.”

Pimentel immediately called Gerardo, his agent for 11 years.

“Hey,” the jockey said. “Trombetta called me and we’re back on Win Win Win.”

“Yeah, right,” replied a skeptical Gerardo, who couldn’t be convinced of the good news. He hung up and went to the source, at first via text.

“Mike, question: Julian called me and he said something about Win Win Win and the Derby.”

Sensing an opportunity, Trombetta responded with a phone call.

“Julian drinking early this morning?” he said. “I don’t know what you’re talking about.”

“Stop messing with me,” Gerardo answered.

And finally, Trombetta told the truth.

“Listen, you’re on speaker phone and my wife and my son are in the truck. Don’t start screaming or anything. Ortiz is taking off. We talked to the owners and they said they wanted Julian to ride the horse again.”

Of course, Gerardo went a little nuts.

“I started screaming,” he said. “It was a very exciting call to get.”

It took six weeks or so, but Pimentel and Gerardo went from the bottom to the top in one phone call. Well, two phone calls, a text and one short-lived joke. They’re proud, appreciative and they get it – still.

“It was a business decision and now look how it goes,” Gerardo said of the move to Ortiz and back. “If we didn’t accept it so well then, maybe we wouldn’t be back on the horse now. Maybe if we rode him in the Tampa Bay Derby and something happened Julian would never get back on the horse. We’re a team with Mike. He supports us. We’re behind him.”

And now they’re going to work. Gerardo was booking flights, hotels, other details, even a few other mounts for Derby Week at Churchill Downs. The Maryland-based Pimentel, 28, was studying video replays of Win Win Win, other 2019 contenders and past runnings of the Derby. One the one hand, it’s another horse race. On the other, it’s the chance of a lifetime.

“The Derby? That’s everybody’s dream,” said Pimentel, a native of Colombia who rode his first North American race in 2000. “Even before I rode I used to joke around about being in the Derby someday. It’s the biggest race for us, even though it might not be the biggest money. Everybody asks you about it when they hear you are a jockey. ‘You’re a jockey? You ever ride in the Derby?’ ”

All being well, Pimentel will be able to say yes come May 4. He rode the great Ben’s Cat multiple times, won the Grade 3 General George on Imperial Hint in 2017, had that one spin on Union Rags. He’s ridden more than 10,000 races, and won more than 1,600. But this is different. 

“We’re throwing everything on the table,” he said. “I’ll ask the guys who have been in it, I’ll get advice, I’ll watch video and try to have a plan. You want to have an idea of what’s going to happen, but when the gates open it’s still a race and there are 20 horses. How do you know what’s going to happen?”

Most importantly, the jockey believes in Win Win Win, a horse he teamed up with early during Saturday workout sessions at Fair Hill Training Center.

“He was one of my favoirtes,” Pimentel said of first impressions last year. “You don’t know until they run, but he always worked good. He knows what he’s doing. He’s got some attitude too. One time I went to work him in the morning and he tried to jump up on the pony.”

Pimentel thinks the dark bay colt possesses enough speed, and more tactical ability than maybe he showed in the Tampa Derby or the Blue Grass. He’s improving, learning, changing. Trombetta called it “evolving.” All that is good enough for Pimentel, who has never ridden at Churchill Downs.

“He’s a seriously nice horse,” Pimentel said. “When he won going seven-eighths at Tampa, the question was always if he could run longer. Now it looks like he can run all day. He has done everything right even though he hasn’t won again. He’s been running at the end. That shows that he’s a nice horse. At Keeneland, you check a horse like that and sometimes they don’t come back. They give up. It’s nobody’s fault, it happens. But he came back.”

Yes he did.

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Hey, Julian Pimtentel, what kind of trip would win the Derby?
“A good trip, whatever that is. The last couple of years it’s been speed favoring. You see horses go :22, :46 and they win. How can they do that? Then you saw Orb coming from the back and Mine That Bird was a hundred lengths behind and he won. You don’t know what it’s going to be like. I don’t think you’re ever going to get a slow pace in the Derby. Pace will help this horse, but he doesn’t have to be too far back to do well.”

Hey, Ronnie Gerardo, what would it be like for your jockey Julian Pimentel to win the Kentucky Derby?
“That would be . . . I can’t even tell you. I won’t be sleeping that night. It’s a dream, to get lucky enough to get one horse to go there. At first we thought our ticket got taken away. There would be a lot of emotions.”