The King Cheek
The King Cheek and jockey Jaime Rodriguez won the Sir Barton Stakes. Photo by Cynthia Longo.

It was early in the 2020 Delaware Park meet, and agent John Weilbacher needed a jockey to represent. His main Delaware client had let him go, and it was shaping up to be a long, dry summer.

“I was a little rattled,” he admitted.

And then his phone started ringing. The trainer Victor Carrasco. Jockey Guillermo Rodriguez. An assistant trainer. Another rider or two.

“Probably five or six people that knew him said, ‘Hey, man, this kid can really ride. You should take his book,’” Weilbacher recalled.

“This kid,” the now-30-year-old Jaime Rodriguez, was coming off a dominant 2019 season at Finger Lakes. He’d earned leading rider honors while winning 146 races – 40 more than any other pilot at that track. His $2.1 million in earnings that year also were tops.

Now he was looking to come to the Mid-Atlantic. With the Covid-19 pandemic in full swing, Finger Lakes, his longtime home, had delayed its opening, from late April to, ultimately, July 20, and Rodriguez had run out of patience.

“I told my girlfriend, ‘You know what, babe? We gotta go,’” Rodriguez recalled. “’I’m young. You’re young. We got two kids.’”

He continued, “I’m really happy; I do awesome at Finger Lakes. But I want to move on, you know. I want to do better. I don’t want to be [racing] in a little track my whole life.”

Given the tip, Weilbacher reviewed the jockey’s record. He watched races. And he made phone calls, “just to kind of get what kind of guy he is.”

What did he hear?

“Everybody said his work ethic is unbelievable,” Weilbacher said. “And, you know, that he’s a really, really good rider.”

The new team did well during the 2020 Delaware meet. Rodriguez won 56 races, tied for third most at the track, and his $1.3 million in earnings were also third highest. In all, the rider visited the winner’s circle 107 times in ’20.

But that seems to have been nothing more than a prelude to what he’s doing this year. Riding first call at Delaware for leading trainer Jamie Ness, Rodriguez won two races on opening day, May 26, and followed that up with five wins on the second day of the meet.

He hasn’t looked back. Through June 17, Rodriguez has 18 wins from 61 starters. No other jockey – not even six-time leading rider Carol Cedeno – has won more than eight races.

“If I got a closer, if I got a front-runner, a turf horse, it really doesn’t matter,” Ness said. “He’s not a one-dimensional rider. I just think he does everything right.”

That versatility was on full display when Rodriguez rode the Ness-trained The King Cheek to a win in the $100,000 Sir Barton Stakes on the Preakness undercard at Pimlico. The King Cheek popped the latches on top and controlled the race through moderate early fractions. But odds-on favorite Hozier cruised up and went by, opening a nearly-one-length lead.

Challenged, Rodriguez and The King Cheek fought back, drew even, and won the race by a head.

“That was an experience,” Rodriguez said. “To win with a horse on Preakness day, that was amazing.”

It’s been quite a journey for Rodriguez, who grew up in Carolina, Puerto Rico. As young as 10, he started thinking the jockey’s life was for him.

“My mom’s cousin, Wilfredo Rohena, is a jockey at Finger Lakes [he’s one of four Rohenas to ride there in recent years],” Rodriguez said. “And I saw him and I said, ‘Man, I want to be a jockey.’”

Rohena helped Rodriguez get into the island’s famous Escuela Vocacional Hipica jockey school, which has produced such riding luminaries as John Velazquez, the Ortiz brothers Irad and Jose, and last year’s apprentice Eclipse award winner Alexander Crispin.

In preparation for the school, Rodriguez took to the streets – literally.

“I had a little horse at the house,” he said. “They gave me a little saddle, and I was galloping in the street, and they told me, ‘Be careful, you’re going to get hurt.’”

Given the admonition, Rodriguez and his horse went instead to the local baseball park.

“I went down and I was doing it every day. Every day,” he recalled. “No vest, no helmet, nothing.”

Jaime Rodriguez won five races at Delaware Park May 29. Photo by

After two years at the school, he began riding races in Puerto Rico in 2010, before relocating to the NYRA tracks in New York later that same year. Many other stops have followed, and along the way, he connected with Amber Cobb, his girlfriend and the mother of their two children, seven-year-old daughter Addilyn and two-year-old son Liam.

“For those two kids, I’d do anything,” Rodriguez said.

Cobb, a trainer currently stabled at Delaware, has nearly 20 horses in training, Rodriguez said. In addition to galloping in the mornings and riding in the afternoons, Rodriguez lends a hand around the barn, too, serving as groom, hotwalker, or whatever else needs doing.

“Everything, from his work ethic in the morning to his effort on the track” is what’s powering the success Rodriguez is enjoying, Ness said. “He’s a real up-and-coming rider.”

Rodriguez likes the sound of that. He remembers fondly his first stakes win, which came aboard 31-1 shot Goldzar in the 2011 Ecclesiastic Stakes on closing day of that year’s Saratoga meet. And he’s hoping more appearances in big races on big days are still to come.

“I want to try my talent in different environments,” Rodriguez said. “See how good I can go. I want to fly high and be proud, you know?”