Pimentel, Doyle to Ride in First Kentucky Derby, Oaks

Jockey Julian Pimentel was in the middle of dinner when the call from Michael Trombetta came asking what he would be doing Kentucky Derby Day.

Pimentel had not ridden Trombetta-trained Win Win Win in the colt's previous two starts, but that call informed him he had the mount back for his first ride in the Kentucky Derby Presented by Woodford Reserve (G1) May 4. He couldn't believe it.

As for jockey Sophie Doyle, she knew she was heading to her first Longines Kentucky Oaks (G1) May 3 when Street Band pulled 3 3/4 lengths clear in the Twinspires.com Fair Grounds Oaks (G2) March 23. She says she was probably cheering louder for herself and Street Band than anyone else in the crowd as they crossed the Fair Grounds Race Course & Slots wire. She now hopes to become the second female jockey to win the Oaks.

Both Pimentel and Doyle were introduced to horse racing through their families, and from a young age, being on the back of a racehorse was the goal. This weekend they'll perform at the highest level at Churchill Downs.

Pimentel, 38, grew up in his native Colombia and visited the racetrack with his uncles, one of whom was a trainer and the other a jockey. Being around the horses, he made up his mind early that he too wanted to become a jockey.

"That's all I ever wanted to be," Pimentel said, "ever since they took me to the racetrack."

While the Kentucky Derby might be a new stage in Pimentel's career, he is no stranger to the spotlight in the mid-Atlantic. Pimentel was aboard four-time Maryland-bred horse of the year Ben's Cat more than any other jockey, riding the veteran gelding in 41 of his 63 starts. He guided Ben's Cat to one of two Turf Monster Handicap (G3T) wins and two of three Parx Dash Handicap (G3T) victories. Under Pimentel, Ben's Cat collected $1,839,545 of his $2,643,782 earnings.

"That was very exciting," Pimentel said. "He was a really, really nice horse, and I'm thankful to be part (of it)."

The spotlight now shifts to Louisville, Ky., where Pimentel will break from post 14 aboard Win Win Win Saturday. Their morning-line odds are 12-1.

Pimentel was aboard Live Oak Plantation's homebred in his first four starts. The Florida-bred Hat Trick colt won his first two races sprinting at Laurel Park, including a 6 1/2-length romp in allowance optional claiming. Win Win Win closed his juvenile season when he rallied to second behind Alwaysmining in the Heft Stakes but really drew attention in his 3-year-old debut.

Trombetta sent Win Win Win to Tampa Bay Downs for the Jan. 19 Pasco Stakes at seven furlongs. Pimentel was in the irons as the colt overcame a slow start and cruised home to a 7 1/4-length win in a track-record time of 1:20.89.

For Win Win Win's first two races around two turns, reigning Eclipse Award winner Irad Ortiz Jr. was assigned the mount. A third-place finish in the Lambholm South Tampa Bay Derby (G2) and a runner-up finish in the Toyota Blue Grass Stakes (G2) at Keeneland gave Win Win Win 50 points on the Road to the Kentucky Derby, enough to place him 16th on the leaderboard, but Ortiz chose to ride Improbable in the Derby.

Trombetta said Live Oak Plantation's Charlotte Weber was adamant Pimentel be the one to ride Win Win Win in the Derby. The trainer said Pimentel's familiarity with the horse adds a comfort level as they head into Saturday.

"It's a whole lot of firsts. It's the first time (going a) mile and a quarter. It's the first time (at the) racetrack. First-time (Derby) jockey on him, too," Trombetta said. "It just keeps adding to it, so this does make me feel so much better."

Pimentel got a taste of the Derby April 28 when he flew in from Maryland to work Win Win Win at Churchill Downs. While Trombetta brought Live Oak Plantation's Souper Courage along as a workmate, Win Win Win found company in Bill Mott's Derby contenders Tacitus and Country House. He ranged up on the outside of them before completing his half-mile work in :47 3/5.

"That was crazy," Pimentel said. "I think if we had planned it, it never would have worked out that way. It happens. We were in the middle of our work, so nothing you can do about that."

Despite the unplanned circumstances, Pimentel said Win Win Win went through the work with ease, giving him confidence for the weekend.

"It's every jockey's dream to be in the Derby," he said. "When you're growing up, when you become a jockey, that's your main goal."

Doyle, 32, was born in England where her mom, Jacqueline Doyle, trained racehorses. Doyle said her mom wanted her to become an eventing rider, but Doyle was smitten with the barn full of Thoroughbred racehorses she was able to ride. She raced in England for seven years and in 2010 was the top woman apprentice. She traveled to Dubai twice to race and, after a few working holidays in the United States, decided to move to America in late 2013 to continue her career.

She credits trainers Kellyn Gorder and John Ortiz, a former assistant for Gorder who went on his own in 2016, for helping her get started. She rode for Gorder while Ortiz helped her shift to the American style of riding from the European style. Doyle first went to California where she knew people but made her way east to Oaklawn Park and, later, Turfway Park and Keeneland. A fixture in Kentucky, Churchill Downs is where she landed her first stateside win in November 2014 aboard the gelding Jaz N Tap for trainer Larry Demeritte.

Friday she will attempt to follow in Rosie Napravnik's footsteps as she rides against the boys in the Oaks. Napravnik won the 2012 Oaks aboard Believe You Can for trainer Larry Jones, who also trains his homebred Street Band, and the 2014 edition with Untapable for Steve Asmussen.

Jones also trained the respective 2008 and 2015 Oaks winners, Proud Spell and Lovely Maria. 

"To think that if I could win it I could be the second female rider to win it would be absolutely amazing," Doyle said. "It's big shoes to fill, but at least I've got a great team that's been there and done it three times already, so I've got 100 percent behind me."

Doyle has been aboard Street Band for the filly's last five of eight starts. The daughter of Istan also campaigned by Jones' wife Cindy, Ray Francis, Medallion Racing, and MyRacehorse.com broke her maiden second time out by 7 1/4 lengths at Ellis Park over the summer and made her second trip to the winner's circle in her sophomore debut at Fair Grounds Race Course & Slots. From that optional-claiming allowance performance, she ran fourth in the Rachel Alexandra Stakes (G2) and broke through in the Fair Grounds Oaks.

Street Band last worked five furlongs April 28 at Churchill Downs and was timed in 1:00 1/5. She will break from post 12 and is listed at 15-1 on the morning line.

"What I like about Street Band is she's feisty. She's like your typical little redhead that can be nice and quiet and you can think, 'Oh, she wouldn't do anything wrong,' and then she'll have like this little explosion go on. You never know what you're going to get out of her," Doyle said. "One minute she can be nice and quiet, the next thing she's on her toes.

"We just have a good connection together. When I'm on her, I'll whistle to her quite a lot, and she knows that's me and a cue to kind of calm down a little bit. The nice thing is, when we're together by ourselves in the race, I guess we have a great connection and rapport with one another that we trust each other. Street Band, when she's under you in a race, it's pretty electric.

"She's got a lot of gears to go through, and she travels so well for you that when you pick up down the stretch, she really battles hard for you. She'll eyeball another horse, and then she'll dig back in and pull away from them."

Doyle's top mounts in the U.S. fall in the filly and mare category. Her first graded stakes win was in the 2015 Thoroughbred Club of America Stakes (G2) with Fioretti, who pulled off a 17-1 upset.

"I guess I must just have a really good connection with them," Doyle said. "I love riding the colts—there's nothing greater than getting on a big, nice, strong colt and feeling the power under you—but the fillies have got it, too. I've just always seemed to have a way with fillies that they tend to run. Looking at my stats, the top end of the higher career horses have all been fillies, so I guess maybe they like me enough."

And she'll look to continue that trend Friday as she chases the lilies on Street Band.