Late in 2020 a phone call led to a partnership. Jockey Reylu Gutierrez was struggling. In three short years, roaring like a jumbo jet touching down at JFK, he journeyed from hometown Finger Lakes to the New York Racing Association tracks of Aqueduct, Belmont Park, and Saratoga Race Course. People knew him in the Empire State, so he played a home game each post parade.

“I loved having a cheering section,” Gutierrez said with that infectious smile of his. “I never knew who from the 11^th Grade was going to show up.”

Despite winning his first Saratoga race at the famed meet, victories on the tough circuit were nonexistent by November. When losing finds you, sometimes you need what Gutierrez describes as a “reset.” That’s when Jose Santos Jr. rang.

The jockey agent was making moves with an expanding client list, and the pair had much in common ... age, sense of work ethic, and humor, and a willingness to fly standby. Gutierrez was the son of the trainer, while Santos’ father was a celebrated rider. It was a good match.

Traditionally, jockeys stay put during what are called “meets,” and the length can vary from a month (Keeneland) to several (NYRA tracks). Colony members serve as part-support system and part-hostile environment. Everyone is chasing what is called a riding title … a coveted prize which can lead to future opportunities. Rivalries go with the territory, but in this era, there is a fair amount of transience as jockeys come and go on a regular basis, especially when stakes action is carded. Large barns “ship,” competing for purse money in both “non-graded” and “graded” races. These equate to class levels, which are based on what kind of competition a runner is used to facing.

In 2021, Santos wanted Gutierrez to shift his tack (gear) — New York was over for the time being. “Jose is like an older brother, and so he came and got me on Dec 28, and we drove and drove, from New York to Texas,” he said.

The target was Sam Houston Race Park, and afterward Lone Star Park in Grand Prairie. Gutierrez had an aggressive style out of the gate, which continues to be his signature. He rode well, but that bad taste in his mouth from New York lingered. “I was riding with a chip on my shoulder last year,” Gutierrez admitted. “I’m a New Yorker, and I had to leave … that didn’t sit well with me, but I needed to understand that this is a business.”

Santos was the linchpin, and he knew that the college-educated Gutierrez still needed time to mature. The jockey calls it “a mental patience,” which is honed. He took direction from Santos, as the 2021 dates flipped on the calendar. It wasn’t easy. After that Texas swing though, he struck gold in the September-running of the Pocahontas Stakes at Churchill Downs aboard a Bret Calhoun-trained filly named Hidden Connection. That was a Breeders’ Cup “Win and You’re In” race, and Gutierrez earned his first trip to the big event to be held at Del Mar in November. Higher class horses at Churchill Downs followed, and the pair turned their attention to the Fair Grounds, which opened just before December.

New Orleans seemed like a fit, since established barns winter there. Brad Cox, the two-time Eclipse Award-winning trainer, along with Calhoun, Tom Amoss, Al Stall, and a host of other accomplished conditioners compete at Fair Grounds. The plan was to start traditional, with a sprinkling of Oaklawn Park mounts that were generously offered by trainer John Ortiz, but there would be a new component, too. With a travel agent at the ready, it was time to take his game on the road.

Over the course of eight months, no other rider in America would try 18 tracks … and counting. That’s 18 different Jockey’s Rooms, paddocks, surfaces, and winner’s circles.

“I know flight schedules, and every Delta Lounge,” Gutierrez said with a grin. “I could work the desk at the gate running the standby board.” On any given weekend, you can find Gutierrez at 10,000 feet, racking up frequent-flyer miles in the air and furlongs on the track. It’s a challenge though, especially with those deal-breaking cancellations and pesky connection flights. “That’s where the mental patience gets tested,” Gutierrez said calmly, “I don’t always get to a track early so I can go through my pregame routine.”

Gutierrez aboard Hidden Connection (Eclipse Sportswire)

Besides riding in actual races, jockeys also “work” horses for trainers because it can help maintain fitness and it’s a key to relationships. Currently, Gutierrez is located at Ellis Park in Kentucky, but he also rides regularly at Horseshoe Indianapolis and Colonial Downs. A recent weekend blitz saw him at Remington Park on a Friday night in Oklahoma City, up to FanDuel Sportsbook and Racing for the St. Louis Derby on Saturday, and then back at Ellis on Sunday. Exercising a trainer’s horses is equally important, so he rose at 4 a.m. to work a set for Calhoun, Cox, and Randy Morse; thus, pushing back his flight to Oklahoma City.

“Jose reminds me of the balance that I need,” Gutierrez said. “I think that is essential when you are in airports and things don’t go your way.”

Like any business traveler, you have to remain flexible.

Steadily, Reylu Gutierrez’s approach has changed. Opportunities to ride for the likes of Shortleaf Stable and West Point Thoroughbreds arrived. This year, he made appearances in the Pegasus World Cup and along the Kentucky Derby Trail. He rode Hidden Connection in the Longines Kentucky Oaks and Ortiz’s Barber Road in the Kentucky Derby Presented by Woodford Reserve. Professionalism and patience are carry-ons.

“This schedule isn’t for every young jockey, I have learned how to pack over the course of this past year … no extra socks … stay light,” Gutierrez said with a laugh. With some 540-plus starts and counting, the New Yorker has harnessed that sense of failure, to work in his favor. “I am going to build where I am at,” Gutierrez said, “I adjust on the fly, literally.” There is nothing easy when it comes to navigating an airport — early calls, delays, cancellations, connections — sounds just like life around a racetrack.