After Race 10 on Fair Grounds Race Course & Slots‘ closing day card March 26, officials presented the trophy for leading rider to jockey Reylu Gutierrez. Just off his horse, red helmet, black silks smattered with dirt, he stood next to his agent Jose Santos Jr. in the winner’s circle to receive the honor.
Santos, dressed sharp in a sports coat and sporting sunglasses above his signature mustache, looked at Gutierrez and said “It means a lot. I see a lot of me in him and I’m sure he sees a lot of him in me. We’re real close friends. We’re like brothers.”
More than just jockey and agent, these two have built a dynamic bond over long drives between the mid-size cities of ‘horse track America,’ teaming up at a low moment in Gutierrez’s young career, and both in their own way being forward thinkers. Gutierrez is known to put his horse into the race, early to the front and successful to the wire. Santos has built a new model for being a jockey agent, offering his riders a well-researched vision for their success, and finding jockeys who are willing and able to market themselves.
Timing is everything in horse racing; when to settle back, when to open up into a full run. When to ask a trainer for a mount on their horse; when to try to ride at one of the sport’s top tracks. When to make a move to pass; when to wait for another opportunity further up the stretch. This is a story of a rider who shot out to the lead only to be shuffled back, and an agent who began at the age of 16 but almost gave up in his early 20s.
Neither Gutierrez’s nor Santos’ timing has always been exactly right, but each of their stories demonstrates resilience and a willingness to move forward. These two have gathered a signature momentum since joining forces, but to guess where it might carry them, we must know the story of how it all began.
Slow to Connect
On the track, and in life, recognizing a true opportunity is no easy task. What might be a lane that opens up to the winner’s circle could actually be a mirage that collapses and results in a troubled trip. The window of opportunity was closing for the talented young jockey Gutierrez, but a bold move on Dec. 29, 2020, to follow Santos’s vision brought him out of a potentially career-defining slump.
At first, Santos didn’t take Gutierrez’s call.
“When I was a bug boy in 2017 I reached out to Jose,” Gutierrez said. “I had only rode in a couple of races at Finger Lakes. I really wanted him to be my agent. I sent him a message on Facebook and he left me unread, didn’t answer it.”
On Oct. 4, 2017, at Finger Lakes, Gutierrez had climbed aboard a horse named Party On in his first race. This was his hometown track where his dad trained and his uncle rode. Gutierrez finished fifth. Eighteen races later on Nov. 2 Gutierrez had his first winner aboard Occhio Della Tigre , who lived up to his “eye of the tiger” name. The front-runner trained by Luis Gutierrez would see father and son team up for the son’s first win. It would be Gutierrez’s only win of the meet.
Gutierrez, like his agent, grew up in a racing family
“He was a bug boy at Finger Lakes, just getting going and he reached out to me right before he went down to Gulfstream,” Santos said. “I was in a weird spot where I was about to get out of being an agent. It just wasn’t going that well at the time, so when he reached out to me I didn’t reply to him.”
Gutierrez moved his tack to Gulfstream Park, and sure enough, he met Santos.
“Our first encounter was because I had fallen,” Gutierrez said. “Jose’s mom actually helped me, took me to a specialist and everything. She didn’t even know me, but she went out of her way to make sure I was all right.”
Gutierrez, the son of a longtime trainer, would seem to have some common ground with Santos, the son of Hall of Fame jockey Jose Santos, who won more than 4,000 races including the 2003 Kentucky Derby (G1) and Preakness Stakes (G1) aboard Funny Cide . Both young, both sons of horsemen—surely when they met, they clicked, end of story.
“Jose told me, ‘I can’t really do anything for you,'” Gutierrez said. “I didn’t believe that, but I was like, ‘All right.'”
Agent Santos
At age 28, Santos was in his tenth year as a fulltime jockey agent. Though he started at the age of 16, he took some time off to go to college, and in his early 20s, when Gutierrez was reaching out to him, he was on looking at other career options.
“I just didn’t have any riders,” Santos said. “I was young in Kentucky trying to make it and going to school all at the same time. I think I just wasn’t taken seriously yet by others. I was going down to Florida because my mom got me a job and she was helping to support me at the time, and she was like ‘I tried to help you follow your dream but at a certain point we’ve got to get realistic about things,’ and I accepted that at the time. I was pretty much a month away from giving up and moving home during the Christmas break when I got a phone call from a guy named David Cabrera, who I had never heard of.”
Santos was on the verge of his breakthrough.
“I had worked a lot with J.R. Caldwell (trainer) in Oklahoma when I was there, so I called him for advice,” Santos said. “When I told him Cabrera had called, he said, ‘Hang up right now and call him back and tell him that you’ll do it.’ So I did. Then I had to call up my mom and explain to her what I just did. She was angry. That was really the beginning of it all. Without that opportunity from David I don’t know what would have happened. That’s what you need in life, those breaks.”
Santos and Cabrera teamed in 2018, and they immediately began having success and winning titles. Currently Santos represents eight jockeys at various tracks. The typical agent represents two. His model does not rely on relationships, but instead Santos offers value to trainer and jockey alike through tireless research into the horses and the condition book. He anticipates where horses will run and he understands which horses have a real shot to win.
“What I try to do is be prepared as possible, to know as many horses as I can possibly know, and which races they are going to go into,” Santos said. “I feel like a lot of what I see from other agents is they try to work off of relationships, and I do try to do that, but more so I just try to have more information because I feel like trainers have gotten on to that I am an information junkie. I feel like they want to do business with me because they know first off if I am asking about a horse, I’ve done the research to know that horse is going to be live in that race. Also, they might want to know who they are running against. They know I have a good idea of what their chances are and the make-up of the field.”
In total, Santos’s jockeys have won six leading rider titles. He represented Declan Carroll when he had a mount in the 2020 Breeders’ Cup, as well as Miguel Mena who had both a mount in the 2019 Breeders’ Cup and the 2020 Kentucky Derby before passing away in 2021.
“I’m a New Yorker. I’m not going to Texas.”
Meanwhile Gutierrez was getting it done without him. From April-September 2018 at Gulfstream, Gutierrez lit it up. He had 58 wins, securing the Gulfstream apprentice title.
At the 2019 winter meet at Aqueduct, Gutierrez went 46-for-334, finishing fifth in the win standings behind star jockeys Manny Franco, Junior Alvarado, Dylan Davis, and Jose Lezcano. With another apprentice title to his name, he was a finalist for a 2019 Eclipse Award as outstanding apprentice jockey.
Reylu Gutierrez, aboard Do Share, celebrates winning the 2019 Tom Fool Handicap (G3) at Aqueduct
Gutierrez has always dreamed he could ride at the top level against the best riders and in the biggest stakes. That dream, and being a kid from Finger Lakes in Farmington, N.Y., sent him to nearby Saratoga Race Course in 2020 to face a jockey colony of Eclipse Champions. It didn’t go well.
“Covid hit,” Gutierrez said. “I hadn’t ridden in a couple months and I didn’t know what to do. All of a sudden I found myself at Saratoga and I went 1 for 84, and that was the first time Jose called me and said ‘You want to come this way, you gotta get out of there,’ but at that moment I was a bit naive.”
Gutierrez moved his tack back to his hometown track. Back in Finger Lakes, he bought a house and began finding peace with the idea that he had his shot, had done well, but maybe he had gone as far as he could go. Did he make his move too soon? Would he get another opportunity?
If asked two years ago in the midst of an epic slump whether he would be in New Orleans, let alone the leading rider, there’s no way Gutierrez could have seen it coming.
“I came back home and decided I needed to restart my career because I needed to learn how to race-ride again,” Gutierrez said. “Saratoga showed me that I don’t know a thing. I was just chilling, galloped some, I was all good. I had just bought a house. Finger Lakes is my home and I thought I was all set.”
However, at this low point, a window of opportunity opened. Gutierrez needed to be bold but he was hesitating. Unsure. Santos offered him a vision, a plan; but now Gutierrez kept saying no.
“(Saratoga) crushed me,” Gutierrez said. “Whenever I ride in New York, whether it’s people who know me from college, people who know me from home, from when I was a groom, a hot walker; they’re there and cheering me on. For people to see you struggle like that, it was embarrassing, it’s very humbling. I got caught thinking ‘What’s wrong with me? I thought I was OK at this, but I guess I’m just nothing.'”
Jose Santos thought otherwise.
“I thought it was just situational,” Santos said. “Saratoga is extremely tough. Once you get in a slump like that and don’t start off right, you’re not going to get in with the right horses. I wanted to work with Rey because I saw a lot of raw talent and a really good person, a driven person. I think anyone who hangs around Rey can see someone who wants it, someone who wants to win. I just knew he had to figure it all out. We’re both young and I’ve been in the same boat. I’ve wanted it bad many times in my life, you just have to figure it all out.”
Santos had been reaching out to Gutierrez over social media to see if he could represent him. He had a vision, but that vision included riding in Texas, and the boy from New York couldn’t quite wrap his head around it.
“Jose was like ‘That’s it for you? You’re better than that. Come to Texas,'” Gutierrez said. “I was like ‘Texas? No, I’m a New Yorker. I’m not going to Texas.'”
At the beginning of December 2020, Gutierrez found his way as far west as Turfway Park in Florence, Ky. Winless in 36 races, it could not have gone any worse.
“We were going back and forth for six months before it really happened,” Santos said. “That’s what he was saying, ‘I want to stay in New York,’ so when he showed up at Turfway I thought ‘OK, he’s willing to leave New York.’ I had him set up to ride with a trainer named Austin Gustafson who wins a lot of races in Texas and we do a lot of work together. That was my sell, ‘Come down here, ride his horses, and let’s build some business. I know that’s not what your goal is but I’ve always thought Texas racing is a good funnel into Kentucky.’
“He was at a point to do either that or go back home to Finger Lakes and he decided to take one more chance.”
Staring down all the doubts and all the losses, Gutierrez made his bold move.
“December 29, (2020), I packed up my car and left Finger Lakes,” Gutierrez said. “I drove 18 hours, met Jose at Oaklawn, stayed the night and then we drove to Houston together.”
Gutierrez began to rally. In 2021 at Sam Houston Race Park, he finished fifth in the jockey standings with 31 wins. Next up in the “Texas plan” was Lone Star Park. Winning with 23% of his mounts, Gutierrez finished in the top three. From the back of the pack toward the front, Gutierrez and Santos were knocking on the door of a riding title. But with the Texas meets in the rearview mirror, where next?
Reylu’s Rally
Enter trainer Bret Calhoun. In Texas, Gutierrez did what he always does at a track, he worked hard in the mornings. Growing up at Finger Lakes, grooming, hot walking, galloping—this was how he was raised, and this was how he climbed to the top at Gulfstream and at Aqueduct. Calhoun recognized this and gave him a shot. With Churchill Downs building a new turf course in 2021, Calhoun had sent a string to Colonial Downs in New Kent, Va.
“Jose told me, ‘Go to Colonial, bro. You’ve got nothing to lose,'” Gutierrez said. “I left at 10 p.m. and got to Colonial at 6 in the morning and who did I work? Hidden Connection .”
Before racing in the 2021 Breeders’ Cup Juvenile Fillies (G1) and the 2022 Kentucky Oaks (G1), Hidden Connection won her 2-year-old debut in a maiden special weight race at Colonial. Then she went on to win the Pocahontas Stakes (G3) at Churchill—the second graded stakes win for Gutierrez and his first since winning the 2019 Tom Fool Handicap aboard Do Share .
“I knew this horse was really, really good but at first I wasn’t riding her (in races),” Gutierrez said. “I was just helping Bret with whatever Bret needed. Then Gabe Saez got hurt. It all happened right there. Saez was also supposed to ride Lovely Ride , but when he got hurt, Calhoun sent me as the emergency rider to Parx Racing to ride Lovely Ride and I won a stake. I came back to Colonial and won on Hidden Connection. And who else was there? Barber Road .”
Gutierrez guides Lovely Ride to victory in the 2021 Cathryn Sophia Stakes at Parx
The Texas plan was paying off. These were the horses who could take Gutierrez to Kentucky’s biggest races.
“(After Colonial) we went to Remington Park and Jose and I got a dope townhouse in Oklahoma City, so cheap too,” Gutierrez said. “I was there for two weeks, and one day Jose was like, ‘Pack your bags, you’re going to Kentucky, you’re on Hidden Connection. It’s now or never for you man.’ In Louisville, Jose slept on the couch and I slept on a little inflatable bed in a place on Southern Parkway. That was me and Jose.”
Gutierrez would guide Hidden Connection to a 9 1/4-length victory in the Pocahontas Stakes (G3) at Churchill that day and in November they would finish fourth in the Breeders’ Cup Juvenile Fillies (G1) at Del Mar.
Gutierrez celebrates aboard Hidden Connection after winning the 2021 Pocahontas Stakes
For the winter of 2021-2022, Hidden Connection and Bret Calhoun were heading to Fair Grounds. Barber Road, a stakes-placed colt at 2, and trainer John Ortiz to ventured to Oaklawn Park. Gutierrez and Santos decided to follow Calhoun to New Orleans, but the hope was to keep both potential Kentucky Oaks and Derby mounts.
Bouncing back and forth between Fair Grounds and Oaklawn, even heading to Gulfstream to ride Chess Chief for Dallas Stewart in the Pegasus World Cup (G1), Gutierrez and Santos juggled their goals. Gutierrez proved his mettle in 2021-2022, his first season riding at Fair Grounds, when he finished fifth by wins with 51. On the other hand, Gutierrez was gone many weekends, stunting his availability to breeze horses in the mornings and build relationships.
“My father told me, ‘You can be the leading rider at Fair Grounds, but you just can’t leave as much as you did,” Gutierrez said. “You have to stay and ride every day.’ My first full meet I left 20 or so days, but this year I only missed eight, and for my father there was a sense of pride at stake because he’s always wanted it for me. ‘Whether it’s at Aqueduct or Fair Grounds you need to be leading rider somewhere.'”
On closing weekend of his first meet at Fair Grounds, Hidden Connection was taking on 2-year-old Eclipse Champion filly Echo Zulu in the Fair Grounds Oaks (G2). Gutierrez had come so far over the past year and a half, but neither Barber Road nor Hidden Connection had won in their Derby or Oaks prep races. Any jockey, especially one still working to prove himself, would be nervous about losing the mount.
Sent off at 9-1, Gutierrez had Hidden Connection chasing the pace, caught three lengths wide, and in third as Echo Zulu led the pack. In the second turn, Gutierrez opened up his filly to make a move for the lead but could not measure up the odds-on favorite until she began to tire in the final strides. Hidden Connection lost by a nose.
“I was crushed with Hidden (Connection),” Gutierrez said. “Echo Zulu was the (2-year-old filly) champion and that race seemed like the only time I was going to be able to beat her. I thought I made the right move in moving early, but when I got there at the wire, the champ came back on me.”
This is horse racing, a sport where a centimeter difference cements you in history as a winner or a loser. Falling short of some goals in their first meet in New Orleans Gutierrez and Santos took the approach of continuing to knock at the door, confident it would open.
Persistence, Timing, and Redemption
Coming into Fair Grounds’ 2022-2023 meet, Gutierrez and Santos had two goals: to win the jockey title, and to find a 3-year-old that would take them back to Churchill Downs for the Kentucky Derby or the Kentucky Oaks. In order to win the title and find a top 3-year-old, Gutierrez and Santos needed to diversify barns.
Agents are limited to having two jockeys at any one track, and typically, that’s the full extent of their book. Santos represents eight riders, spread out at different tracks. It takes something more than just being able to ride to be a jockey for Team Santos, and much of the work of finding new barns to ride for landed on Gutierrez.
“It’s pretty much essential that they are able to market themselves in the morning because I’m not around like every other agent in the mornings,” Santos said. “To begin a relationship with new barns, I just specifically ask trainers for one horse, for instance Theboyzgalaxy for (Courtney Dandridge Jr.). I just went out and asked him specifically for that horse. They got to meet Rey when he rode the horse and from there they were like ‘All right, we like him and here’s some more.’ That’s usually how it works. I’ll do the research before I go ask for a specific horse. And from there they get to know Rey and it’s hard not to like Rey once you get to know him.”
In 2022-2023, Calhoun dominated the first half of the Fair Grounds meet, and Gutierrez was a big part of that, riding the majority of Calhon’s entries. But at this meet Gutierrez rode for a lot more barns than just Calhoun. Dandridge, Shane Wilson, Brendan Walsh, Joe Duhon, Steve Asmussen, Ron Faucheux, Eddie Kenneally, and several more.
“The day-to-day business this year was much better than last year,” Gutierrez said. “I met more people that I didn’t get a chance to ride for last year. It will keep growing and we’ll keep building relationships for as long as we keep coming back. Still, the biggest factor for me was clearly Bret lighting it up this year. I feed off of Bret, and I’ve been lucky to ride the majority of Bret’s horses.”
Enter Southlawn
After Gutierrez made a bold early move up the rail abroad Southlawn to win a February allowance level race, trainer Norm Casse entered the filly with star-potential in the Fair Grounds Oaks (G2)—her first stakes and her one shot to earn qualifying points for a start in the Kentucky Oaks.
“We’d been super excited about this filly the whole time,” Santos said. “Rey had liked her from the very beginning, from the first time he got on her he’s liked her a lot. She keeps getting better and better every morning, that’s what he kept telling me.”
Southlawn and Gutierrez win the Fair Grounds Oaks
Gutierrez had the jockey title wrapped up for over a week, but on the Saturday before closing day he had the chance to avenge last year’s heartbreaking loss in the Fair Grounds Oaks. With the mount on the 7-1 filly Southlawn, Gutierrez and Santos were one win away from another goal—finding a mount in the Kentucky Oaks.
Gutierrez needed to turn the page on Hidden Connection and be bold aboard his filly Southlawn. Settling early, Gutierrez guided his filly along the rail while never losing touch with the field. Southlawn showed her willingness to enter the scrum, but her jockey patiently let favorites Pretty Mischievous and Hoosier Philly battle it out as he positioned himself for a rally to the pair’s inside. When Hoosier Philly tired and dropped down to the rail at the top of the stretch, blocking Southlawn’s path, Gutierrez made a well-timed move off heels to bid for the lead outside of Pretty Mischievous. And Southlawn was there for him, as the filly surged past to win by three lengths, securing a spot in the Kentucky Oaks.
“This is the best feeling,” Gutierrez said. “This is why I do it. I love riding horses and I’m really happy.”
The Fair Grounds meet is over, Hidden Connection’s loss has been avenged, and the Oaks mount is secured. With Gutierrez’s first leading rider trophy in his hands, all the emotions that had built up over his sustained rally from winless at Turfway Park to 64 wins at Fair Grounds came pouring through.
“Jose changed my life in 2020. Bret Calhoun changed my life,” Gutierrez said. “I always wanted this and my dad always wanted this. So many people at Finger Lakes backing me in New York, so many people have been a part of me getting here. Jose pushes me every day. The horses have been amazing.
“Everyone on the backside who has helped me. It’s emotional because when you really want something and you think about it every day, you kind of get obsessed with it, and I’m not going to lie I was obsessed with it. This drove me every day when I was jogging, jump-roping, whatever. This is the best feeling. This is why I do it. I love it. I love riding horses and I’m really happy.”
With a jockey title and two straight mounts in the Kentucky Oaks, there’s no question that Gutierrez and Santos’s forward-minded tactics have worked. Where will their momentum carry them next?
“We’re on the trajectory to go to Saratoga but we still have to prove that’s a good decision,” Santos said. “We still have a lot of racing to go and we hope to prove we belong on that stage. But I think we do.”
When you are making your second run at something, maybe you realize that there is no such thing as perfect timing. Maybe the key is to be forward-moving always, as Gutierrez and Santos, trusting that momentum coupled with hard work will carry you to the wire. Timing is everything, but for the persistent, there’s always another run.
