In early 2022, Robert Costello was sitting in a parking lot while on a ski trip in New Hampshire when he received a call from Will Connell, who at the time was the U.S. Equestrian Federation’s director of sports programs. A few months earlier, at the end of 2021, USEF chose not to renew U.S. Performance Director of Eventing Erik Duvander’s contract, and the entire eventing program underwent restructuring. The 2022 FEI Eventing World Championships (Italy) was fast approaching, and the team needed an interim chef d’equipe for that championship.

Connell wanted to know if Costello would consider applying.

It wasn’t Costello’s first experience applying for the chef d’equipe/technical advisor position. Roughly a decade earlier, USEF was seeking a replacement for Capt. Mark Phillips, who’d held the role since 1993 and would be stepping down following the 2012 London Olympics. Costello joined forces with Phillip Dutton in a joint application, where Costello would take on the manager role while Dutton focused on the coaching aspect. They ultimately withdrew their application in March 2011, and David O’Connor eventually got the role. Though he appreciated the experience, Costello didn’t feel like he’d missed out.

“After that, and watching other people do that job, I was like, ‘I would never, ever, ever want to have that job,’ ” Costello recalls. “People would be like, ‘Oh, would you ever do it?’ I was like, ‘Absolutely not.’ I see how hard it is, and how fraught navigating everything that you have to [navigate] is.”

At the time of Connell’s call, Costello was exploring life away from high performance eventing for the first time in decades. After the 2021 Tokyo Olympics, he’d stepped down as chairman of the USEF Eventing Selection Committee for Olympic, World and Pan American Games, believing it was time for someone else to take the helm. He began ramping up his teaching schedule, considered purchasing some sales horses, and went skiing with his nephew.

But as he mulled over Connell’s request, he was intrigued.

“I said, ‘Well, it will be good just to go through the process of having to do [the application] and use that side of your brain and think about like how would you run a program if you were to do it,’ ” he says. “I thought it was really appealing. It was a very set amount of time. It was going to be a little bit crazy, and I don’t think the expectations were super high because the program was pretty much completely dismantled at that time.

“And then I got hired,” he adds.

A Whirlwind Few Months

USEF announced Costello had taken the position on April 13, 2022, and his contract was set to expire Sept. 30 that year.

“It was a little intimidating, the thought of trying to pull together that program, but incredibly fulfilling,” Costello says. “And I think what we didn’t appreciate is that we had some top riders with really excellent individual programs. They were forced to not lean on anyone else.

“They had had to really seek out the coaches that were going to work for them, and not just who was going to be kind of offered to them through the federation,” he continues. “It was so interesting how, when all that support went away, the riders really had to look at their own programs and say, ‘OK, well, there’s not going to be any real help here for a while.’ ”

Back in the early 2000s, when Costello was a member of the U.S. Eventing Team, the squad riders followed the same program. They all rode with Phillips—something Costello says was hugely beneficial for him—did gallops at set times and went to specified competitions. But in the new era of U.S. eventing, the chef d’equipe role was largely management, not coaching.

“It was amazing because the riders actually were able to basically show that their program works,” he says. “They don’t have to go to this event, this event, and do these exact gallops to go and win five-stars. So that’s one thing I’ve tried to carry through. I didn’t get hired to travel around the country and teach all these guys, and they have their programs. I’m there to help if they if they want my help, but absolutely I’m not the coach; I am the team manager, and I love it.”

In the lead-up to the world championships, Costello felt optimistic about their chances.

“I think people thought, ‘Why is he saying that we’re going to win a medal? The only thing we have to do is just qualify for the Olympics,’ ” he says. “I was so sick of hearing, ‘Well we’re going on an eight-year program to get back to the podium.’ That’s ridiculous. With this many riders with good horses, why would it ever take that long?”

At the beginning of 2022, the program was in shambles; by September, the team comprised of Tamie Smith, Will Coleman, Lauren Nicholson and Boyd Martin were climbing onto the podium at the FEI Eventing World Championships in Pratoni del Vivaro, Italy, to collect team silver—the first team medal in 20 years.

“He’s quite direct and very stringent but also empathetic. I think it’s a good combination,” says Smith, who first got to know Costello when he was a selector and later as chef. “He’s running a tight ship, but he’s also understanding and will listen to what you have to say.”

Growing Up In An Eventing Mecca

The youngest of five children, Costello grew up in Hamilton, Massachusetts. Though neither of his parents were into horses, living in an eventing mecca meant riding was a natural direction. During the 1970s, the U.S. Equestrian Team was headquartered at Gathering Farm in Hamilton, and the famed Ledyard Farm Three-Day Event ran in full force nearby, drawing the likes of Phillips and Princess Anne from across the Atlantic.

Team riders based at the headquarters full time, and Chef d’Equipe Jack Le Goff promoted putting his riders into high pressure situations regularly. Several mornings a week the stables were open for tours,and during summers Le Goff would set up a show jumping course on the front lawn of the big house and invite locals to watch team members jump. Having a front row seat to the training and management of top horses inspired a young Costello to maintain a high standard.

“It was an incredible experience, growing up in that town at that time, because there was Groton House and Flying Horse [events] and so many very influential people within the eventing world. Neil Ayer and General [Jack] Burton, they all lived up in Hamilton at the time,” says Costello. “I was friends with Jack Le Goff’s kids; we went to school together. So it was kind of a cool time to be living up there.”

Costello’s older brother started riding first, and since Costello was several years younger, he never knew a life without horses. Though his family wasn’t wealthy and getting saddle time meant hard work, he said his parents were supportive of all their children’s athletic pursuits.

As a child Costello didn’t define himself as a participant in one discipline. He hunted with Myopia Hounds, rode show horses, and evented at a busy boarding, hunting and lesson stable that supplied him with a steady string of horses.

“I was able to ride all sorts of different types of horses all the time. They weren’t all great, but every single one of them was an education,” he says. “I was really, really lucky. I think that’s hard for people; when I see young people trying to do it on one horse, and they get that one opportunity maybe once every three weeks to get out there and compete andtry to hone their skills. So I always say, ‘Try to get on as many horses as you possibly can, good or not.’ ”

But riding wasn’t his only interest. For a long time, his most intense activity was piano, and it led to a full scholarship to the University of Massachusetts in Amherst. During his junior year he went abroad to ride, and when he returned he had a revelation: He didn’t believe he was good enough to be a concert pianist and couldn’t picture himself teaching either. So he switched majors to mass communication, and by minoring in music was able to maintain his scholarship.

“I’m so glad that I went to college,” he says. “Even if you go to college and you never do anything with it, and you want to go into the horse business, it’s always really good to be able to be in a room with anybody and never be made to feel like you’re less smart or, oh, you’re just doing horses because you couldn’t do anything else.”

After graduation, Costello considered going into journalism, but given how much he enjoyed riding, he gave himself six months to a year to test the waters. His future was cemented when Leila Clay, who rode at the farm where he ran a summer program, went into business with him. He partnered in C&C Sporthorse at Tanglewood Farm in Southern Pines, North Carolina, for roughly 20 years. He now runs ROC Equestrian out of Mark Weissbecker’s Winter Brook Farm, also in Southern Pines.

“I kind of just fell into it, and it wasn’t easy,” Costello says. ”But I don’t know if I would have been able to cut it on my own, if I didn’t have that support pretty early on, because I definitely had no interest in being a starving horseman, like, at all. [I] totally would have done something else if that didn’t work out, and it did. Super thankful for that.”

An Unexpected Goal

Competitively, Costello describes himself as a late bloomer. He estimates he did his first advanced at 28 or 29 and his first four-star start at 32. He’d done two five-stars ahead of his Olympic debut in Sydney in 2000, the first of which he called “a disaster,” but he never worried whether he was falling behind the timeline.

He never had great Olympic ambitions, preferring to focus on the process, and it’s a principle he likes to impart on young riders.

“When someone is 14, and I ask them what their goals are, and the first thing they say is, ‘Going to the Olympics,’ I’m like, ‘OK, that’s great, but I’m talking about, like, next week, next month, this year, the next five years,’ ” he says. “I think that’s what keeps you going. It’s great to have that kind of goal somewhere off in the distance, but I think short-term planning is a good thing. It keeps you focused.”

In Sydney, the eventing individual and team competitions were separate, and the U.S. sent seven pairs across both divisions, which provided more opportunities. Competition for those spots was still fierce, Costello says, with some of the top riders having multiple horses in contention. But there was attrition due to the lengthy travel required, and with horses dropping out, he earned his ticket to Sydney.

“We were there for a couple of months, and as we kept getting closer and closer, it was looking more and more likely that I would probably compete, which I didn’t go there with that thought at all. It was just to get the experience,” Costello says. “Everything kind of worked, and I had a really great Olympic experience, so I was very fortunate.”

With a two-week quarantine in the U.S., followed by a three-week quarantine once they were in Australia, the U.S. riders spent a lot of time together, and Costello relished training beside his teammates daily and learning how they did things.

Jim Wolf, who was the USET/USEF director of eventing and eventing chef de mission beginning in the early 1990s, first got to know Costello through the team. They’ve since become good friends, and Wolf recalls Costello’s affable personality as an asset through those long months.

“What always stuck out to me about Bobby was that he was really great on the field and off the field,” says Wolf. “He was a very good competitor, but he was also just a really good presence around the training programs and when he was on the team just because he’s a great influencer. He really helped keep the program positive and moving forward.”

Costello’s mount for the Olympics, Chevalier, didn’t come to him with international intentions. The chestnut gelding’s rider Amanda Pirie Warrington, with whom Costello grew up, died in 1997 as the result of a fall, and her mother Deirdre Pirie and husband Danny Warrington placed her horses with various riders to sell.

“I remember one time asking Amanda what was her favorite of her horses, and she said Chevalier,” Costello says. “She called him ‘Charlie,’ and she said, ‘He’s not the flashiest mover; he’s not the scopiest jumper, but he always, always wants to perform, and he’s careful, and he’s fast.’ He was a Thoroughbred and just super, super consistent. So, when I was asked to take on Charlie, it was great because I knew that she adored him.”

But Charlie had a couple of old tendon injuries from his racing days, which made buyers reluctant. When he was still unsold heading into 2000, Costello asked Pirie if she would hold off on selling the gelding, and she readily agreed. Charlie and Costello were chosen to compete as individuals and finished eighth. After the Olympics, Costello showed Charlie for three more years, contesting Burghley (England) once and Kentucky several times before the gelding’s retirement at 14. He spent the remainder of his life with Costello.

While he fell into his first Olympics, Costello made a more strategic effort heading into Athens. Knowing Charlie would be a longshot, he purchased Dalliance with Greece in mind. The pair went to the 2003 Pan American Games at Fair Hill (Maryland), where they were on the gold-medal team and placed seventh individually.

Though they missed the 2004 Olympics, Costello says Dalliance gave him plentiful opportunities throughout this career.

“I have had other horses that had probably way more natural ability than those two horses put together, but things don’t work out; soundness is always a big issue,” he says. “I think I was lucky to have two really good ones and a lot of really cool horses on the way.”

Hanging Up His Boots

While Costello loves the sport, he always knew he wouldn’t be a serious rider forever. In 2010 he rode in his last Fédération Equestre Internationale event, and he hasn’t shown in a national even since 2013.

“I even remember having a conversation with David O’Connor when we were in Australia [about] how long we both thought we would keep competing, and I said, ‘Yeah, I’ll probably do this seriously until I’m about 40 or so,’ which now seems so young,” he says. “I competed at the top level until I was about 45, and I do feel 40 would have been just right because I really wanted to concentrate on my business, and I love bringing along the young horses and coaching. I’ve never felt like with anything I have to do it forever.”

While riding can be a lifelong pursuit, and there’s many riders still chasing team selection into their 60s, that was never something Costello desired.

“I don’t regret a second kind of retiring fairly young from top competition, really not at all,” he says. “Even though I love it—I’ve been around it and been involved with it ever since then—but for me, the competing was a great part of my life, but I never thought that I would do it forever.

“It’s the year on year just being in that [mode of] getting ready for Kentucky or getting ready for a team thing or getting ready for Badminton [England] or Burghley,” he adds. “Every single day, you just feel that kind of intensity—maybe I carried it too much, but I respect people that are still living on that in their 50s.”

While he was no longer competing at the highest levels, Costello kept involved with high performance through governance. He chaired the USEF Active Athletes and USEF Eventing High Performance Committees, was a member of the USEF, USEA and USET boards and was a championship selector from 2013 to 2021.

He didn’t actively seek out positions on committees, but his inclusion on the U.S. team brought attention his way, and he found he enjoyed the knowledge he gained. He believes being part of these committees and knowing the players was beneficial when he took the chef d’equipe position.

“One thing that made it less daunting, even though it was pretty daunting, was that I’d been, for better for worse, part of the structure of eventing for a really long time,” he says. “So I knew who everybody was and knew how the committee stuff worked, which is not easy to navigate if you don’t know about it.”

Wolf describes him as the right person for the job, able to remove roadblocks for athletes so they can focus on their job, while keeping the atmosphere light.

“With Bobby there’s really not pretense. He is what you see,” says Wolf. “He’s just a really kind, generous guy, and happy. Bobby’s fun. I used to say this a lot, ‘You can’t lose sight of the fact that this is still a sport that’s meant to be fun.’ It’s serious business, but you have to have joy in doing it to be successful, and Bobby brings a lot of joy to that job.

“Someone said to me one time, one of my mentors said, ‘Just remember: KFC,’ and I was like, ‘Kentucky Fried Chicken?’ They’re like, ‘No, be kind, be firm and be clear,’ ” he adds. “Those are the three things you need to be successful in that job, and he is those things.”

Running A Tight Ship

The chef job appeals to Costello’s organizational side. He’s always run all aspects of his own business, including all office and accounting work, and he never had someone else fill out his entries. “I don’t know which it is: either I really like doing it, or I really hate letting other people do it,” he says with a laugh.

He books all his team-related travel and thrives on the correspondence portion of his role—a skill he believes his mass communication degree helps with. His job is to be a great observer and find ways to support the athletes in their pursuit of medals, he says.

“I feel like anything that I can do to just be supportive of that is my job,” he says. “Whether it’s somebody who wants to talk about their fitness schedule for their horses or for themselves, how to maybe communicate with this certain owner or, ‘I’m thinking that I might need to change coaches.’ I think people trust that I will be there for them with as much input, or as little, as they might want.

“I think I have a good personality to develop relationships with the people that are going to come together and hopefully do great things with the team,” he adds. “I think a strength of mine is my natural—I always call it like pragmatic optimism. It’s not just like, ‘Everything is going to be great,’ but, ‘If we do this, this and this, we should just expect it’s going to be good.’ ”

Costello says he enjoyed his time as interim chef, save for one tense weekend at the final mandatory outing at Great Meadow (Virginia) prior to Pratoni. An incredibly dry summer led to subpar footing conditions, and the riders were on edge. Costello remembers driving home after that August weekend thinking the role was a good experience but not something he’d do forever. Once the team arrived in Vittel, France, where they completed their final training sessions, the unsettled feeling from Great Meadow dissipated as the pieces came together.

“Minus just a couple of growing pains very early on in my interim position, since then I haven’t looked back, and it’s just been incredibly, weirdly smooth,” he says.

Supporting a vast number of personalities, from athletes and owners to farriers and veterinarians, isn’t an easy task, but Smith says Costello navigates those challenges well.

“I think everybody has a very healthy respect for him in that they know that they can’t kind of step over that line,” she says. “But also we’ve known him for so long, and we have a respect that he actually did it himself, so he understands the stress level involved with representing your country. He’s adorable, and everybody loves him. He’s very well liked and respected throughout the industry.”

Following Pratoni, Costello decided to put himself in contention for the position long term. He recognized success in Italy didn’t make him a shoo-in, but going through the process and developing a four-year plan for the high performance program was a challenge that appealed to him.

“I was absolutely under no illusions that I was automatically getting hired,” he says. “I felt really excited when I actually got the full-time position, because I felt like I really had to work for it and show that I wasn’t just the person [who was a] stop-gap measure. They had faith in what I had done, and what I was proposing for the future.”

So far in his tenure, in addition to the world championships medal, the U.S. team was second at the Aachen CCIO4*-S (Germany) in 2023 and earned team silver at the 2023 Pan American Games (Chile).

With the 2024 Paris Olympics on the horizon, Costello has prioritized giving high performance athletes ample opportunity for growth. When Gregory Bodo, who is designing the Olympic show jumping track alongside Santiago Varela Ullastres, set courses at the World Equestrian Center—Ocala (Florida) in March, many of the potential team riders jumped a 1.30-meter round there. They watched and walked courses for all the classes Bodo designed that day to get a feel for his style—a lesson Costello learned from Pratoni.

“I think we were caught a little off guard honestly at Pratoni [in] that we didn’t know that course designer at all, and he set gigantic, technical track,” he says, “and, in retrospect, we should have maybe found out who this guy was, and how he designed, even if it’s just being able to watch video.”

Though his chef duties keep him busy, Costello has a young horse he rides for Weissbecker, though he doesn’t feel he has time to devote to riding seriously. He still enjoys playing piano and tennis, and spending time in downtown Southern Pines. (He jokes he should work for the city’s chamber of commerce as he passionately tells visitors which local restaurants and shops they should explore. “I should just write a travel book that they can give everybody when they come to the horse park: ‘These are Bobby’s recommendations,’ ” he jokes.)

He’s cut back on teaching, because he doesn’t want to leave students without help if he can’t be at their events. But Costello still enjoys that part of his profession, whether it’s helping an 81-year-old woman get ready to compete beginner novice or working with upper-level athletes.

“I don’t really care about what level someone’s competing, but I do care that they’re passionate and go about it the same way as a professional would,” he says. “I definitely am not for everyone, but it’s really fun to help people.”

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A version of this article originally appeared in the July 2024 issue of The Chronicle of the Horse. You can subscribe and get online access to a digital version and then enjoy a year of The Chronicle of the Horse. If you’re just following COTH online, you’re missing so much great unique content. Each print issue of the Chronicle is full of in-depth competition news, fascinating features, probing looks at issues within the sports of hunter/jumper, eventing and dressage, and stunning photography.