Building Confidence with Hunter Trainer Tom Brennan

Hunter trainer Tom Brennan taps the power of positive thinking for himself and his students.
Tom Brennan and Gramercy Park at the 2013 Upperville Colt & Horse Show | © Teresa Ramsay

When Catherine Jackson’s trainer, Tom Brennan, entered her in the handy hunter class at the 2012 Upperville Colt & Horse Show, she thought it was just a warm-up for her Junior Hunter classes. “I had no idea that there was a $10,000 prize. Tom helped me come up with a really cool, hard course. I just went in and had a lot of fun, and we ended up second,” she remembers of her Paul & Eve Go As You Please Handy Hunter round.

Two years earlier, Catherine never would have imagined tackling a class like this with such an assured, easygoing attitude. Her first horse habitually refused jumps, which destroyed her confidence. “We didn’t have the budget to buy a fancy horse, so we bought a green one with potential. But I was 12 and did not have the leg to support him to the higher jumps. I felt like I couldn’t see distances. I was always second-guessing myself.”

That’s when she started training with Tom. He encouraged her family to sell the horse and helped them find a more reliable, experienced mount to lease named Providence, owned by Mary Keevil. “Before that, I felt like I was forcing my horse to go in the ring and do things he didn’t want to do,” says Catherine. “Tom brought the joy back into riding for me, showing me that my horse could enjoy his job.” Over the next three years, Catherine and Providence competed successfully in many divisions from equitation to Junior Hunters and U.S. Hunter Jumper Association International Hunter Derbies.

“Tom fosters a bond between the horse and rider,” says student Catherine Jackson with Providence and Tom. | © Courtesy, Tom Brennan

This is the sort of joy and confidence Tom, 32, instills in all of his riders, whether they follow the traditional path through Children’s and Junior divisions or a more roundabout route like his. Although his family supported his interest in horses at a young age and enabled him to take lessons at a local hunt-seat barn in Worcester, Massachusetts, they didn’t have the wherewithal to buy him a horse or take him to shows. In fact, before he entered Stonehill College, he says, “I didn’t even know that side of the horse world existed. I had no competitive aspirations. I just enjoyed being around horses.”

Not even aware that Stonehill had a riding program, Tom applied to the college for its strong liberal arts program and relative proximity to home, which was important, he says, because “I was very close to my grandmother and helped take care of her.” He signed up for the riding team as soon as he learned about it in the beginning of his freshman year. “By their standards, I was still quite novice. Sheila Murphy was a super coach. She organized rides to the barn for you if you didn’t have a car.”

The team quickly became his family away from home. “I made some of my best friends from that team,” he explains. By the end of his college career, Tom had won two individual championship titles at the Intercollegiate Horse Show Association Nationals and had captained his team to the IHSA team championship title in 2002–03. Meanwhile he’d studied hard enough to graduate cum laude with a degree in psychology. “The studies always came first,” he says. “My parents did not tolerate anything else.”

In addition to taking lessons with the team, he bought a horse and worked off the board in a local stable. It was in this barn that he met his future wife, Tracy, a riding instructor and former member of the University of Massachusetts’ IHSA team. He also met equine massage therapist Jo-Ann Wilson, who became a good friend and, eventually, the key to his future career. “I was on track to become a counselor for at-risk youth,” he explains. “I’d interned doing that outside of Boston. But I decided to postpone grad school. I wanted to go clear my head and do something else for six months or a year. And Jo-Ann said, ‘I know this guy in Virginia who does horses and goes to shows. You could probably learn a lot from him.’”

Tom Brennan and Purple Heart at the 2012 Middleburg Classic Horse Show. | © Teresa Ramsay

That trainer was champion hunter rider and U.S. Equestrian Federation “R” judge Tony Workman. Basing his training business, Winter Hill Farm, on Lynn Rice’s beautiful property in Hillsboro, Virginia, Tony had a reputation for producing quality young hunters and coaching adult amateurs to success at the top shows. He hired Tom in 2004 as a groom but gradually offered him more and more opportunities to ride. At first, Tony says, “Tom was kind of riding off the seat of his pants, but he had all the right instincts. He had really great hands and the horses liked him. And he really watched me ride—watched every move the horses made and how I did it. He still does that today.”

“Having someone like Tony to watch is huge,” Tom says. “He’s always been a great mentor in that he’s allowed for growth. He does that with his horses and with the people who work for him.”

From the beginning, Tom impressed his new boss with his commitment to family. The summer he joined the farm, his father was diagnosed with multiple sclerosis. Tony remembers, “He was supposed to start the first of June, but he asked if he could start in September because they had just found out about his father. He comes from a really strong family. I think that’s why our partnership has worked so well. I always feel that the people in my stable are like my family.”

Fake It ’Til You Make It
As Tom’s role expanded at Winter Hill, he replaced his original career plans with a dream to become a professional trainer. Five years after he joined the stable, Tony was sidelined by illness. “I stayed home, and Tom took the horses on the road. He held our business intact, and we just kept rolling. That’s how we work. We take care of each other.”

Tom first started working as a groom for Tony Workman (left) at his training business, Winter Hill Farm, in 2004. Gradually Tony offered Tom more riding opportunities. | © Courtesy, Tom Brennan

While on the road, Tom was often made aware of his atypical path to the professional ranks. “People would ask me, ‘Who’d you ride with as a Junior?’ Sometimes it was easy to feel like you didn’t belong because you hadn’t gone to equitation finals or hadn’t had a Junior Hunter. I kind of kept my head down, doing the best I could. I was willing to fake it until I felt like I belonged.”

“Sometimes you do have to fake it,” says Tony. “That’s part of show biz. That was one of the first things I mentioned to Tom. I said, ‘Do you think I see every distance?’” Possessing a natural confidence aided Tom’s speedy rise to the top, Tony adds. “He’s always been confident. And doing the team at school, having to get on different horses, helped.”

Good timing helped, too. As Tom was gaining experience in the show ring, Tony was finding new horses for Lynn to ride in the Amateur divisions. They gave Tom the ride on these top-quality horses in the professional divisions. He qualified for Indoors for the first time on Dividend, then rode Gramercy Park and Purple Heart to multiple major championships. In 2012, Gramercy Park was named the USHJA World Championship Hunter Rider Program Hunter of the Year and Tom was named the WCHR National Emerging Professional Champion.

Riding such special horses gave Tom’s career a tremendous boost. “The pressure skyrockets,” he says, “but so do the learning opportunities. With exceptional horses, it’s humbling to know that you’re usually the weak link. You’ve got to follow their lead. But that gives you confidence over years and years.”

Making Learning Fun
With Tom on board, Tony was able to expand his business, taking on more Junior riders. Drawing on his psychology background, Tom found ways to make learning fun for both kids and adults. He started giving the riders weekly quizzes on topics such as horse care and anatomy and initiated scavenger hunts at horse shows. “They love it,” he says. “They get a set amount of time to find as many things on the list as they can, then take pictures of them on their phones and bring them back. So, instead of sitting there for five hours and fretting about the long run to a single oxer, they can go run off some steam.” He includes items that help to make his riders savvier competitors. For example, he explains, “at a recent show, they had to find a guy named Steve. Well, Steve was their in-gate guy. So they had to figure out how to introduce themselves to him and get checked in and learn their course. Another thing was to find a shoe that wasn’t attached to a horse. So they had to figure out where the blacksmith was.”

Tom and Gramercy Park collect blue at the 2012 Washington International Horse Show. That year, Gramercy Park was named the USHJA WCHR Hunter of the Year and Tom was named the WCHR National Emerging Professional Champion. | © Shawn McMillen

In all of his teaching, Tom relies on the learning-behavior science he studied in college—“how you support that process and design experiences around it. I spend a lot of time in my own head going over an examination of small failures. If I can get students to accept that what they’re calling a failure may be just a necessary part of learning and improving, they seem to do better. I remember a long time ago hearing someone say, ‘Lose a class but don’t lose the lesson.’ And that has always stuck with me.” He follows what he calls the Monday rule. “Big problems at a horse show on Sunday always look different on Monday morning. In our next lesson, whether it’s three or four days or a week later, we go back and review what happened when blood pressure’s down and heads are cool and they can actually think.”

To help students feel confident, says Catherine, now a University of Virginia sophomore, “Tom fosters a bond between the horse and rider. He asks you, ‘How’s your horse feeling? Do you feel the difference in his jump?’ He helped me understand my horse better than I had ever understood a horse before.”

He also trusts his riders’ judgment, she says. For example, he let Catherine decide when her horse had had enough warm-up before a class. “Tom is always very conscious of saving the horse’s energy. We just work on getting the horse’s form in good jumping style. One time, I said, ‘I feel really good,’ after the first warm-up jump. He let me go right into the ring—and we won the class. I think that trust he had in me helped my confidence level.”

Tom has led by example as well, showing his riders how to handle the inevitable public scrutiny that accompanies successful careers. Last spring, a photo of him jumping a horse in competition was posted on Facebook, which invited the typical social-media critiques, some of which were extremely derogatory. The next morning, Tom posted a printout of the comments in the Winter Hill tack room, along with the following notice:

Tom and student Victoria Flagg, who rides in the Amateur-Owner divisions, share a laugh. | © Courtesy, Tom Brennan

“Attention: Kids of Winter Hill. This is what some people thought of a round that scored an 88 this week … You will meet many ‘experts’ in life … most of them sit on the sidelines where it is safe to say, ‘They are not good enough.’ The only one who can tell you ‘You can’t’ is you—and you don’t have to listen! No one can make you feel inferior without your consent. We do not let anyone else make this sport unfun for us. The only expert opinion that matters when you ride is right underneath you. Listen to your horses and treat them with tact and kindness today and I will be proud of you. Good luck and have fun.”

School Comes First
Just as his parents made school a top priority for him, Tom stresses its importance with his students, encouraging them all to attend college. “I’d call it a necessity,” he says, even for riders who hope to have horse-related careers. “You’re going to be around successful people who are educated—your clients, owners, students. They want a peer that can look them in the eye and speak on the same level. The college experience offers you these skills as well as analytical problem-solving skills and an ability to see the big picture and understand what small steps you need to accomplish it.”

Winter Hill accommodates the busy schedules of high-school students, says Catherine. “They are always available to ride the horses during the week if you have a lot of schoolwork but also encourage you to come out on the weekends and give you multiple horses to ride, so you can make up for not riding as much during the week. Tom always says, ‘If you need to do homework tonight, definitely do that. You can cancel your lesson.’”

To help kids control their nerves on show day, Tom encourages them to focus on him, telling them, “Take a moment to remind yourself that you’re lucky enough to even get to do this and that it’s supposed to be fun. No one else gets to have a space in your head. It’s your choice of how you’re going to act that day.”

He also encourages the same team spirit he enjoyed in college. “If one kid’s showing and you’re not busy doing something for your horse, you need to be at the ring, clapping and supporting that kid.”

Tom rides Second Year Green Hunter Trump Card at the Washington International. | © Shawn McMillen

One of Tom’s goals now is to incentivize riders with limited resources to continue competing in the sport, even if they don’t have the advantage of riding multiple horses and being home-schooled. “Where would we be without the Tony Workmans, Jack Towells and Geoff Tealls?” he says. “They were not wealthy or blessed with a string of horses as Juniors—and now they’re industry leaders.” Last October, he helped the Pennsylvania National Horse Show launch the Claire Mawdsley Scholarship and Rider Recognition Program, which awarded scholarship checks and prizes to the highest-placed riders in the four Junior Hunter divisions who attended traditional brick-and-mortar high schools on a full-time basis. Tom named the program after a Winter Hill Farm working student who died in a car accident on her way home from a horse show. “Claire was such a good role model for the other kids in the barn,” he says. “It was so fitting to attach her name to the program.” 

Tom’s commitment to Claire’s memory is indicative of the relationships he fosters with all of his students. “Making your horse family your actual family is also important,” he says. His first instructor, Bonnie Robinson, still travels to the show circuit in Gulfport, Mississippi, to help him for a week every winter. Tony, who was a groomsman in Tom and Tracy’s wedding, sees Tom as family, too, saying, “He could have been anything he wanted to be. I’m glad he picked the horse business because it’s been really nice to work with him and develop him. I look forward to going to work with him every day.”

Branching Out
Active on various U.S. Hunter Jumper Association and U.S. Equestrian Federation committees and boards, Tom Brennan says that he wants to “make sure there is always an avenue for people like me” and “to ensure that the industry—the shows, governance groups, etc.—serve the sport, rather than the sport serving the industry. If we can make it a sport again and all that word encompasses—sportsmanship, ethics, honor—I think we’ll be better off and will see more opportunities for everyone.”

Exploring another role, Tom also served as the official commentator for the USEF Network’s coverage of the 2013 and 2014 Pre Green Incentive Championship and U.S. Hunter Jumper Association International Hunter Derby Championship as well as the 2014 World Champion Hunter Rider Finals. He aims to keep his commentary positive, just as he believes all judges should, “trying to find ways to give horses points, rather than just take them away by always saying, ‘Here’s another mistake you made.’”

As busy as he and his wife, Tracy—who recently started her own training business near Washington, D.C.—are, they make a point to find time for each other. “My wife’s very good at that,” Tom says. She’s really good at hitting the recharge. Horses can contribute to our lives, but the horse industry has a way of taking away from it sometimes, too. And if that happens, we need to find a beach!”

To learn more about the Claire Mawdsley Scholarship and Rider Recognition Program and how to donate, go to to the “Exhibitors & Entries” tab.

This article originally appeared in the June 2015 issue of Practical Horseman.

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