Longtime Area I event trainer, Chronicle of the Horse advertising account manager and founder of “Buck Off Cancer” Jess Halliday died on Oct. 26 after a hard-fought battle with colon cancer. Here, her friend, fellow eventer and Chronicle colleague, Caitlin Calder, shares her memories of Jess and the legacy she leaves.

While no amount of time with Jess was ever going to be enough, she did more, taught more and loved more in her short 33 years than most would be able to in a hundred. She showed me and so many others what it means to be an amazing person, incredible friend and to live life with abandon.

Jess’ motto was always, “Be the person you needed when you were younger.” She was that and so much more to the countless kids who came through her lesson program: a coach, a friend, a role model. Her barn became a haven to so many young riders who shared her same passion.

She was a guiding light through their formative years. She taught them to ride, of course, but more importantly she taught them to be good, kind, empathetic people. She taught them to be gracious competitors and show kindness and compassion to everyone. She taught them to go outside their comfort zone and to make the time for the things that mattered most, because tomorrow is never promised. She taught them to dig deep, work hard and never give up, because the best things in life never come easily. She did this all by being the incredible example of the human being she was. Without realizing it, Jess left her thumb print on their hearts while helping to mold dozens and dozens of these horse crazy kids into brave, passionate, hard-working, empathetic young adults. They are her legacy.

Being true to form, Jess unknowingly extended that motto of hers, “be the person you needed,” to all those she knew—and often those she didn’t—when they were broke, when they were down, when they were heartbroken, when they were stuck, when they lost confidence, when they needed a friend or when they just needed a leg up.

About a decade ago I returned to Area 1, after gaining some upper-level eventing miles and much-needed years of coaching and training in some top programs, with the idea that I’d give it a go as a professional in the sport. Jess and I had seen each other around at the competitions but were nothing more than casual acquaintances at the time. Out of the blue, she messaged me over Facebook, offering to host a clinic for me so that I could start making some money. I was completely blown away by her offer. While many professionals might regard a newcomer to the area as a potential threat to their own clientele, Jess was the opposite.

I had never met such a selfless person who focused more on lifting up those around her. From then on, Jess and I were fast friends.

Jess Halliday, left, and author Caitlin Calder. Photo Courtesy Of Caitlin Calder

Our years of friendship saw countless nights out in Aiken, South Carolina, where many poor decisions were made. Last-minute, 25-person dinners at a packed Whiskey Alley, where Jess used her magic to somehow make sure her special table was always available. No matter the chaos, or who was around, she was always able to make each of us feel like the only one in the room. Jess spent many freezing, soaking-wet weekends at Pine Top Horse Trials in Georgia, where she somehow was able to compete up the levels herself while simultaneously coaching and corralling her 800 students and still managing to be ringside for all of her friends’ rides.

Jess loved to punctuate the years with random escapades—to jump out of perfectly good airplanes, ride bulls and cage dive with sharks— because galloping at solid obstacles for a living wasn’t enough of an adrenaline rush for her.

Fast forward to a few years ago: I’d gone through a career pivot and am now working for The Chronicle of the Horse (not as a writer, as I’m sure all of you who have read this far have figured out), and Jess was in the midst of her battle with cancer. Unwilling to accept donations to help with the costs of her treatment, she already had started an apparel line called Buck Off Cancer which helped fund her treatment (and which has since been formalized as a non-profit to help others fighting cancer).

Jess  confided in me that the treatments were taking their toll and that she was in need of an income that was a bit kinder on her body than the daily grind of the barn. We had an open position in the advertising department, and I immediately pushed for her to be considered. Jess’ background made her a natural fit for the role. More importantly, I knew that with her incredible work ethic and charisma, she would thrive in any position.

It was the very least I could do to even start repaying her from the extraordinary kindness she showed me when she offered me a leg up, perhaps when I needed it most, all those years ago.

While we were no longer living in the same state and riding at the competitions together, having the chance to work with Jess the last couple years of her life and to have that time with her was the most incredible gift.

As I sit here with tears in my eyes, reading through the endless Facebook tributes, with the #belikeJess hashtag trending alongside her #buckoffcancer brand, it’s become increasingly clear that her students won’t be her only legacy. Because we won’t just honor Jess by retelling countless stories of her insurmountable kindness and generous spirit, her unparalleled sense of adventure, or her compassionate nature and her innate ability to lift up all of those around her.

We will keep her memory alive by continuing these stories and adding more chapters to her book. Because when we take her with us and make the effort to really #belikeJess, we pay it forward by offering a helping hand to someone unexpected, lift up those around us instead of just ourselves, take that leap of faith and jump into the deep end (or out of a plane)—that will be her legacy. That is how Jess’ memory will live on forever.

Family and friends are invited to remember and celebrate Jess’ life with a walk-through visitation from 2-7 p.m. Friday, Nov. 5, at Mulhane Home for Funerals, 45 N. Main Street in Millbury, Massachusetts. 
Her Funeral Mass will be celebrated at 10:30 a.m. Saturday, Nov. 6, at St. Mark’s Church, 359 Boston Road in Sutton, Massachusetts.
For the funeral, equestrian attendees are encouraged to consider wearing show attire, and others to dress casually and consider wearing any Buck Off Cancer apparel or black and blue clothing (Jessica’s cross-country colors) they have.
In lieu of flowers, the family requests contributions may be made to Buck Off Cancer, P.O. Box 113, Stow, MA 01775.