Portraits by Kirsten Ziegler
Clad in her sparkling white Sync Equestrian Dragon Rhinestone full-seat breeches—a striking contrast against her mount, a black Oldenburg gelding—Cyndi Jackson immediately caught the attention of the crowd during the FEI Grand Prix Freestyle CDI3* at HITS Del Mar on March 22, 2026. As the first notes of Justin Timberlake’s “SexyBack” echoed across the arena, feet began tapping, hands clapped in rhythm and smiles spread across the stands.
Florisson, whose barn name is Jack, is owned by Ann Damiano, a dedicated client who has been training with Cyndi for over two decades. When it came time to select the music for Jack's Grand Prix debut, Ann took the lead. “Ann loved 'SexyBack,' so Marie Medosi from RaveHorse Productions created a freestyle centered around a boy-band theme,” Cyndi explained. “We wanted something that people would instantly recognize.”
Snippets from “Cake By The Ocean,” “Bye Bye Bye,” “As Long As You Love Me” and “Can’t Stop The Feeling” rounded out the rest of the routine. Beyond the crowd-pleasing soundtrack, Cyndi and Jack were on a mission to capture qualifying points for the upcoming US Equestrian Open in Thermal, California.
Watching Cyndi command the arena in the eye-catching breeches—or seeing her in an evening gown—one might assume she enjoys dressing up. “I’m actually not a very blingy person,” Cyndi laughed. “It takes a lot for me to get dolled up. I’ve owned this gown for nine years and only worn it once.”
In fact, those sparkly breeches were inspired by one of her young riders, Nicola, who was showing in them first. But Cyndi doesn’t need to add glitz and glam to impress with her riding; she’s already got things like cherished sobriety, 100-mile races, 115-degree heat and homeschooling.
That down-to-earth mentality is the foundation of a rider who didn’t have early access to horses. “Growing up in Arizona, I didn’t start riding until I was about 11,” Cyndi said. “My mom and I used to go bowling every Sunday because of discounted rates from my dad’s company. One weekend, my dad brought home discounted tickets for horseback riding, and we never went bowling again! It became our Sunday routine, then Saturday and Sunday, and eventually Wednesday nights after school.
“My dad was adamant that we shouldn’t own horses, so we found a horse to lease. We told him the owner was a foreign exchange student who had to leave the horse behind, reassuring him that we could never buy her,” Cyndi continued. That lease horse was Maxine, a 4-year-old Tennessee Walker/Quarter Horse cross. “I had Max from when she was 4 until she was 33. The owner eventually gave her to me. She wasn’t a conventional breed for dressage, but I wasn’t doing dressage then—I was running around the desert on trails, making sure I didn't get bucked off!”
Without formal riding lessons early on, Cyndi’s equestrian education was defined by childhood ingenuity and pure fun. “I couldn’t sit the trot well, so I learned to ride bareback. It was just me and a group of kids at this small ranch, chasing each other around the arena and playing broomstick beach ball polo,” she said. “Eventually, someone mentioned that my horse wasn't cantering on the right lead—I didn't even know that was a thing! I started taking basic flat lessons because I wanted to help her learn.”
From there, Cyndi dabbled in jumping, eventing, barrel racing and even chasing cows aboard her trusty mare. “We tried everything until we found what suited her best. I would have pursued any discipline she excelled at because my primary focus was my relationship with the horse.”
Cyndi’s path shifted when she was 16 years old, competing at the Training level in eventing. “Christopher Reeve had his eventing accident and broke his neck. I decided to stop eventing and focus entirely on dressage. I am a dressage trainer today because that was the discipline where my heart horse felt most comfortable.”
Together, Cyndi and Maxine proved that heart and correct training matter far more than pedigree. Taking lessons every couple of weeks with a local trainer, Cyndi earned her USDF Bronze medal with Maxine. After high school, Cyndi balanced equine college courses while working as a travel agent and training horses on the side.
The turning point in her career came when she secured a working-student position under trainer Tracy Roenick at Dynamite Dressage. “I quit my day job and committed entirely to horses,” Cyndi said. “As a working student with Tracy, I trained Maxine up to Intermediaire I, earning our USDF Silver medal. I later leased her to young riders who earned their Bronze medal scores on her. She retired at 19 years old.”
Today, Cyndi's business has come full circle. “This is the third time in my career I’ve worked out of the same property, though it’s now under a new name, Royal T Equestrian. I worked there again when I was pregnant. Then the barn went up for sale again, and now I'm back, all these years later,” she said. “Ironically, the same manager who was managing the first time around manages now, so it feels like home.”
When naming her training business, the choice was clear: To The Max Dressage. “It was named partly in honor of Maxine and partly because of my personality: if some is good, more is better!” Cyndi joked.
That “more is better” mindset isn't just a slogan—it’s a philosophy that spills into every area of her life. “I had addiction issues when I was younger, but I have been sober for 27 years. ‘To the max’ was a big part of that, too—my nature has always been to be addictive about what I do, for better or worse. I value my sobriety and I wouldn’t have the life I have today without it.”
That intensity carries over to another hobby: running. “My preferred distance to train for is the 100-mile trail race,” Cyndi said. “It is a continuous effort without sleep, requiring steady hydration, precise hourly caloric intake and careful foot management. On a flat course, my personal best for 100 miles is 22 hours and 45 minutes; on a technical mountain course with 18,000 feet of elevation gain, my time was 35 hours and 20 minutes.”
Ultrarunning directly informs her approach to her horses’ athleticism and conditioning. “Aerobically, it enhances my stamina for riding,” Cyndi shared. “Structuring my own training blocks—incorporating build weeks, recovery phases and tapering prior to major events—provides deeper insight into conditioning my horses. Muscle development occurs during recovery, not during exertion, which shapes how I sequence my competition seasons.”
Trail running also offers a dedicated mental reset. “Running is a dedicated space where I can focus purely on the trail without managing external roles as a trainer, rider, wife or mother. It’s an endeavor I pursue entirely for personal fulfillment.”
To maintain high running mileage, her daily routine begins long before sunrise. “I wake up between 2 and 3 a.m.,” she revealed. “I complete my runs while my household is asleep, head to the barn between 6 and 7 a.m., and reserve afternoons for family.”
That early-morning discipline serves Cyndi well in her home base of Scottsdale, Arizona. Operating out of the desert requires navigating unique environmental factors, especially during the summer months. “I was born and raised here, so I’m super partial to this area—I’m a desert rat!” Cyndi said. “Unfortunately, turnout gets limited in the summer because it’s just too hot, and we don’t have grass pastures. When people relocate here or come out for the winter, they’re always like, 'It's so brown!' Our horses don't even know what to do when they see green grass. But luckily, we don't deal with a lot of skin or fungal issues here.”
Summer temperatures frequently exceed 115°F, requiring strategic management to keep horses safe and comfortable. “Summer is our hardest season; we just have to put our heads down and get through it. We utilize a covered arena with proper footing, misters and fans. The main priority is ensuring all horses are worked before the heat becomes severe.”
One of the biggest desert challenges is managing anhidrosis. “We have some horses that pop up with anhidrosis in the summer, and that can be tricky,” Cyndi said. “My very first Grand Prix horse had it and didn't sweat a drop. I would ride early and sponge him off every walk break because nobody was there to help me at 3 a.m. Now, I have a fantastic acupuncturist who works on the horses at the start of summer, and a few even get a daily beer to keep their systems sweating.”
Rather than pushing intense physical efforts during peak heat, Cyndi treats mid-summer as a maintenance phase to keep the horses fresh. Developing top-level performance horses in the Southwest also demands significant travel logistics compared to East Coast circuits. “Reaching competitions requires substantial effort,” Cyndi emphasized. “This season, we completed two local shows: three in Del Mar—a seven-hour drive each way—and one in Oregon, which was a 25-hour trip total. I drove the Oregon trip myself, monitoring Jack on the trailer camera during an 18-hour leg.”
The US Equestrian Open has provided Cyndi with a new opportunity. “The championships are only four and a half hours away from us for the next few years, which never happens! We always have to go east to Chicago, Kentucky or New Jersey.”
Managing that demanding schedule of long road trips, ultramarathon training and helping clients chase their dreams requires boundaries—because at the center of Cyndi's world is her household and parenting journey. “Like every girl, I wanted to go to the Olympics when I was younger,” Cyndi said. “I have a more realistic view now. Only three horses go every four years, but the compromises and sacrifices you have to make to do that are greater than what I might be able to do at this point in my parenting journey. My husband and our son, Ronin, whom I homeschool, are my top priorities. When I decided to become a mother 10 years into my marriage, I committed to structuring my career so I could pursue high-level athletic goals while remaining fully present at home.”
Part of maintaining that balance and peace of mind also meant changing her approach to horse ownership. “I don't own any horses anymore, other than a 13.2-hand pony my son rode when he was little,” Cyndi said. “After Maxine, I had my first Grand Prix horse until he was 29, and another young one until he was 21. Later, I bought a horse with a client and then sold my share because I realized that to really chase my dreams, I didn't have the financial backing to make that happen. I’d rather let a client own the horse and if we can do something fun together, great! If not, they have a great horse. I’m blessed to have great clients, many of whom have been with me for years.”
While the energetic freestyle at HITS Del Mar brought down the house, Jack’s success lies in one of those long-term bonds: Cyndi’s nearly quarter-century relationship with Ann Damiano. “Ann met me when I was a 20-something kid, newly married,” Cyndi said. “She came in with her off-the-track Thoroughbred and had a dream that she was going to own a fancy warmblood one day—now she owns four of them!”
“I’d describe our relationship as like sisters or an old married couple—we definitely bicker!” Ann admitted. “But above all, our partnership is collaborative. With my horse Jack, she does ride him, but I’m fully engaged in every decision, from setting our goals and picking horse shows all the way down to choosing his freestyle music. There’s that saying, ‘Don't come to me with problems, come to me with solutions,’ and that’s what she does: Cyndi just handles things, so we don't have to worry. I remember being out of town years ago when one of my horses got caught up and slashed his leg. She called me and said, ‘I just wanted to let you know he cut his leg pretty badly, but the vet is already here.’ She's always on top of everything.”
In a true partnership, Cyndi couldn’t do what she does without Ann’s support. “Ann has always been my ride-or-die,” she said. “She believes in me so hard.”
That support has extended far beyond training rides and horse shows into key milestones in Cyndi’s life. “Ann threw my baby shower, even though I got pregnant during a season where she was hoping I'd qualify her horse for a national championship!” Cyndi laughed. “I told her she was going to have to step up and take over the ride that year because I was having a baby. She didn't hesitate; she immediately said, ‘OK, I’ll learn to ride him better.’ It’s a very special relationship. People in this industry are not often blessed to have clients stick it out with them for this length of time.”
“Cyndi is one of the hardest-working trainers out there, and what I love about her is that she's always willing to learn,” Ann said. “Whenever she gets the opportunity to ride with another trainer, it’s all about asking, ‘What new tool can I add to my toolkit?’ The better she gets, the more it benefits all of us as her clients.”
To refine her riding skills, Cyndi takes lessons with Nick Wagman, whose coaching style complements her extensive experience. “Working with Nick has been valuable for both me and my clients,” Cyndi said. “He is an exceptionally capable clinician who engages enthusiastically with adult amateurs while offering structured, high-level instruction. At this stage in my career, I benefit most from a collaborative coaching dynamic where we discuss feel, observation and training strategies together.”
That collaborative coaching clearly paid off at the FEI North American Youth Dressage Championships (NAYC) this summer, where Cyndi coached one of her young riders, Nicola, to a strong finish: 9th in the team test, advancing through the individual test to reach the freestyle, and placing 11th in the freestyle. In August, Cyndi and Nicola attended the Festival of Champions in Chicago, where Nicola finished fifth nationally and Cyndi placed third in the Markel/USEF 7-Year-Old Dressage National Championship aboard Online H, owned by Rebecca Bruening. Next, Cyndi has her sights on the Open in November.
True to her program’s name, Cyndi is living life To The Max.
Follow Cyndi on Instagram @tothemaxdressage or visit tothemaxdressage.com
Photos by Kirsten Ziegler, kirstenziegler.com or Instagram @kirstenzieglerphoto
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