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Chelsey O’Brien

Chelsey O’Brien Profile Photo

Horse trainer

Chelsey O’Brien is a self professed OTTB lover. She started riding at the age of 5 in Massachusetts and grew up as the guinea pig/crash test dummy for all kinds of horses primarily in the hunter jumper realm. As a teen, she helped to restart dozens of OTTBs and helped and boarded at a farm that did layups, rehabs, restarts and resales where she learned about the bigger aspects of horses, not just riding. This led to purchasing her own project at 16 to bring along alone that further cemented her love and devotion to the thoroughbred.

After a bad riding accident causing serious concussion during an IHSA show in college that left doctors telling her she should never ride again, Chelsey took time off only to find a life without horses was not one for her. What better way to come back into a year off of riding by going to Suffolk downs and buying one three days off the races? This horse, who was purchased for what looked like a fabulous conformation for the hunters, quickly showed her ineptitude for that discipline which had Chelsey seeking to get creative to find what set her mare’s heart on fire. By chance, she tried barrel racing and that was the ticket.

While training this horse for barrel racing, Chelsey also worked at a thoroughbred breeding farm in Southern Indiana, where she furthered her education of proper husbandry, foaling, handling, and large scale operations while helping with over 100 mares in foal, foals, weanlings, yearlings, in the breeding shed and daily care. She headed home to New England with that experience and a few more OTTBs and started teaching and training again, while also working at show farms as a groom, rider, trainer, and manager. Her career brought her down to Wellington FL, where she and her family resided for 2 years but another riding accident after having her daughter brought them up to Northern Virginia.

She took a job as a broodmare manager at a private farm where she foaled 25 mares over 2 years. During that time she found homes for many retiring racehorses from the farm, prepped sales yearlings for Saratoga, Keeneland and Timonium, cared for layups and handled surgical rehabs. This job was a great test of the many years of horsemanship/husbandry education Chelsey had gotten from previous jobs and horse people she was mentored by.

In 2023, she was chosen to be one of the inaugural trainers for Pastured Place, a not for profit out of Pennsylvania dedicated to Thoroughbred Aftercare. They sponsored her for the last two years to compete with two of their horses at The Retired Racehorse Project Thoroughbred Makeover, where this past season, Chelsey and Unbeknownst To Me were second overall in the Barrel racing and ninth in the ranch work. She now manages a farm in Berryville VA where she offers training, restarts, rehabs, lessons, and sales. Her business focuses on a horsecentric approach to finding what the horse wants to do, whether that be an English or western discipline.

This year, Chelsey is gearing up for another journey to the RRP. This years hopefuls include Pastured Place horse, The Pepsodent Show aka Peppy, and a personal horse named Fuzzy Wuzzy aka Fuzzy. Chelsey hopes to show the versatility of the TB in both English and western disciplines this year.

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April 9, 2026

S3 E6: Not Just the Highlight Reel: Chelsey O’Brien on Training a Stakes-Winning OTTB and Going Viral (Part 2)

In Part 2 with returning guest Chelsey O’Brien, we catch up on what life looks like after the Retired Racehorse Project and what she’s working on next. Chelsey introduces her 2026 prospect, Rustler, aka Rusty, a stakes-winning OTTB owned by Pastured Place. He’s a very different ride from the horses she’s brought along for the Makeover in previous years, and this one is pushing her in new ways as a trainer. We talk about what that process actually looks like day to day, including the moments t...
5
April 2, 2026

S3 E5: Putting the Horse First: Chelsey O’Brien’s RRP Makeover Story and Lessons in Horsemanship (Part 1)

Chelsey O’Brien returns to OTTB on Tap for a long-awaited catch-up, and this one starts with the real story behind her 2025 Retired Racehorse Project Makeover experience. Chelsey, a Northern Virginia trainer who rides for Pastured Place, is known for restarting off-track Thoroughbreds across multiple disciplines. In this episode, she walks us through what it actually takes to bring not one, but two OTTBs to the RRP. From hunters and Western dressage to barrels and ranch work, she shares how s...
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Sept. 4, 2025

S2 E34 | Double the OTTBs, Double the Disciplines: Chelsey O’Brien’s Journey with Peppy & Fuzzy | RRP Trainer Chronicles

In this installment of RRP Trainer Chronicles, an OTTB on Tap Original Series, we catch up with returning trainer Chelsey O’Brien as her 2025 RRP Makeover journey takes shape. This year, Chelsey is retraining two very different OTTBs—each with their own story and style. ✨ Peppy (JC name: The Pepsodent Show) has stepped into the hunter ring, showing the elegance Thoroughbreds can bring to the discipline. His second Makeover division is still undecided, but one thing is certain—he’ll be availab...
29
June 26, 2025

S2 E29: A Tale of Two OTTBs: Chelsey O’Brien on Confidence, Giving Back & RRP Dreams

Virginia-based trainer Chelsey O’Brien returns to OTTB on Tap as she gears up for the 2025 Retired Racehorse Project Thoroughbred Makeover—this time with two OTTBs and twice the determination. Representing the nonprofit Pastured Place, Chelsey introduces us to The Pepsodent Show (“Peppy”), a charismatic 5-year-old gelding by VE Day. With a name that throws it back to the golden age of radio—The Pepsodent Show was a wildly popular 1930s–40s comedy series hosted by Bob Hope, not unlike today’s pod...
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May 15, 2025

S2 E23: Get to Know Our 2025 RRP Makeover Trainers and Their OTTBs

Meet the 2025 Retired Racehorse Makeover trainers we'll be following all season long! In this special kickoff episode of OTTB on Tap's original series, RRP Trainer Chronicles, we introduce you to four standout horsewomen—each with a different background, training philosophy, and off-track Thoroughbred (OTTB) partner. You'll get a first look at their plans for the 2025 RRP, how they came to love OTTBs, and the unique paths that brought them to this moment. Our featured trainers include: St...
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Jan. 9, 2025

S2 E9: Chelsey O’Brien’s RRP Application Tips, UBie Updates & Advice for Niamh’s OTTB Journey

In this latest episode of OTTB on Tap, we welcome back Chelsey O’Brien, a fan-favorite trainer from our RRP Trainer Chronicles. Chelsey catches us up on her post-Makeover adventures with her OTTB, UBie, and offers expert advice for navigating the 2025 Retired Racehorse Project Thoroughbred Makeover application process. As Niamh gears up to take her OTTB, Go Green, to the Makeover, Chelsey shares her insider tips for crafting a compelling application, creating a standout video submission, and ...
43
Oct. 17, 2024

Ep 43: OTTB Evaluations and RRP Makeover Recap! Plus: Maryland 5 Star Preview, Listener Spotlights, and more!

Join us for a packed episode of OTTB on Tap! We reflecting on our first OTTB On Tap Evaluates episode, sharing updates from the owners on listener-submitted horses like Baybuilt, Floo Powder, and Dragon Moon. Were we right in our evaluations? Find out in today's episode! Also, hear from our amazing listeners as we give shout-outs and share feedback about their OTTB journeys. Interested in submitting your horse to be evaluated in an upcoming episode? Fill out our OTTB on Tap Evaluation Form to...
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Sept. 17, 2024

Ep 39: Creating Value in the Undervalued OTTB: Chelsey O’Brien & UBie Finalize their RRP Makeover Prep!

In this episode of OTTB on Tap, we catch up with RRP Trainer Chelsey O’Brien as she prepares off-track Thoroughbred, Unbeknownst To Me (UBie), for the 2024 Retired Racehorse Project Makeover. UBie is owned by Pastured Place, a 501(c)(3) nonprofit serving the needs of Thoroughbreds. Chelsey shares insights into UBie’s training for Western disciplines, including barrel racing and ranch work, emphasizing the importance of "creating value in the undervalued" OTTBs like him. She also discusses the ch...
25
June 4, 2024

Ep 25: Uncovering those 'Diamond in the Rough' OTTBs with Chelsey O'Brien

Join us for another installment of our OTTB on Tap - Retired Racehorse collaboration! In this episode, we chat with Virginia-based trainer, Chelsey O’Brien, about her 2024 RRP Makeover horse, Unbeknownst to Me, or “UBie” as he is known in the barn. UBie raced 15 times and earned a little over $71,000 as a racehorse. He’s owned and sponsored for the RRP Makeover by Pastured Place, a 501(c)(3) providing retirement, rehabilitation, retraining, and rehoming to Thoroughbreds. In this episode, Chel...
14
March 12, 2024

Ep 14: RRP Trainer Chronicles: Where the Journey to Greatness Begins

Episode 14 of OTTB on Tap is out now, and we're thrilled to introduce our latest series: "OTTB on Tap: RRP Trainer Chronicles – Where the Journey to Greatness Begins." In this episode, we're diving into the world of the Retired Racehorse Project Makeover 2024! Get ready to meet our four exceptional OTTB trainers: Annika Greaney-Stanger, Julianne Pangal, Chelsey O'Brien, and Lauren Garrett-Bond. Each trainer brings their unique expertise to the table as they prepare their OTTBs for the ultimat...
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