The small bay mare had spent years weaving through the turns at Woodbine Racetrack with the determination of a horse twice her size, but even in retirement, Cheeky Pint still commands attention wherever she goes.

At first glance, many are struck by how slight she appears. Then comes the second impression — the unmistakable presence, intelligence and spark that have defined her throughout her life around horses.

Cheeky Pint retirement story

For Norma MacDonald, the mare’s new owner and partner, that charisma was impossible to ignore from the very first meeting at LongRun Thoroughbred Retirement Society in Hillsburgh, Ontario.

“She turns heads everywhere she goes,” MacDonald said. “Every time someone sees her, they remark how much smaller she is than they imagined. She has a tiny frame, but a huge personality.”

The daughter of Society’s Chairman out of Kipling’s Joy built a respectable career on the track despite competing largely in claiming company. Across 26 starts, she compiled seven wins, six seconds and five thirds while earning $144,489 in prize money.

Bred in Ontario by Janeane Everatt, James Everatt and Arika Everatt-Meeuse, Cheeky Pint was purchased for $15,000 at the 2018 Keeneland September Yearling Sale before joining the barn of Don MacRae at Woodbine.

MacRae recalled first spotting the filly from afar at the Kentucky sale.

“She reminded us of another filly we had trained and she just had a great look about her,” he said. “From day one, she was a sweetheart. She wasn’t the biggest horse in the barn, but she always gave everything she had.”That toughness quickly became her trademark.

After finishing third on debut in October 2019, Cheeky Pint broke her maiden the following summer with an emphatic 3¾-length victory over Woodbine’s inner turf course. Between October 2020 and August 2021, she reeled off four consecutive victories, showing a particular fondness for the tighter turf turns.MacRae believes her compact frame worked to her advantage.

“She would just zip around those turns and punch for home,” he said.Her final race came at Woodbine in October 2023, where she finished third before being retired sound and donated by MacRae and Keowee Racing to LongRun Thoroughbred Retirement Society.

The move would eventually change MacDonald’s life as much as it changed the mare’s.Having previously retrained several former racehorses, MacDonald visited LongRun shortly after taking time away from horses following the birth of her second daughter. She arrived hoping to find another Thoroughbred to restart.

Cheeky Pint immediately stood apart.“I saved Cheeky for last because I knew I would fall in love with her,” MacDonald recalled. “There was so much intelligence in her eye. I rode her and she answered every question correctly. I didn’t ask much from her that first ride, but it told me everything.”

During the adoption process, MacDonald received heartbreaking news that her best friend was nearing the end of her life. Before rushing to her bedside, she shared photos and videos of Cheeky Pint.

“She told me I had to get this horse,” MacDonald said. “I lost her a couple of weeks later, so those words have always stayed with me.”The thorough vetting process carried out by LongRun only strengthened her admiration for the organisation.

“They inspected everything carefully,” she said. “They wanted to know exactly where the horse was going and how she would be cared for. It showed how much they value these horses after racing.”

Once settled into her new surroundings, Cheeky Pint began adapting to life away from the racetrack and towards a new discipline — show jumping and eventing.The transition was gradual.

“It took time because she was so good at racing,” MacDonald explained. “At first, she didn’t really understand this new world. We worked slowly on basics and building confidence.”Before long, the mare’s natural athleticism emerged once again.

MacDonald now trains with coach Jenna Belanger and has already enjoyed success with Cheeky Pint in hunter and jumper competition, including strong performances in the 0.90m division during her second show season.

“The higher the jumps, the bolder she becomes,” MacDonald said with a laugh. “She absolutely loves it.”The pair have also ventured into cross-country schooling, where the mare’s fearless attitude has continued to impress.“She’ll tackle water, ditches, brush — anything you ask. Then she looks for the next challenge straight away.”

The bond between horse and rider has become evident to everyone around them.“People always comment on how connected we are,” MacDonald said. “Over these two years, we’ve really found our rhythm together.”Cheeky Pint’s retirement story has also highlighted the growing importance of aftercare programmes for former racehorses, with LongRun continuing to provide second opportunities for retired runners across Ontario.

MacDonald remains deeply appreciative of the support she received throughout the adoption process and beyond.“If I had all the money in the world,” she said, smiling, “I would adopt every horse LongRun has.”

Now nine years old, Cheeky Pint appears to be thriving in her second career just as much as she once did on the turf.And for all the victories she collected during racing, her greatest success may simply be the life she has found afterward.“She retired sound from racing and we’re so happy she’s living her best life,” MacRae said.

For more stories, results, and updates from the world of horse racing, stay tuned to racebuzz