Cheeky Pint: The Tiny Thoroughbred Winning Hearts in Her Second Career

The diminutive Thoroughbred mare rarely goes unnoticed.

Far more often than not, Cheeky Pint, a daughter of Society’s Chairman out of the Kipling mare Kipling’s Joy, draws widespread attention before and after she steps into competition.

It’s a scene that never fails to bring out an appreciative smile in Norma MacDonald.

“She turns heads everywhere she goes,” said MacDonald, a longtime equestrian. “Every time someone sees her, they will remark, ‘She is so much smaller than I thought she would be.’ She has a very tiny frame, but a big presence.”

While she lacks size, the 9-year-old mare is chock-full of personality, a winning blend of intelligence, slight irreverence and unmistakable alacrity.

Cheeky Pint used those very characteristics to great effect throughout a prosperous racing career. ​

Over 26 starts, the majority coming in the claiming ranks, she produced a 7-6-5 mark, accompanied by $144,489 in purse earnings.

Bred in Ontario by Janeane Everatt, James Everatt and Arika Everatt-Meeuse, Cheeky Pint was a modest $15,000 purchase at the 2018 Keeneland Association September Yearling Sale.

Trained and co-owned by Woodbine-based Don MacRae, she produced a third in her first career start, on Oct. 2, 2019, before breaking her maiden in fourth race, a 3 ¾-length score at 1 1/16 miles over the Woodbine inner turf, on July 4, 2020.

From Oct. 18, 2020, to Aug. 17, 2021, Cheeky Pint won four straight races. Her final race on Oct. 19, 2023, at Woodbine, yielded a third.

Not long after that last engagement, MacRae and co-owner Keowee Racing donated Cheeky Pint to LongRun Thoroughbred Retirement Society, the respected horse retirement and adoption organization established in 1999.

She took up residence at LongRun’s farm, joining dozens of other former racehorses on the picturesque and pristine 100-acre property nestled in Hillsburgh, Ontario.

“Cheeky Pint was a filly that my wife and I saw from a distance down at the sale in Kentucky. She had the Ontario-sired sticker on her hip, so we decided to go over and have a look at her,” said MacRae, a multiple graded stakes winner, who has recorded 617 career wins. “She reminded us of a filly we trained called Post to Post and had a great look to her, so we took a shot on her and bought her to bring home to Canada.

“From day one, she was always a sweetheart and a joy to be around. Although she wasn’t the biggest filly in the barn, it didn’t stop her from throwing it down and trying her all in every start for us. Her size made her an avid lover of the (Woodbine) inner turf. She would just zip around those turns and punch for home.’

Just over two years ago, MacDonald, who lives with her family on a small horse farm just outside of Shelburne, Ont., found herself at LongRun, hopeful of finding a horse to bring into her life.

“In my lifetime, I have bought, trained and sold many Thoroughbreds, to give them a second chance at a new career. I had just had a baby, so I took a bit of a break before and after I had my second daughter.

“After a time, I went to LongRun, which was highly recommended by my friend Laura Bishop, who has adopted quite a few mares from them. She said, ‘The next horse you get has to come from LongRun.’ So, I decided to go that route for the first time.”

It would be a worthwhile endeavour.

MacDonald looked at three horses that day in Hillsburgh, Ont. One, in particular, drew her in.

“I looked at two other horses when I was there, and I saved Cheeky for last. I knew I would fall in love with her. I saw her in the stall and there was so much intelligence in her eye, and it struck me then that this horse has a big future in front of her. I rode her and she just answered my questions correctly. I didn’t ask a lot from her on that first ride, but it told me so much.”

In between filling out adoption papers, MacDonald received some devastating news.

“My best friend, who had been cheering me on in everything I did in equestrian and my life, was going to pass away. Her son called to let me know. It was very emotional for me, so after I got the call, I raced to her side and told her about Cheeky. I shared all the videos and photos I had. She told me that I had to get this horse.”

“I lost her a couple of weeks later, but her words and what she saw in Cheeky meant the world to me.”

Not long after that tearful farewell, MacDonald received an email from LongRun with a request to visit her farm.

She gladly obliged.

“I love that they scrutinize where the horses are going. They came to my farm and heavily evaluated the safety and the care the horse would be coming into. I love that it was a long interview process. They did not make a quick decision, and it made me feel that they put a lot of care into placement. They didn’t just take my word. They wanted to make sure everything was right for this horse.”

LongRun agreed that it was.

Cheeky Pint was now in the care of MacDonald.

After letting her acclimate to the new surroundings, MacDonald slowly began to introduce Cheeky Pint to a new pursuit.

“It took a while for her to transition into the world of jumping because she was so good at what she did on the racetrack. It took her time to understand what this world was all about. I just started working on basics, building the foundation and education for her new calling. 3-Day Eventing is my favourite equestrian discipline. My hope is to take her into that world.”

A realm that MacDonald discovered was tailor-made for the mare with a seemingly endless amount of curiosity and try.

“She requires respect. You can’t tell her what to do – it needs to be an ask, as opposed to an order. Once she trusts you, she will give you everything. She will test you, but it is her way of confirming you are someone worthy of her partnership.

“She is also very keen and quite forward. I have a hot seat, so I have to check myself and take a deep breath before I get in the saddle. She feels energy very readily, which is great, because in the Jumper world, you want that response. If I ask a little of her, she will give a lot.”

Over the past two years, the pair has shared countless treasured moments.

“I have been training her to jump and she is a machine. She just loves it. I have been working with coach Jenna Belanger, who has been very instrumental in supporting our growth and bringing us to the Silver Series Hunter and Jumper rings. We kicked off her second show season a few weeks ago and shone in the .90m division. The higher the jumps, the bolder she performs.”

By now a familiar tradition, Cheeky Pint, who now boards just a few minutes down the road from MacDonald, has remained a crowd favourite among fans, participants, and attendees.

MacDonald never tires of the outpouring of affection for her beloved mare.

“Anyone who meets this horse can immediately sense the kindness in her. She has a way of making people smile the moment they approach her. Though she’s not one to seek constant affection, her big heart shines through in everything she does. Over the two years I’ve spent with her, I’ve come to appreciate the extraordinary depth of her character. She’s analytical, intelligent and very curious. And with that intelligence comes some mischief, which makes her name, Cheeky, especially fitting.”

They also see the bond between rider and horse.

“Everyone sees that, just how connected we are. They are so impressed and happy to see the partnership we have. Over the last two years, we have found our groove, where I understand her and she understands me. There is not a lot of friction. If her body can do it, she will give me her all and then some.”

MacDonald is grateful for her experience with LongRun.

“I love LongRun. During the adoption process, there were mandatory vet checks and 6 and 12 months, to make sure the health of the horse was optimal. They had their Graduate Show last fall, and they moved mountains for us. I had no transportation, but LongRun figured out a way to get Cheeky there. So, we had the red carpet rolled out for us. It feels like I am part of this family.”

She added with a laugh, “They have been wonderful. If I had all the money in the world, I would adopt every horse LongRun has.”

MacDonald still feels she has hit the equine jackpot.

“Long term, I hope to do a few more years of competition with Cheeky. I believe she could be a very solid upper-level Show Jumper or Event horse. I took her cross-country schooling a few times. She just gallops through anything I ask of her – ditches, water, brush, whatever it is. And she just looks at it like, ‘Okay, what is next?’ She is so excited that sometimes I have a tough time holding her back.”

“I am really excited to see where she will take us.”

Wherever the next jump leads, Cheeky Pint has shown that sometimes the smallest horses leave the biggest imprint.

“She retired sound from her racing career and we are so happy she is living her best life,” said MacRae.

Chris Lomon, Woodbine