Remembering Longtime Horseman Tommy O’Keefe

Like many others, Steve Roberts will remember longtime horseman Tommy O’Keefe for more than just his time as a multiple graded stakes winning trainer.

A lifetime winner of 245 races, 13 of them stakes, with over $6 million in career purse earnings, O’Keefe passed away on December 22nd after a courageous battle with bone cancer.

“Tommy was a great horse person who truly loved the game,” said Roberts, himself a long-time racing participant, who is currently a jockey agent working out of Woodbine. “In the days since he passed, I’ve heard so many great stories about Tommy from other trainers and horse people. He had the respect of so many people.”

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Born in Waterford, Ireland, in 1941, O’Keefe would eventually land in Canada. After a short attempt at becoming a jockey – he was too heavy to make weight – in his homeland, he found a treasured life in horse racing at Woodbine.

He galloped several high-profile horses, a list that includes Kennedy Road, a Canadian champion with a fearsome reputation in the mornings and afternoons.

“Tommy told me that he would work the ones that were bad actors,” said Roberts. “I wasn’t around during his galloping days, but it’s something he enjoyed and did until he was around 60.”

Roberts would, however, get to know O’Keefe well. The friendship developed through Roberts’ father, Les, a Thoroughbred owner who raced under the name Wings of Erin Farm, after the property he owned northwest of Woodbine.

“My dad bought that farm in 1998 and Tommy moved into the cottage that was there. I had quit my job and moved into the house a year later, to help after my stepmother Helen had passed away from pancreatic cancer. I had known Tommy since 1983 when he started training horses for my dad, but living there allowed us the chance to get to know one another better. I was helping turn out the horses and mucking the stalls, so it was a time where I got to hear lots of stories from Tommy – he had a lot of them.”

O’Keefe also had several standout horses who flourished under his watchful eye.

Some of his top performers include graded stakes winner Mulrainy, four-time stakes winner Wings of Erin, four-time stakes winner Inspired Kiss, and two-time stakes winner Masada. He won the 1978 Niagara Handicap (G3) with Tuxedo Mac.

“We tried our hand at breeding with mixed results,” said Roberts. “We did have a nice mare, Foxy Fiddler, who threw all winners. She produced Foxy Jean, Taranaki, Fiddler’s Green, and Curve of the Moon. We had a small farm operation compared to most, but we had a great run. In 2011, my father sold the farm and got out of the business. Over the last 12 years, Tommy trained a few of his own.”

O’Keefe’s adoration for the sport would have made him a natural in other roles, noted Roberts.

“I had told Tommy that he should become a bloodstock agent because he had such a keen eye in buying yearlings. He loved the sales. Every year, he’d buy that one diamond in the rough and turn it into a multiple winner. He enjoyed matching young stallions with first or second foal mares.”

O’Keefe’s top season, by wins, was 13, which he reached in 1976 and 1999. His top season, by earnings, was in 2002 when his starters totalled $560,994.

On September 16, 2012, champion rider Emma-Jayne Wilson guided D’Wildcat Gold, a horse trained and owned by O’Keefe, to victory in the afternoon’s race. It was the 1,000th win of Wilson’s career.

His last training win came on July 1, 2022, with Ingordwetrust, a son of Flashback-Messageinabottle he also owned. He recorded 16 career wins as a sole owner.

“Tommy continued to train one or two horses every year, right up until this past spring,” said Roberts. “I’d always pass by his barn and talk horses and soccer, something we both enjoy. He was in a lot of pain the last few years, but he would be at the barn each day and leading his horses to the track to train.”

Roberts has an abundance of happy recollections of O’Keefe, including the bond he shared with his father.

“My dad and Tommy were great friends. They both loved English football. Tommy supported Manchester United, and my dad supported Liverpool, which led to many debates at the local pubs when they would watch matches with other friends.

“Tommy was very upset when he heard that my dad passed away suddenly in October 2022. Even though Tommy was quite ill at the time, he still came to his celebration of life and raised a few jars. They both had a great run.”

Roberts was grateful to have a trackside view to see most of their shared successes.

“One of my fondest memories was watching Tommy develop the horses and then seeing the success he would have for my dad. Seeing the horses start at our farm and then seeing them go on to be in the winner’s circle will always be special. Tommy had a big impact on a lot of people’s lives.”

That list would extend beyond the racing world.

When Les Roberts sold Wings of Erin, the new owners were happy to let O’Keefe maintain his residence there.

“Nadia, the woman who bought the farm from us, made sure Tommy was taken care of. He lived in the same cottage when my father owned it, and she was kind enough to allow him to continue to stay there. Over those 10 years, they got to know and love Tommy, seeing him as a grandfather figure. She did so much for him. He made his final arrangements through her.”

There are plans for a memorial service in January. Details will be announced once a date and time are set.

Roberts expects to see a large outpouring of support from the Woodbine racing community.

“He was a very good horseman, who was well thought of. He taught me a lot. I watched and learned a lot from Tommy. It’s been great to hear horse people and others talk about him. You hear those stories, and you realize just how much he will be missed around the racetrack.”