It took but one trip to the racetrack, a pair of two-dollar wagers, and a tidy profit to put Charles Overland on the path to a long-term life as a thoroughbred owner.
As he peered out the window of the taxi that was taking him to Woodbine Racetrack, the young articling student became more and more curious about the place he had heard of, but had never been to.
“I was put in a cab and sent off to the Jockey Club of Canada to get a prospectus signed,” recalled Overland. “I had never been to Woodbine before. When I walked in, I met a gentleman named Al Isbister, who then tells me it will be about half an hour before I can meet with the board of directors.”
Rather than the tedium of having him sit around and wait, Isbister had a suggestion for Overland: head down to the main floor and make a wager.
There was only problem Overland had with that option.
“I remember looking straight at him after he told me to go bet a race, and said, ‘Okay. So how do I do that?’”
After some informal instruction, Overland took what he learned, program in hand, and trekked downstairs minutes before the seventh race was ready to get out of the gates.
He understood the basics of making a two-dollar win bet, but now had to figure out which horse to select for his modest investment.
“I was born in the village of Erin and there was a horse in the seventh called Village Squire,” remembered Overland. “Call it a hunch, I guess. Here I am, making $30 a week, not really knowing what I’m doing, but I decided that was the horse I was going to bet on. And don’t you know it? The horse wins and pays $30.”
Overland was less-than-subtle when he admittedly skipped back upstairs to see if the board was ready for him.
“I suppose I must have bounced in there because a man by the name of Elgin Armstrong took one look at me and pretty much figured out what happened,” said Overland. “It turns out, he had a horse running in the next race, Admiral Armbro, who he thought had a big shot to win. Down I went again, bet another two dollars, and watched the race. Admiral Armbro wins and pays $25. So, in less than an hour, having never been to the racetrack, I bet four dollars and walked out with $55. That’s how it all started for me.”
A few years later, Overland and close friend, fellow law school student, Bob Heather, decided to get into the ownership side of thoroughbred racing, shelling out a small sum for their first horse.
It marked the beginning of Overheath Stables – a play on their last names – and an enduring love for the sport of kings.
“We’ve always bought one at the Yearling Sale each September,” noted Overland. “It was just the two of us, but we expanded over the years. We have anywhere between 16-20 people involved. Bob passed away this year, but we’ll always race under that name.”
There have been numerous memorable moments and runners over the years for Overheath, including the talented trio of Pete’s Fancy, Questing Knight and Festive Knight.
A daughter of champion Peteski, Canadian Triple Crown champion and the country’s Horse of the Year in 1993, Pete’s Fancy won 10 of 40 starts, taking three of eight starts in 2000.
“She was funny,” offered Overland. “Initially, she couldn’t get out of her own way, but then she put it all together and had a solid career.”
Questing Knight, a son of Ascot Knight, made 11 trips to the winner’s circle and finished in the top three in half of his 48 lifetime starts. He was named Woodbine’s claimer of the year in 2004.
It was multiple stakes winner Festive Knight, also a son of Ascot Knight, who delivered Overheath its biggest thrill ride to date.
Trained by Mike De Paulo, the bay finished third in the 1998 Coronation Futurity Stakes, a key race on the road to the Queen’s Plate, won the Kingarvie Stakes that same year, and the Halton Stakes in 1999.
Festive Knight, selected as the second choice in the Queen’s Plate Winter Book, finished fifth to Woodcarver in the 1999 ‘Gallop for the Guineas.’
The horse’s path to the Plate was televised nationally on CBC in the Sovereign Award-winning documentary, Maiden Dreams.
“It was amazing to be part of that,” recalled Overland. “Just the lead up to the big race, all the excitement and pageantry involved in it – you don’t ever forget that.”
The stable’s number of horses, like the man himself, remains modest. Currently, Overheath owns less than three, to be exact.
“Right now, we own 2 ¼ horses,” said Overland with a laugh. “We own two of them outright and we have a quarter share of another with three other people.”
Overland keeps his co-owners up to date on the Overheath horses via email through what he’s dubbed ‘Report to Investors,’ which in lean years his partners renamed, ‘Report to Donors.’
And while the operation has a fraction of the horses that many of their contemporaries boast, the longtime owner remains committed to the sport and proud of Overheath’s longstanding presence.
“The fun of it is certainly seeing the horses, the competition,” said Overland, who is retired from practicing law after 40 years in the profession. “But, the joy of it is also the people you meet. Just standing at the rail in the mornings, sharing stories – that’s a wonderful part of it. Bob and I were lucky enough to have (Canadian Horse Racing Hall of Fame inductee, owner and breeder) Mel Lawson as a mentor when we first starting out. If you had any questions, he’d happily answer every one. That help was invaluable.”
“I remember (Canadian racing legend and hall of famer) Bud Willmot would say that horseracing is a great thing for retirees to get involved in,” he continued. “I think a yearling investment compels a focus on the future. It’s like they say - you’re not old as long as you have a young horse.”
Which is why Overland, a man instrumental in the formation of thoroughbred syndicates, still feels very much like the young kid who walked wide-eyed through the doors of Woodbine many years ago.
“It all began with those two bets,” he said. “I didn’t know what to expect that day. But, it certainly turned into something I’m very grateful for.”
Story by Chris Lomon
(C) Ontario Racing 2017. All rights reserved. May not be reproduced without permission.
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