Canada’s ‘Keepmeinmind’ eyeing massive upset at Kentucky Derby

One of the biggest upsets in horse racing history took place in 2009 when Mine That Bird (50-1) won the Kentucky Derby. That thoroughbred’s career began at Woodbine Racetrack in Toronto.

Twelve years later, a Canadian-born trainer and owner hope to pull off another massive upset in the annual Run for the Roses.

Robertino Diodoro, originally from Calgary, is one of North America’s leading trainers. His first-ever appearance in the opening leg of the Triple Crown this Saturday at Churchill Downs is with ‘Keepmeinmind’. The three-year-old colt is co-owned by Whiterock, B.C. native Arnold Bennewith.

“It’s every trainer’s dream to have a horse running in the Kentucky Derby,” Diodoro said from Louisville, K.Y., earlier this week. “I don’t even know how to put it in words to be honest. And to be here with Arnie… whose son Lance coached me in hockey when I was 12 years old… it’s pretty special.”

The journey Diodoro has taken to get to the 147th Kentucky Derby is unlike many of his colleagues in the horse racing industry. Growing up in western Canada, Diodoro was a hockey goalie. He played junior-A in the now-defunct Rocky Mountain Junior League in B.C. with the Williams Lake Mustangs. When his hockey career didn’t pan out, he got involved with thoroughbreds, something both of his parents’ families were involved in.

“I guess you could say I was an ‘early bloomer’ in hockey,” chuckled Diodoro, who now calls Hot Springs, Ark., home. “My mom’s side of the family was into horse racing, as was my dad. I was going to the track all the time. When I was 16 and should have gotten more serious about hockey, I got more serious about horse racing. When it’s in your blood, it’s hard to get out.”

There’s no question Diodoro made the right decision and his hard work has certainly paid off the last few years. Since the start of 2020, Diodoro’s stable of horses have been entered into just under 1,400 races around North America. Those horses have earned just north of $6.3 million (US). Of those entries, 23 per cent have been winners, including ‘Keepmeinmind,’ who captured the Kentucky Jockey Club Stakes last November at Churchill Downs

“Things have really come together the past few years,” adds Diodoro, “I’ve been really blessed to have some new owners come into the barn, plus we have a lot of guys who’ve been with us a long time and stuck with us. It really is an honour to be here.”

The first time Diodoro trained a horse that won a race was August 2, 1995 when ‘Manchu Prince’ found the winner’s circle at Northlands Park in Edmonton. The prize purse that day was $5,811. Since that day, Diodoro’s career earnings have surpassed $48 million (US), which includes capturing the Canadian Derby three times (2013: ‘Broadway Empire’, 2014: ‘Edison’ and 2018: ‘Sky Promise’).

Any horse trainer who has won that much money is obviously good at what they do. But training winning horses also requires luck. A lot of luck. Diodoro’s first appearance at the Kentucky Derby is considered by many to be very lucky, as 15 other horses who had more Derby qualifying points than ‘Keepmeinmind’ elected to bypass the race for three-year old thoroughbreds.

“He had a big two-year-old year, but he’s had some excuses for a tough start this year,” explains Diodoro, who trains many of his horses at Oaklawn Park in Arkansas. “The track was closed down for two weeks due to a snowstorm. We’ve made a few changes for him for this Saturday, including taking blinkers off him (for the first time). We’re more than happy he’s in the No. 4 post. We’ll see what he can do.”

In six career starts, ‘Keepmeinmind’ has a first, two second and one third-place finish. He is one of six horses in the 20-horse Derby field listed at 50-1 morning line odds. By comparison, the early favourite for the $3 million (US) race is the undefeated ‘Essential Quality’ (2-1).

Diodoro and Bennewith have also teamed up with another horse entered in a lead-up race to the Derby on Saturday. ‘Dreamer’s Disease’ is scheduled to run the $1 million (US) Pat Day Mile. Diodoro also has a long-shot filly ‘Ava’s Grace’ running in Friday’s $1.25 million (US) Kentucky Oaks.


• Diodoro is just the third Canadian-born trainer to have a horse entered in the Kentucky Derby. Lucien Lauren (Joilette, Que.) trained Triple Crown champion ‘Secretariat’ in 1973 while David Cross Jr. (Vancouver) trained ‘Sunny’s Halo’ to a first-place finish in 1983

• Bennewith tries to join an exclusive club of Canadian-born owners who had Derby-winning colts. Among them:

-Frank McMahon (for whom Calgary’s CFL stadium is named after) was born in Moyie, B.C., and owned 1969 Derby winner ‘Majestic Prince’

– Winfield Farms (Oshawa, Ont.,) became Canada’s first Derby winner when they owned ‘Northern Dancer’ in 1969

– David “Pud” Foster (Toronto) owned ‘Sunny’s Halo’ in 1983

– Paul Reddam (Windsor, Ont.,) owned two Derby champions (2016: ‘Nyquist’ and 2012: ‘I’ll Have Another’)

• The last horse to win the Kentucky Derby and go on to win the Triple Crown was “Justify” in 2018. John Gunther (Langley, B.C.,) was the breeder of Justify. Gunther owns ‘She’s Got You’, set to run in Saturday’s $500,000 Churchill Distaff Mile.

• Florida Panthers owner Vinny Viola has ownership in two horses running in this year’s Kentucky Derby. He is the primary owner of ‘Known Agenda’ and co-owner of ‘Dynamic One’

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