Canadian Trainer Bennett Hoping Rascal Keeps Winning

A strong performance by local hopeful Naughty Rascal in Saturday’s $250,000, mile-and-a-sixteenth Sam F. Davis Stakes for three-year-olds at Tampa Bay Downs could result in the colt advancing to the track’s annual showcase event, the Grade III, $400,000 Lambholm South Tampa Bay Derby on March 8.

That scenario would move his trainer, 80-year-old Oldsmar oval legend Gerald Bennett, one step closer to a cherished dream.

“That (winning the Lambholm South Tampa Bay Derby) is my goal every year,” said Bennett, who won eight consecutive Tampa Bay Downs training titles from 2015-16 through 2022-23 and has nine overall, tied with Jamie Ness for the most in track history.

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“When you race at Tampa, that’s like your Kentucky Derby.”

Bennett, a Springhill, Nova Scotia, native, began his training career in Canada in 1976 saddling horses alongside Frank Merrill, who passed away in 1990.

“Frankie Merrill was big in the claiming game. When you’re young starting out, you said, ‘I’m going to be like Merrill,’” said Bennett, who ranks 13th on the all-time North America races-won list.

Bennett has saddled 4,182 winners in his 49-year career with Thoroughbreds, which is 13th all-time in North America and first among Canadian-born conditioners. He passed Merrill, who had previously been the leading Canadian trainer, in 2021. While the majority of his successes have been with allowance and claiming horses, Bennett has won the Grade I Philip H. Iselin Handicap and Grade II Michigan Mile and One-Eighth Handicap with Canadian bred Beau Genius in 1990 and has also trained such notable stakes winners as Secret Romeo, Banker’s Jet, Fast Flying Rumor and R Angel Katelyn.

But Bennett has had only two starters in the Tampa Bay Derby. Crimson Knight, whom he owned under his Winning Stables banner in partnership with Raymond Rech, finished second in 2011 as an 86-1 shot, defeated a neck by 43-1 shot Watch Me Go. In 2007, Bennett saddled Michael McQuade’s All I Can Get for a fifth-place finish in a Tampa Bay Derby won by subsequent Kentucky Derby champion Street Sense.

The Florida-bred Naughty Rascal is 4-for-6 with a second and a third in his career and owns three stakes victories, including the 7-furlong Pasco Stakes here on Jan. 11 via the disqualification of Owen Almighty for an incident involving another horse. But he has not faced a field with the overall depth of the Sam F. Davis, with Owen Almighty, unbeaten Grade II winner Poster and impressive maiden winner John Hancock prominent in the 10-horse field.

Still, Bennett believes Naughty Rascal possesses the combination of speed, stamina and courage to upset the proverbial applecart and take him to the Lambholm South Tampa Bay Derby in four weeks.

Both the Sam F. Davis Stakes and the Lambholm South Tampa Bay Derby are “Road to the Kentucky Derby” qualifying races, with the first five finishers in each awarded 20, 10, 6, 4 and 2 points.

Bennett will also saddle Life Is Precious, a four-year-old gelding he owns in partnership with Todd R. Bittiger, in Saturday’s $125,000, 6-furlong Pelican Stakes.

“This horse (Naughty Rascal) is what you wait for,” said Bennett, who trains the son of Rogueish-Baby Doll, by Smarty Jones, for the partnership of Ron Pugliese’s Mr Pug, LLC and Jim Georgeades’s J.P.G. 2, LLC. Pugliese and Georgeades purchased Naughty Rascal for $39,000 upon Bennett’s recommendation at the 2024 Ocala Breeders’ Sales March Sale of Two-Year-Olds in Training.

“He ran well (in the Pasco), but I didn’t drill on him too heavy because that wasn’t my main objective with him,” Bennett observed. “I didn’t want to overdo it because you might take a little of his edge off. It’s a fine line getting the fitness right, and Edwin (Gonzalez, who will ride Naughty Rascal again Saturday) said he might have gotten a little tired.

“He is getting better each race and he surely hasn’t peaked yet. I think he’ll get much better going around two turns – that way he can just relax. I think he’s coming up to this race just right,” Bennett added.

Bennett feels especially blessed to be on the doorstep of another Lambholm South Tampa Bay Derby opportunity. For a while last fall, he was unsure whether he would be able to participate in the current meet.

Late last summer, he was hospitalized for more than a week after undergoing surgery to remove four benign tumors from his colon and have a colostomy bag attached. His assistant, Juan Cacho Castro, ran the stable, with help from Bennett’s wife Mary and the conditioner’s numerous employees.

“The tumors were causing him so much pain – one of them was as big as my hand,” Mary said.

That wasn’t the end of his health issues. In September, he began chemotherapy treatments to treat cancer in his colon, liver and a lung. That regimen was halted last month when he underwent surgery to remove tumors from his bladder; they were benign but the blockage was causing him excruciating discomfort. He had to wear a catheter for five weeks, which made getting sleep extremely difficult – not that Bennett got his recommended amount previously.

Through his ordeals, his horses have still come first. “Even when he was lying in bed in all that pain, he’d say he had to check his phone messages,” Mary said. “He always has the horses in his mind. That’s what keeps him going.

“They are his life. A lot of people, they say they have a sixth sense about a horse. I think Gerry has a seventh sense. He can just look in a horse’s eye and get the vibrations.”

Pugliese and Georgeades, who have campaigned a few dozen horses with Bennett over the last nine or 10 years and become close to him and Mary, have listened to offers for Naughty Rascal as the wins accumulate. The colt has earned $220,630, so in a sense they are playing with house money.

Considering their friendship with Bennett and what this horse means to him, it would clearly take a whole lot of money to get them to think about selling.

“At the moment, we’re gambling,” Pugliese said, chuckling. “But if you’re running a 2 or 3-year-old colt at this point, you don’t take the money off the table. You’re rolling the dice. … if you win the Sam F. Davis, you might have a million-dollar horse. And if you run up the track in the Davis, what you have is probably a $50,000 horse.”

All three men are in the business to make money, but Bennett’s inspirational courage seems to bond them tighter each day, with each other and through their horse.

“I don’t know if there is a tougher person on the backside of the racetrack,” said Pugliese. “The day after his surgery, I called to check on him and I said ‘It sounds noisy. Where are you?’ He said he was at the (starting) gate with a horse. It’s amazing to me that he could be out here at 5 a.m. the next day, working horses.”

Pugliese and Georgeades accompanied Bennett on a recent trip to Solera Farm in Williston, outside of Ocala, to visit Naughty Rascal’s father Rogueish and look at horses. When they went to a restaurant after their trip, Bennett “ate like a prisoner going to his execution the next morning,” Georgeades put it.

“For a while we were worried about him because he was getting more frail, but he is coming back strong. You can see it in him,” Georgeades said. “But even when he gets tired and you start worrying about him, you just grit your teeth and bear with it, because you know how much this means to him.

“We’re not going nowhere. We’re going down with the ship,” Georgeades said, laughing. “This is one of the biggest challenges he has had. But if this horse turns out to be even better than what we think he is, the (Lambholm South Tampa Bay Derby) will be his next challenge.

“That is why we’re here with him – to get that far.”

That’s not to say they haven’t been tempted by a few six-figure offers they have received to sell the colt, whose stakes victories have come on dirt and turf, both sprinting and going around two turns. For now, though, money is secondary to the thrill of the experience they’re sharing.

The Bennetts are grateful to the doctors whose care has made it possible for him to stay at the track, and they are deeply appreciative of Castro and the barn crew’s efforts. And even Bennett, no sentimentalist, chokes up when he thinks of the concern and support he has received from members of the Oldsmar backstretch community.

But like his owners, Bennett isn’t going nowhere, either. To him, the terms “trainer” and “caretaker” have always been synonymous.

“Nobody I know takes care of horses better than he does,” said Georgeades.

Bennett loves dealing with such A.I. – Animal Intelligence.

“With me, it doesn’t matter whether it’s a really good horse or a claiming horse, a win is a win,” Bennett said. “When you’re a trainer, you’re just striving to win races.

“But this horse. … getting one like him, no matter your age or how long you’ve been in the business, it’s what keeps you getting up early every morning. You have new people calling, they put pressure on you, maybe you should sell. … well, you know how fragile the horse business is.”

He paused, fixing Naughty Rascal with a probing look.

“But you get very few chances to get to the Derby, and how many people spend millions of dollars to get there and be there that day?” he said. “So you either make up your mind you’re going for it, or not.”

He was talking about the other Derby now, the one on the first Saturday in May under the Twin Spires.

Hey, even 80-year-old guys can dream big.

-edited for space