Ontario trainer John Pentland said winning the Little Brown Jug was never on his bucket list. That’s not because he didn’t very much want to win it, just that it seemed so improbable he didn’t dare to dream that big.

On Saturday, Sept. 26, two days after his Ontario-sired pupil Redland Rocket Man and driver Jody Jamieson did indeed win the 81st edition of the Grade 1 Little Brown Jug at the Delaware County Fairgrounds in Ohio, Pentland was still grinning as he stood on the tarmac at Woodbine Mohawk Park – and that was before another of his Ontario-sired pupils, two-year-old pacing filly Jersey Bulldog, won the Grade 1 Shes A Great Lady Stakes out of the nine-hole later that night.

Over the last fortnight, in particular, fate has been grinning at Pentland.

Nearing 30 years into training his own stable, Pentland is well aware that, for some reason, the planets have aligned for him. He’s also cognizant that it wasn’t that long ago that he was struggling to keep going in the business.

In 2016 and ‘17, Pentland had back-to-back years when his stable earned less than $100,000 each year. In the fall of 2017, the trainer from Dorchester, Ont. scraped together $12,000 to buy Betterthancheddar pacing filly Powerful Chris from the sale now called the London Selected Yearling Sale.

“I only had $11,000 and I went to the sale and I bought her,” said Pentland. “She trained down phenomenally and I didn't even have the money to stake her.”

In her career pari-mutuel debut on July 10, 2018, in an Ontario Sires Stakes (OSS) Grassroots event at Woodbine Mohawk Park, the pacing filly won by nearly nine lengths and looked “phenomenal” doing it.

“I knew right in that instant my life changed,” said Pentland. “Tammy McNiven said to me, ‘I can't believe how happy you are, John!’ And I said, ‘My life just changed.’ I got her priced. Somebody tried to buy her for $270,000 and so Bob [McClure] got his grandfather to buy a quarter because I didn't really want to sell her, but I needed the money. I simply called Jack [Darling] for direction. I said, ‘Could you put me onto somebody that would be interested?’ I never thought for a second Jack might want in. Jack goes, ‘I'll take a quarter.’ Ever since then, he and I have owned some horses together. He’s been really instrumental [in my comeback].

“Jack Darling played a big role in that. He gave me horses to train to help me get back on my feet.”

Both Redland Rocket Man and Jersey Bulldog are offspring of Ontario-sired and based stallion Bulldog Hanover. Outside of Darling, who picked out, purchased and trained Bulldog Hanover, Pentland said he is probably the horse’s biggest fan.

“I watched 'Bulldog' and I never missed a single race,” said Pentland. “I was absolutely hooked on him… At the end of his three-year-old season, he was just head and shoulders better than everybody.”

That explains how Pentland came to purchase Redland Rocket Man, bred by Redland Farms in Bible Hill, N.S., for $41,667 out of the Preferred Equine consignment at the 2024 Standardbred Horse Sales Company’s yearling sale in Harrisburg, Pennsylvania. It was the year Bulldog Hanover’s first crop was selling – a select group of just 54 foals with only 35 sold at auction.

A year later, Pentland said he and Darling partnered to try to buy a Bulldog Hanover offspring in Harrisburg. They landed on Jersey Bulldog – a filly out of Somebeachsomewhere mare Gallie Beach bred in New Jersey by Mark Mullen and Stephen Dey – and took her home with a bid of $56,338.

“Both of us loved this filly and we'd have [paid] a lot more,” said Pentland. “We got her for $40,000 [USD] and I'm sure we'd have gone $60,000 or $70,000 [USD].

“She’s push button. She’s like chocolate ice cream. It can’t be better. It can only be that good.”

The trainer said while he couldn’t conceive of ever winning the Jug, winning the Shes A Great Lady has been on his bucket list for 20 years.

In 2006, he finished second in the race, three-quarters of a length back, with Luck Of Michelle.

“It was the first Grand Circuit race [I almost won],” said Pentland. “Luck Of Michelle was so close to winning. I had another filly that was third in it another year.”

The journey from there to here has been a long one for Pentland, but Sept. 12 may have been another indication that his life had changed for the better. That night, both Redland Rocket Man and Jersey Bulldog won Grand Circuit races at Woodbine Mohawk Park – the former with a 1:46.4 sophomore Canadian record and world record for three-year-old pacing geldings that convinced the trainer to pay the $45,000 USD supplemental fee to make the gelding eligible to the Jug.

Here again, the "Racing Gods" intervened in Pentland’s favour. This is only the fourth of the Jug’s 81 years that open supplements have even been allowed.

“I was flirting with the idea [of supplementing Redland Rocket Man], but had I not won that race [in 1:46.4], I probably wouldn't have gone,” said Pentland. “When he beat them, and beat the Canadian record, it was like, ‘If you were considering it, how can you not go now?’”

Pentland credits Murray Cox and Gary Volpe, his ownership partners on the horse, for allowing him the space to make the call on paying the supplement.

“I had no pressure from them one way or the other,” said Pentland. “If I had decided not to do it, I might have disappointed them, but they weren't going to lean on me. They sort of allowed me to make the decision, or maybe they coaxed me and I was just too naive to know it.

“They're all in as owners and they're both terrific owners, and they've had horses for a long time with a bunch of guys and I'm lucky enough to have snagged them right now… And my crew, they're close friends, the four main people that work for me, and my wife has been with me on all of it. We all did it together. I made the final decision, but we all did it together.”

Minutes after winning the Jug, Pentland said he had 130 text messages congratulating him. Jamieson had 240.

“[Ontario horsewoman] Jody McGilveary sent me a message,” said Pentland. “She said, ‘John, everybody was under the TV [at Woodbine Mohawk Park] yelling and cheering, and when it was over, they applauded.’ I've been in that scenario in the paddock with one of my competitors winning a big race and we all love it. Go Canada! We cheer for each other even though we’re competitors on the track.”

Two days after his biggest career triumph, Pentland said he’ll have the memory for a lifetime.

“I've had great nights,” he said. “I've had a good career, but it’s the Jug. We won the Jug… They can't take it away. There's no other race you want to win more. You might want to win a race just as much, but there's no race you want to win more.

“One day, I'll sit on my back porch drinking a scotch, thinking, ‘You took the chance, and it paid off.’”

Putting that $45,000 USD supplement fee in perspective, Pentland said trainers, “take chances every fall. I'm about to go take a whole bunch of chances in the next couple of months, and you know what? Honestly, this is better. [The Jug] was a better opportunity than just going to buy a random yearling.”

That Pentland is having a career year given all this is not surprising. But his numbers are truly impressive. With three months left in 2026, he has already had his best year in earnings with more than $1.75 million made and has his second most wins (35, two short of his personal record of 37 set in 2024). This is just the second time Pentland's had earnings of more than $1 million in a single season. The first time he hit seven figures was 20 years ago in 2006, the year he campaigned Luck Of Michelle.

The moral is this: Sometimes, the fates can be cruel, like they were 10 years ago; sometimes, they can smile upon you with the radiance of a thousand suns.

On the walk back to the paddock after winning the Shes A Great Lady, the trainer stated the obvious as if he was trying to put that gratitude into the universe.

“It’s good to be John Pentland right now,” he said, still grinning.

Odds are it will be a long time until that smile leaves his face.

(Ontario Racing)