John Pentland considers himself a prudent person when it comes to training and his horses, priding himself on trying to make good business decisions for himself and his owners.

He readily admitted, in the conversation confirming the plan to supplement Redland Rocket Man to the 2026 Little Brown Jug, that the idea of spending $45,000 USD to race in the third leg of pacing's Triple Crown on Thursday, Sept. 24 is a "poor business decision."

That statement begs the obvious question of 'why?' Why would an owner spend that kind of money to race in the Little Brown Jug next Thursday, when there's a six-figure race four days later much closer to home? A race that likely won't be as difficult to win as the race you just won at that track in world record time?

Pentland truly understands that this specific situation — supplementing a horse to the Little Brown Jug  — is one he likely won't ever have to face again. And that's not to say that he'll never have a horse of this calibre again, although he recognizes that might be true. But it's a statement to the circumstances of this particular situation.

In 2025, Redland Rocket Man won three of his 12 starts, taking a mark of 1:52 at Woodbine Mohawk Park while banking $178,287 for Pentland and co-owners Murray Cox of Rockwood and Gary Volpe of St Thomas, Ont. A solid season, and a season where the competition included Beau Jangles, the eventual Horse of the Year in Canada and the U.S.  

But to say that Redland Rocket Man came out of nowhere to take his world record-tying 1:46.4 mark last Saturday in the Simcoe — defeating Beau Jangles, among others — would be disrespectful. Some 360 days ago, Redland Rocket Man finished fourth in the $1-million Metro Pace, just nosed out of third and two lengths back of winner Beau Jangles. Three months ago, this horse was one of 10 to race in the $1-million Pepsi North America Cup.

There, he finished eighth. Since, his trajectory has shot into superstar status.

The true eye-opening effort for Redland Rocket Man and his sophomore potential came in an Ontario Sires Stakes Gold leg on June 27 at Mohawk, when the son of Bulldog Hanover-Granny Hanover did all the work in a 1:48.2 mile won by Borderline Mobby. Back a head in second, Redland Rocket Man garnered kudos for his performance. The next OSS Gold leg solidified his position in the division, repelling Beau Jangles and Borderline Mobby in a 1:48.2 Canadian record mile at Grand River Raceway on Aug. 3.

He closed from the clouds to just miss in the Carl Milstein Memorial at Northfield Park on Aug. 15, then just got picked off by Beau Jangles in OSS action on Aug. 30. Last Saturday, driver Jody Jamieson made sure the tables could be turned and positioned the horse perfectly. The 1:46.4 mile time made history, matching the sophomore world record for three-year-old geldings held by Its My Show — coincidentally, the 2023 Little Brown Jug champ.

And here we are on Sept. 15 with a decision for Pentland and his connections to make. Be prudent, stay at home and race Redland Rocket Man in the Ontario Sires Stakes? Or target this prestigious and lucrative race under nearly ideal and planets-perfectly-aligned conditions?

This year marks just the fifth year that the Little Brown Jug has allowed supplemental entries. And it's a $45,000 USD decision that Pentland and his crew have willingly accepted as confirmed by Pentland to Trot Insider on Sunday night.

"I'll probably never have to make this specific decision again," said Pentland in a conversation early Monday afternoon. "And the reason I'm making it and it's so hard is because I did pay his two-year-old payment into the Jug. And when it came to it [at three], I'm going, 'well, there's a Sires Stake that conflicts.'

"I'm a prudent guy. I'm not cheap, but I'm prudent. And I wasn't going to throw $750 American away on something that I'm never going to do."

Never say never. Because when the list of supplemental entries is released on Saturday, Sept. 19, expect to see Redland Rocket Man's name listed.

"I'm trying to figure out, in 15-20 years from now, when the 80-year-old John Pentland is having a scotch on the back porch going, 'John, you were right. You did the right thing. You stayed home. You got a first or second in the next Gold. You didn't pay that $45,000 and look, we're living life okay and it made a bit of a difference.'

"Or does he say, 'you had your chance, you bastard. You had your chance and you let it slip. And what did you do with the money? You went and bought a yearling.'  And then probably don't remember the name of the yearling I bought."

Pentland and his connections are all in this time. And after a prudent approach to the horse's development to this point, Pentland and Co. want to experience this race and this event for themselves. The proverbial tires have been kicked on Redland Rocket Man, as others clearly feel this horse has what it takes to compete in Delaware, and beyond.

"Mark Weaver texted me and kind of said, 'Would you consider selling him?' And I basically said no," noted Pentland. "He said 'Fair enough. I'm not sure this three-year-old crop is as good as some previous years. I'm a little leery of how they'll do going forward, and I have some of the good ones too."

It's this perfect storm of conditions for Redland Rocket Man, harness racing's newest sophomore world record holder, and Pentland, who hinted at considering the Little Brown Jug after that world record win this past weekend.

"I think this colt could just go the two miles in a row," Pentland said in reference to the two-heat requirement after the Simcoe win.

Supplemental entries to the 2026 Little Brown Jug are due by Saturday, Sept. 19, 2026 at 10 a.m. Those currently eligible must submit their entry by Monday, Sept. 21, 2026 at 10 a.m., with the full list of entries to be released later that day.

(Standardbred Canada)