When Benny Havens won the third start of his career six years ago, owner-trainer T. J. Aguirre probably had in mind winning several more races, maybe a minor stake or two.

What he got instead was a 39-race losing streak – a streak that Benny Havens snapped today with a gratifying win in a $48,000 Maryland-bred/-sired allowance.

“I said one day, he’s gonna win this race, and it’s going to be the best day of my life,” Aguirre, holding squirming one-year-old son Cooper, said afterwards. “I’m just gonna keep rolling with that, and it happened.”

Under jockey Weston Hamilton, Benny Havens was in sixth early, saving ground while several lengths off a fast, contested early pace. Sinetic and Great Kisser dueled through rapid early fractions: 21.86 seconds for the opening quarter, 45.50 for the half.

Hamilton swung his mount outside for a late charge, and Benny Havens prevailed by a head over 2-5 favorite Call Me Andy, with Claudee Boy another neck back in third.

Benny Havens paid $28.80 to win and topped an exacta that returned $56.70 for a buck. He now has two wins from 43 career starts to go with earnings of $155,851.

Jockey Sheldon Russell had ridden Benny Havens four times last year and in his first start of this season, when finishing fifth April 25. With Russell’s wife Brittany Russell sending out Daring Venture in this spot, Sheldon Russell went with that runner.

“Sheldon says he needs the right trip, the right race, and I think we got it today and it worked out well,” Aguirre said. “Weston rode a great race and put him in position, and here we are in the winner’s circle again.”

About that: Wes Hamilton has ridden Benny Havens intermittently over the years but mostly when the now-eight-year-old was two and three. Among his prior starts with the Outflanker gelding was his maiden breaker on Sept. 6, 2019.

And then came the losses.

The thing about the losses, though, is this: all of them, all 39, came in stakes, allowance, or starter allowance company. Not once since a dip into the claiming ranks to break his maiden has he run for a tag.

“This was the first horse I ever purchased, and I built a bond with him over the years,” Aguirre explained. “He won an allowance race as a three-year-old and got disqualified, and it kind of gave me hopes that he could be a decent horse.”

The other thing about the losses: even as they piled up, Benny Havens continued to run good races. In his final start of 2024, he was beaten less than a length while earning a career-best Beyer speed figure of 79.

“Sheldon told me when he rode him last year, bring him back next year as an eight-year-old if he wants to do it,” Aguirre said. “And the horse told me from the start, he was like, ‘I’m not done.’ I brought him back into training, and every step of the way, he said, ‘I’m back.’”

With an eight-year-old, you’ve got to take things one step, one day at a time, and Aguirre plans to do that. Most likely he’ll go hunting a first-level allowance for Benny’s next start. With, perhaps, a lesson learned.

“He loves his job, he loves doing this, and it shows that you don’t give up on them,” Aguirre said. “I just never gave up on him because every morning, he never gave up on me.”

NOTES For the second consecutive day, Pimlico stewards declared a race “no contest” after the gate malfunctioned. Yesterday, the horses in the first race actually ran the race, with those allowed out first prevailing before the race was voided. Today’s second had the same problem, though this time the runners were pulled up by the time they hit the first turn… Pimlico hosted the National Thoroughbred League today with Baltimore Ravens quarterback Lamar Jackson on hand. No idea which team won, though Jackson’s hat was a highlight…