(Our Moneyman won the Crescent City Derby at The Fairgrounds / Photos by James Hodges — Hodges Photography)

From the Horseshoe Indianapolis Media Team:

Thomas, Calhoun hoping Our Moneyman can follow sire Mr. Money into Indiana Derby Winner’s Circle

By Jennie Rees, Eclipse Award Winning Turf Writer

 

SHELBYVILLE, Ind. (Monday, July 6, 2026) — They say money can’t buy happiness. But Mr. Money sure did, and now horse owner Chester Thomas is hoping for more of the same with Our Moneyman.

Seven years ago, Thomas’ 3-year-old colt Mr. Money sent the western Kentucky entrepreneur on one of the rides of his life, with a four-race victory streak that included the Grade 3 Indiana Derby at Horseshoe Indianapolis. Now Thomas and trainer Bret Calhoun have Mr. Money’s son Our Moneyman on a similar path as the state’s $300,000 signature horse race is staged for the 32nd time Saturday.

Both horses ran on the Kentucky Derby undercard, with Mr. Money winning the 2019 Pat Day Mile (G2) and Our Moneyman finishing third in a tough allowance race this past May 2. Mr. Money won Churchill’s Matt Winn (G3) in his next start, then went on to take the Indiana Derby and West Virginia Derby (G3). Bred by Thomas in Louisiana, Our Moneyman rallied to be a good second in the June 7 Matt Winn behind Further Ado, who in the spring had won Keeneland’s Grade 1 Toyota Blue Grass by 11 lengths.

“Mr. Money had a great campaign in 2019, and it’s so exciting to be racing his offspring,” said Thomas, whose Allied Racing Stable had career-best seasons in 2019 and 2020, his horses running out $2.5 million and $2.3 million, respectively. “My wife, Jennifer, bought his dam, Lipstick Junky, at the Keeneland yearling sale, and she’s been named Broodmare of the Year down in Louisiana (in 2022 and 2025).

“We take it one race at a time. But yeah, if we could just win one of these races, we’ll see where we go from there. But the horse came out of his race doing really well. He’s eating his feed. He’s training well. He’s happy. He owns his part of the shedrow down there, so you gotta be careful when you go by. But he’s on his game right now.”

Indeed, the Matt Winn second to the highly regarded Further Ado was almost as good as a win to Our Moneyman’s team.

“Unfortunately, we were boxed in pretty well all the way around the second turn in the Matt Winn,” Thomas said. “We were loaded with horse at the three-eighths pole. We had to spot Further Ado a couple of lengths, and we belatedly kept up with him. But you’re not going to beat a horse like Further Ado that gets the lead at the top of the stretch and gets a jump on you. He’s a super nice horse, so we came out there feeling pretty proud with a second-place finish.”

Axel Concepcion, winner of the 2023 Eclipse Award as North America’s outstanding apprentice jockey, will be back aboard after riding Our Moneyman in every start.

After winning a Keeneland maiden race in his second race, Our Moneyman went with Calhoun’s stable to Louisiana for the winter. He ran in four stakes for Louisiana-breds, with two wins and a second, including victory in the $100,000 Crescent City Derby in his first start around two turns. The Derby Day allowance race was Our Moneyman’s first start back in Kentucky, where he again ran into tougher open company.

“We were pretty optimistic about him going into his 2-year-old year, and he performed well down there at the Fair Grounds this winter,” Calhoun, speaking recently at Churchill Downs, said of last year’s champion Louisiana-bred juvenile. “We had a couple of hiccups here and there, some bad luck, but he’s really kind of figured things out now. I thought he ran well in the allowance race here. I thought he was probably the best horse that day, just had a little wide trip. So it gave us a little confidence to go back in the Matt Winn.

“Obviously, we knew it was going to be a tall order there if Further Ado ran his race, and he did. But I thought we ran a very, very good race against him that day. So that had us thinking about the Indiana Derby. The horse is really continuing to move forward. We think he’s doing very well, and he’s got a real chance in the Indiana Derby.”

Calhoun, who also won the 2021 Indiana Derby with Mr. Wireless, said Our Moneyman shares Mr. Money’s temperament.

“His mental part of it is a lot like his daddy: very quiet, very smart horses, nothing seems to bother them,” he said. “And this horse probably wasn’t as far along early in his career, even though he was pretty accomplished, as Mr. Money. He seems to be getting kind of to the point where Mr. Money was now.”

Thomas said he’s had inquiries about purchasing Our Moneyman. But, after all, he named the horse Our Moneyman, not Your Moneyman.

“We’ve had a lot of interest in Our Moneyman since his race Derby Day, and even more interest since the Matt Winn,” Thomas said. “But you spend a lot of time and money breeding horses. The good ones don’t come around very often, and so it’s really why we do what we do. So why just get rid of it? I mean, it’s been a dry spell for us. We’ve had some nice horses, but not any super nice horses, and so we’re excited. We’re going to go to Indiana with our fingers crossed and hopefully end up having a fun night.

“It’s not gonna be easy. Hopefully, the horse shows up, and maybe we get a little bit different set up this time, and get a chance to get a jump on them rather than have to try to play catch up.”

A neck defeat in the Grade 1 Pennsylvania Derby to Math Wizard (who Mr. Money beat in the Indiana and West Virginia Derbys) probably kept Mr. Money from standing in stud in Kentucky. Thomas and Spendthrift Farm, which had bought into Mr. Money after the Pennsylvania Derby, thought his best chance to make it as a sire was in a regional market. Two years in Florida proved unproductive, but Mr. Money has gained traction since moving to Clear Creek Stud in Folsom, La.

Our Moneyman is Mr. Money’s leading money-earner at $332,667.

“He’s been a very good regional sire with not much help,” Calhoun said. “He spent the first couple of years in Florida, and that didn’t go well down there. He didn’t get a lot of support and didn’t really have many foals. He’s done very, very well with the opportunities he’s had.”

Siring a winner of the Indiana Derby “would be a big feather in his cap, a huge promotion for him,” Calhoun said. “This is his first year to have a full crop of 2-year-old Louisiana-breds. So hopefully he’s going to have a lot more in the pipeline.”

The 24th season of live Thoroughbred and Quarter Horse extends through Friday, November 13. For more information on racing at Horseshoe Indianapolis, visit www.caesars.com/horseshoe-indianapolis/racing or find details on social media @HSIndyRacing.

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