Inside KY Native Gabe Prewitt’s 22-Year Journey to Lead Red Mile Sportsbook

For Gabe Prewitt, running the sportsbook at Red Mile in Lexington is a homecoming of sorts.

The 39-year-old University of Kentucky alumnus was introduced to the gambling world at the track during his time as a Wildcat. Growing up in Mount Sterling, about 30 minutes east of Lexington, Prewitt wasn’t exposed to gambling.

But that all changed when he enrolled at UK.

“When I got to Lexington, I actually wasn’t familiar with the Red Mile,” Prewitt told Gaming Today in an exclusive interview. “Never seen a harness race or anything. At some point, I had a buddy who said, ‘Let’s go to Red Mile and bet the horses.’”

That short, small-stakes gambling trip down the street was just the beginning.

Then, he began working entry-level jobs at the track.

Now, two decades later, he has accepted the role of vice president of racing and sports wagering operations for Red Mile. In that role, he will oversee the Lexington racetrack’s retail Caesars Sportsbook — the only confirmed sportsbook set to launch so far in Kentucky.

It’s only fitting that a native Kentuckian is the first major hire of the Kentucky sports betting industry.

College Job Jumpstarts Successful Career in Horse Racing

Prewitt started out as a ticket puncher and mutuel teller at Red Mile. However, he quickly picked up more responsibilities and became an integral part of the venue’s operation.

“I started here … in 2001,” Prewitt said. “(I) worked in the money room, this, that, and the other. Did some odd jobs and was the assistant mutuel manager at some point. But eventually, out of really a complete emergency status, they needed someone to announce the first couple races of the day.”

Prewitt tried his hand at announcing, but it didn’t go as planned. He described that first crack at it as “awful.”

“But I almost embarrassed myself into learning it and trying to get a little better,” Prewitt said.

He continued to hone his skills on the mic on a part-time basis during his first few years after college. Prewitt worked at Wells Fargo and Kroger after college, but his passion was horse racing. The announcing gig allowed him to keep his foot in the door.

As a result, he continued to improve and became the full-time track announcer for Red Mile in 2007. From there, more opportunities appeared.

“It eventually got to a point where I was able to make that my primary deal as far as doing a lot of TV work, analysis, handicapping and announcing,” Prewitt told Gaming Today.

Establishing Himself in South Florida

After several years of traveling for his new media career, he landed a job in 2013 at Pompano Park, a horse racetrack in Pompano Beach, Florida.

The Florida horse racing schedule gave Prewitt the flexibility to work in both Pompano and at the Red Mile.

“At that time, I was in my late 20s, and it allowed me to almost fill the time that Red Mile wasn’t racing,” Prewitt said. “I think we started in October and we raced through May. Red Mile would start in July and race through October. So, it was almost a perfect fill-in.”

During his 10-year tenure in South Florida, the track underwent several ownership changes. Consequently, his role gradually expanded.

“That ended up becoming more of a management role over time,” Prewitt said. “Partly because I always had an interest in it and I thought there (were) some things to try to grow the business, grow the handle. And then partly because they didn’t really have anybody else.”

When Prewitt was hired at Pompano Park, rumors were circulating that it was just about a year from going out of business. So, with little time to spare, the racetrack turned to somebody already on staff — Prewitt — to turn things around.

He took the opportunity and ran with it.

Little changes, like hanging post times of the races and the betting menu, immediately yielded results. Additionally, it yielded Prewitt a new title. On top of his announcing duties, he was named director of racing for Pompano Park.

Eldorado Realizes Prewitt Was Too Valuable to Fire

When Prewitt first arrived in South Florida, Pompano Park was owned by Isle of Capri. But after surviving a close call with bankruptcy, the track was bought by Eldorado Resorts in 2018.

At the time, it was just the second racetrack in Eldorado’s portfolio. While the company may not have had a ton of horse racing experience, it was established in the gambling industry.

And as Prewitt put it, Eldorado “sort of brought in their own people.” Just as quickly as he helped save the track, Prewitt’s job was in jeopardy.

“I wasn’t sure that I was going to continue a relationship with them,” Prewitt said. “They started the meet, which I had no problem missing because Red Mile was going at that time anyway. Ordinarily, I would’ve made plans to be there, but there was no guarantee that I would return.”

But the first Prewitt-less meet didn’t generate a ton of action.

The handle was down and Eldorado quickly brought him back into the fray.

Caesars-Eldorado Merger Gave Prewitt Another Promotion

In July 2020, Eldorado and Caesars Entertainment completed one of the largest mergers in US gaming history. Eldorado bought a 51% controlling stake in Caesars for $17.3 billion, but the new company kept the Caesars brand.

Therefore, Pompano Park changed hands for a second time. It was now a Caesars property. But unlike during the first ownership change, Prewitt’s job wasn’t in jeopardy.

Prewitt had an existing relationship with Caesars’ vice president of racing operations, Joe Morris. Morris used to run a handful of horse tracks in California and was familiar with Prewitt’s work in Florida.

When the merger was finalized, Prewitt was named Caesars’ director of racing.

Despite a new corporate title, Prewitt kept his announcing duties at Red Mile. Instead of traveling between the two cities on a seasonal basis, Prewitt would spend just a few days a week in Kentucky during Red Mile’s racing season.

Pompano Park Shutters Its Racing Operations

In February 2022, Caesars announced Pompano Park would be rebranded to Harrah’s Pompano Beach. As part of the rebrand, Caesars decided to close the horse track and expand its gaming floor.

As part of the track’s farewell ceremonies, Prewitt and announcing partner Pete Aiello jockeyed a harness race against one another to raise money for their chosen charities.

Pompano ran its final race on April 17. Then, the demolition process began. Prewitt’s corporate role with Caesars oversaw more than just Pompano, so his job wasn’t in jeopardy. But the 10 weeks of racing at Red Mile just wasn’t enough for him.

“It’s just not quite what I’m used to,” Prewitt said. “I need a little more action.”

Kentucky sports betting provided that action. And it came at the perfect time.

Prewitt’s Return to Red Mile Comes on a Full-Time Basis

Gov. Andy Beshear signed HB 551 at the end of March. It legalized online and retail sports betting in Kentucky.

The nine racetracks are all eligible for a retail sports betting license and to partner with up to three companies for online betting.

In May, Red Mile announced a partnership with Caesars Entertainment. As a result, the Red Mile’s retail sportsbook will be Caesars-branded. Furthermore, it ensures a Caesars Sportsbook platform for online betting.

Shortly after the partnership, Red Mile announced it hired Prewitt. The hiring brings Prewitt back home full-time and merges the two companies he’s worked at for the last decade.

“I still get to do a lot of what I’m accustomed to with live racing,” Prewitt said. “So it was almost the perfect setup for me. It allowed me to get involved in an industry that is new to the state. And it also allowed me, with the partnership with Caesars, to with some guys I know from my old role with Caesars. I’m sort of the liaison.”

About the Author
Steve Schult

Steve Schult

Sports Betting Writer
Steve Schult is a veteran of the gambling industry with more than a decade of experience covering the space. After earning his journalism degree from Marist College, the New York native began covering high-stakes poker tournaments and the U.S. gambling industry for various outlets. Following stints as a writer for Card Player Media, Bluff Magazine, and the World Series of Poker, Schult joined Catena Media and has managed coverage for a handful of states.

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