Massachusetts Gaming Commissioner Jordan Maynard has a soft spot for the “commonwealth”. Sure, he loves the Commonwealth of Massachusetts, but the Commonwealth of Kentucky is his home state. So Maynard was happy to help when Kentucky Horse Racing Commission Chair Jonathan Rabinowitz asked him for advice on Kentucky’s upcoming sports betting rollout.
His number one tip? Stick to a launch timeline.
The Kentucky General Assembly made that easy by mandating that the KHRC launch Kentucky mobile and retail sports betting no longer than six months after the state’s 2023 sports betting law takes effect in late June. That puts Kentucky on track for a late December launch, although officials have hinted at a quicker pace.
“That was something that (the MGC) had to hammer out, just that part – what does the deadline look like – because the legislature left it up to us,” Maynard told Gaming Today in an exclusive interview on Wednesday. Massachusetts implemented a staggered launch beginning with retail in January, then mobile in March.
Since launch on Jan. 31, Massachusetts sports betting has generated more than $1 billion in handle – most of that coming from mobile, which went live on March 10.
“I have been in contact with Chair Rabinowitz, and the first thing I said to him was, ‘We met 80 times between Aug. 1, which was the day (our bill) passed and the day we launched Category 1,’ or casino sportsbooks,” said Maynard. “One thing we had at our disposal is we were very nimble,” thanks to online meeting technology established during the pandemic.
“But I do think it’s going to take a lot of work.”
Tip #2: Seek Advice from Other States
Maynard is from Pikeville, in eastern Kentucky. He is the first member of his family to graduate from college, he said. He is also a Kentucky-trained attorney and a member of the Kentucky bar.
Since arriving in Massachusetts initially for his wife to attend law school, Maynard has worked in several government positions including the role of Chief Secretary and Director of Boards and Commissions for then-Gov. Charlie Baker (now NCAA President). He began serving as an MGC Commissioner last summer – just in time to help the five-member commission begin months of sports betting hearings.
Luckily, Maynard said, the MGC didn’t have to come up with a sports betting program from scratch. It relied on advice from other jurisdictions to get started. That was his second tip to Rabinowitz.
“He asked me a general question which was, ‘What would you say to yourself going back in time?,’ and my advice was, listen to the experts,” said Maynard. “Cast a wide net. You’re going to hear from a lot of different stakeholders and try to be as open-minded as you can.
“Outside of a couple jurisdictions, this is all new as of 2018 and rolling forward. So if we don’t rely on each other here, it’s almost impossible.”
Kentucky is now surrounded by legal sports betting states. Learning what works, and what doesn’t, from states already in the game will maximize efforts down the road, Maynard explains.
“Any minute that goes by when you’re in a state surrounded by legal jurisdictions as well as having illegal bookies being in the state, any day that goes by once legislation passes that and the gov signs it is a missed opportunity,” he said. “It’s a missed opportunity to bring tax revenue into the commonwealth, it’s a missed opportunity to help someone who may have addiction behaviors get into assistance.”
Tip #3: Draw on Your Own Experience
Still, Maynard knows that every state is different. That’s true with the commonwealths of Massachusetts and Kentucky as well. Massachusetts has legal casino gambling; Kentucky doesn’t. Kentucky has several active horse racetracks; Massachusetts has one. Massachusetts has pro sports franchises and college teams – Kentucky is a collegiate sports state only.
Kentucky sports betting will be tethered to the state’s nine racetracks, each allowed one retail sportsbook and up to three mobile sports betting apps. Massachusetts has three casinos (including one with live racing), each allowed one retail sportsbook and up to two mobile apps, with mobile apps licensed separately.

Massachusetts also has two former racetracks (Raynham and Suffolk), each allowed a retail sportsbook and one mobile app, although neither Raynham nor Suffolk have launched their sports betting operations.
Raynham – a former greyhound track and now a simulcast facility – is planning to open a Caesars Sportsbook this year. Suffolk Downs currently offers horse race simulcasting but has not applied for a sports betting license. The former track and surrounding area are under development as a residential, retail, and open space.
Maynard said it will be up to the KHRC to decide how to regulate sports betting through a track-based system. But he doesn’t think Kentucky will start from scratch. Like Massachusetts, he expects Kentucky will use existing regulations and licensing procedures as a guide.
“Our application was drawn from the original application for brick-and-mortar casinos. They’re going to find the same thing,” Maynard explained. “They’re going to find places where they can develop processes and systems, and they can retool those and use them for the sports betting side.”
Tip #4: Expand Your Traditions
Plainridge Park Casino (PPC) is the only active horse track in Massachusetts. It also houses a brick-and-mortar casino, and it is now a sports betting destination too, with a retail sportsbook and two mobile sports betting apps (Barstool and Fanatics).
Since launching its retail Barstool sportsbook, Maynard said, PPC has told him that it has seen more foot traffic. That could bode well for Kentucky, where horse race betting participation has dwindled over the past decade.
“They have definitely seen more foot traffic just looking at their numbers,” Maynard said about PPC. “They’re doing well as far as the money goes.”
He won’t make any predictions about Kentucky, but Maynard said PPC’s numbers show there’s a benefit to adding “a new amenity to a very traditional watching-and-wagering experience” – with “traditional” being the operative word.
Horse racing is a Kentucky tradition in every sense of the word. Adding new forms of gambling has been controversial in the past, starting with the addition of historical horse racing (HHR) machines (electronic gaming machines) to the state’s gambling landscape. Those machines drew legal challenges eventually put to rest by changes to state law.
A Place for Sports Betting in Kentucky
Legal sports betting has also drawn opposition in Kentucky, but not from the horse tracks. They want the foot traffic and revenue that legal sports betting will bring. Maynard says there is room for both types of wagering, in his opinion.
“I think being responsible is key. Whether you are talking about the type of wagering at a horse race or you’re talking about sports betting,” he told Gaming Today. “Horse racing in Kentucky is a great tradition. But so are sports.”
“The interesting thing about sports wagering, and wagering in general, is with the catalog there’s something for almost everyone to have an interest in. I think that it fits with the tradition of Kentucky. And as long as it’s being done responsibly for entertainment value only, it’s okay to expand your tradition.”
Maynard’s last bit of advice for KHRC regulators as they continue to build out a Kentucky program?
“Tune out the talking heads. And to me, the biggest pitfall to avoid is not gathering enough information. Be open-minded. This is new. Rely on other jurisdictions. And always keep in mind what is important for your state.”