Boston Sports Heroes Who Could be Sports Betting Endorsers for Massachusetts Sportsbook

Bostonians are a provincial lot, from their fanatical loyalty to Dunkin’ to sticking with Ben Affleck through the tough times. So it stands to reason that with legal sports betting coming to Massachusetts, a savvy sports betting operator would be wise to employ one of Boston’s venerable sports heroes to direct them into their sportsbook or onto their app.

There are a lot of choices, especially considering the rabid — pro and con — nature of fandom in the commonwealth.

Retired players are a sound move, although Major League Baseball and the National Hockey League allow active players to endorse sportsbooks under certain conditions. But there appears to be somewhat of a rethink in the sports betting industry about whether athlete endorsers are worth the cost in terms of the business they attract. And a recent request from pro player unions to Massachusetts regulators for greater player protections from disgruntled bettors may signal that athletes wish to keep a distance.

But if there was a place where the cranberry juice was worth the squeeze, it’s Massachusetts.

Wicked Choices


Tom Brady

Is it commonwealth law that all lists have to start with Tom Brady?

In this case, it’s alphabetical but no less appropriate. A six-time Super Bowl champion as quarterback of the New England Patriots, Brady, 45, remains a popular and influential figure despite plying his trade elsewhere and even winning another Super Bowl with Tampa Bay. The good times have faded in his absence, so a little more GOAT on billboards and on local TV and radio might make for warm memories on cold October nights.

He announced his retirement Wednesday — and he says he means it this time — and Brady is slated to join Fox’s NFL broadcast in some capacity, which would seem to cue him up as a sports betting pitchman for Fox Bet in keeping with the way the network has utilized Terry Bradshaw and Howie Long. CEO Lachlan Murdoch said last year that Brady would, along with booth work, serve as an “ambassador” for Fox, including “client and promotional initiatives.”


Kevin Garnett

The Hall of Famer played six of his 20 NBA seasons with the Celtics, deploying defensive tenacity and otherworldly trash-talking abilities to help win the franchise’s 17th title in 2008.

Garnett’s post-NBA career has threaded through the sports betting sector multiple times. In 2019, he was a side character in the Adam Sandler sports betting vehicle, Uncut Gems, and damn it, he can act a little bit. In 2021 Garnett co-founded the bet-centric Gaming Society media platform and a year later joined BetMGM as a sports betting ambassador, once again deploying those acting skills.


Rob Gronkowski

“Gronk’ and FanDuel will make their Super Bowl ad debuts together on Feb. 12. In a highly-publicized campaign the former Patriots tight end is apparently taking quite seriously, Gronkowski can earn FanDuel bettors a chance at a share of $10 million by successfully drilling a field goal.

Gronkowski clearly has the charm and the gravitas to pull this off and at 33 is still relevant. It would be interesting to see Gronkowski leading the charge for FanDuel, whose rival, Boston-based DraftKings, had an early investor — and still, roughly a 5% owner — in Patriots owner Robert Kraft.


Brad Marchand

Unquestionably talented and universally reviled outside of Boston fandom, the Bruins winger, 34, could shill for a brand under NHL guidelines and Massachusetts sports betting statutes that say only “No advertising, marketing, branding, and other promotional materials published, aired, displayed, disseminated, or distributed by or on behalf of any Sports Wagering Operator shall contain images, symbols, celebrity or entertainer endorsements, or language designed to appeal primarily to individuals younger than twenty-one years of age.” He just feels like a Barstool guy waiting to happen.


David Ortiz

The beloved Red Sox slugger and Hall of Famer helped the city move to a new phase of healing in 2013 when he proclaimed in a pre-game ceremony in the first game following the Boston Marathon bombings, “This is our f—— city.”

As the Red Sox recede into what could be a tough era in the AL East, Ortiz would be a reminder of a period when Boston won three World Series, including, in 2004, the first in 86 years. With Xander Bogaerts gone, there doesn’t seem to be a natural active-player fit in terms of aura and production.

Big Papi is already in the business as a pitchman for Fox Bet, so it’ll be interesting to see how much sway he still possesses in the ancestral homeland of DraftKings. He and Brady could make DraftKings actually work for its Boston bucks.

Unless …. he somehow double-dips. In a very interesting move proving how shrewd DraftKings can be and how lawyers can fix anything, Ortiz landed a spot in DraftKings’ Super Bowl LVII ad.

It stands to reason that if DraftKings can secure his services for the future, he could be a massive help in Massachusetts.


David Pastrnak

“Pasta,” a star right-winger for the Bruins, has already proved his pitchman skills with a national … wait for it … Dunkin’ ad and seems fit to lend his humor and charisma to whatever local operator could use him. DraftKings is the official daily fantasy partner of the team.

About the Author
Brant James

Brant James

Senior Writer
Brant James is a senior writer who covers the sports betting industry and legislation at Gaming Today. An alum of the Tampa Bay Times, ESPN.com, espnW, SI.com, and USA Today, he's covered motorsports and the NHL as beats. He also once made a tail-hook landing on an aircraft carrier with Dale Earnhardt Jr. and rode to the top of Mt. Washington with Travis Pastrana. John Tortorella has yelled at him numerous times.

Get connected with us on Social Media