BOSTON — A collection of bleary-eyed parents pushing baby strollers, college-aged kids sleeping on benches, and a group of spry senior ladies had gathered in the waiting area of North Station under TD Garden in July.
By their apparel, many had taken in the Red Sox game the previous evening and were bound via incoming Amtrak train for somewhere north, anywhere from New Hampshire to Maine, where the excited ladies would later have brunch at a bed and breakfast.
Most of them gripped Dunkin’ coffee cups to rage against the hour. Over in the corner, by the grubby exit of the station, a line of 10 waited to order.
Near the entrance to the station, a Starbucks stood open and mostly vacant. All these early morning commuters had foregone the first available caffeine to wait in the Dunkin’ line.
Locals will grumble that the ever-present chain isn’t what it used to be when it opened as a donut shop in Quincy in 1950. But it remains the local habit. Especially iced. Even in winter. These Bostonians like what they’re used to.
This probably bodes well when the home teams of sports betting can start taking mobile and online wagers in Massachusetts on Friday, March 10.
Boston native Kevin Mercuri, CEO of Propheta Communications, told Gaming Today:
Having lived in three major cities, I can say Bostonians take provincialism to a higher level than most. They tend to be very brand-loyal toward their hometown companies, their hometown celebrities, and more.
“If DraftKings were to brand themselves as the hometown sportsbook – and feature the fact that hometown hero Robert Kraft is a partner in the enterprise – they could easily capture a larger percentage of the Boston Area market.”
DraftKings was formed in Boston, has an office on Boylston Street, and its logo on the Green Monster at Fenway Park stands out like a Dropkick Murphys tattoo.
But there’s another local entry, fronted by local-boy-made-big-time-big Dave Portnoy. The bro-centric ethos that underpins his Barstool Sports feels very much in keeping with the image of the Boston fan, the one who would absolutely donate all of their organs if Brad Marchand needed them.

Certainly, major national brands will compete. FanDuel Sportsbook is even brandishing former Patriots tight end Rob Gronkowski as a brand ambassador.
This contest has the potential for a delicious Good Willing Hunting-level of class conflict, considering who each is hoping to attract, and how.
One week after @DraftKings went live with mobile sports betting in our home state and it’s still a bit surreal. The team did an amazing job with the @DKSportsbook Massachusetts launch and our 1300+ MA employees get a chance to see their hard work play out in our own backyard. pic.twitter.com/SItKpS4eYl
— Jason Robins (@JasonDRobins) March 17, 2023
Related: Massachusetts Gaming Regulators Look Favorably on DraftKings Local Ties
Sportsbooks Brandish Local Heroes, Survey Tabs Boston Bias
A study released this week by PlayMA found that 62% of respondents said they were likely to patronize DraftKings because of its Massachusetts base.
That’s bad news for its traditional rival. FanDuel claimed in its fourth-quarter earnings call a nation-high 50% market share and leads in 15 of the 18 states where its offering bets. That lead was mainly driven, according to FanDuel data, by customer acquisition through referrals.
FanDuel, like DraftKings, has exploited its existing daily fantasy sports user base as states have legalized sports betting since the repeal of the Professional and Amateur Sports Protection Act in 2018.
While celebrity sports ambassadors had been a rage for several sportsbooks over the past two years, the industry has generally coalesced around the sentiment that they’re not worth the cost. While the Manning family is still a prevalent Caesars resource in television ads, jock endorsement splashes have recently centered more around major events, such as David Ortiz shilling for DraftKings and Rob Gronkowski for FanDuel in Super Bowl commercials.
“Boston’s always been a town that’s been based off of personality,” B2 Global managing partner Brendan Bussmann told Gaming Today. “So this may be one of the markets that’s just going to be different across the board anyway because of the battle that has gone into getting licenses to this point.
“Every licensing process has not been easy. It’s been long conversations with each and every operator. So I think personalities can shine in this, to some extent. It’s going to about product and what people are familiar with.”
“Massachusetts presents an interesting challenge for FanDuel, as it’s one where they don’t start with a level playing field due to DraftKings hometown advantage,” Chip Tuttle, a partner at the Boston-based CTP advertising and public relations agency, told Gaming Today. “DraftKings has a really strong DFS position, established marketing relationships with the major pro franchises and popular local spokespeople, including David Ortiz. Papi is an icon here but Gronk can go toe-to-toe with him.”
CTP has worked with numerous players in the Massachusetts sports betting churn. It handled public relations for DraftKings during the regulatory process and worked with FanDuel and its TVG.com horse racing platform. It’s also handled accounts for the Red Sox, Dunkin’ and Ortiz with Boston-based Eastern Bank.
“The acquisition battle is already raging here, and it will get more competitive heading into March Madness as the major players fight for market share,” Tuttle said. “This is a market with a really strong affinity for the professional sports teams and with two sports radio stations that dominate local ratings.
“It feels like two out of every three radio spots are for sportsbooks now, and media outlets that were once exclusive have dropped that to take advantage of the spending spree.”
Is Barstool’s Portnoy Still a Boston Common Man?
Tuttle wonders if Barstool’s deep Boston roots will resonate, no matter the level of fandom Portnoy still feels for his hometown or that his company “for better or for worse,” he said, took on the city’s personality. Even though Portnoy’s gambling magazine first circulated in the streets of Boston in 2003, Barstool and the Swampscott boy now seemingly belong to everyone of a certain demographic, whatever hockey jersey they wear.
— This Day In Barstool Sports (@ThisDayInBSS) March 5, 2023
The Barstool brand, though still ubiquitous, especially with its target 20-something male demographic, was purchased by the PENN Entertainment conglomerate with the $388 million acquisition recently completed. It could use some home cooking, as it accounts for only about 5% of national sports betting handle.
“It’s harder to gauge how Barstool and PENN will do,” Tuttle said. “While Barstool was born here and has some residual strength in the market, it’s been a national platform for a while. They haven’t been as visible as some of the other major brands but that’s not a surprise as they rely on their own media platform.”
DraftKings is certainly a national player, too, having transformed into a more polished, mainstream-accepted brand after its rougher-edged early days as a DFS platform. It’s been offering its wares in fantasy and sports betting much longer in Boston and elsewhere, though, than Barstool, which launched its sportsbook app in 2020.
Bussmann said Barstool improved its local position by partnering to open a sportsbook at Plainridge Park Casino, one of three allowed to begin taking retail bets on Jan. 31.
Massachusetts Casino Sportsbooks May Have Home Edge
But Bussmann noted that there’s another home team in the mix. It’s a Wynn property sitting on the bank of the Mystic River in Everett.
“I think that the third one I’d throw in there is … a phenomenal property in Encore Boston Harbor,” he said. “That has also become the local favorite. And to the same extent, obviously, on the west side [of the state], MGM [Springfield] takes care of the whole mix.
“But when it comes to online, I think there’s going to be a lot of turf battle. And I say that from the standpoint of everybody in Boston, as much as you talk about people waiting in line for Dunkin’, they also want to make sure that local guy hopefully ends up on top just because it is such a competitive market over those types of things.”
Bussmann added that an industry-wide customer acquisition austerity trend may also leave the market more to figure itself out. This wasn’t the case before the online sports betting launch in New York last year or in the media blitz preceding voting on two sports betting measures in California.
“It’s always anybody’s game coming out of the chute,” Bussmann said. “Product database and marketing all matter in being able to capture that market share. I think everybody’s going to be competitive. The difference that you have here that you don’t necessarily have in other markets, is you have a Wynn brand and a Barstool brand basically on the ground. So as opposed to just being the Caesars, BetMGM, DraftKings, FanDuels of the world that typically take up the top four, I think it’s much more of a six-person race.”
And maybe a fighting chance to not be the Starbucks of Boston sportsbooks.
UPDATE: DraftKings led all operators in March with 47% market share. Barstool managed 5%.