Breakdown: Which Boston-Area Native Is The Sports Betting GOAT: Portnoy or Simmons?

Written By Frank Weber on May 24, 2022Last Updated on January 27, 2023
Which Boston native is the sports betting G.O.A.T.: Portnoy or Simmons?

The Boston area has produced two of the biggest sports betting personalities in the world: Dave Portnoy and Bill Simmons.

Portnoy, a Swampscott native, is the founder and president of Barstool Sports. Simmons, from Marlborough, is an ex-ESPN star and the founder of The Ringer. So, it begs the question: which Boston-area native is the sports-betting G.O.A.T.?

Sports betting in Massachusetts is still illegal, but that soon could change. A conference committee must iron out differences between Senate and House versions of a sports betting bill before the legislative session ends July 31. There’s no question voters in Massachusetts want sports betting. Just as there’s no question Boston is a major sports city.

Boston is a great sports city

Some of the greatest sports moments in history have involved Boston/New England area teams. Whether it was the 2004 American League Championship Series comeback by the Red Sox or the game-clinching endzone interception by Malcolm Butler in Super Bowl XLIX, there’s no doubting the fact. Without sports, Boston would not be Boston.

Boston teams have won 12 championships since 2000, causing fandom to percolate throughout the entire New England area. Boston has become the modicum of sports success. If you think that success stops on the court, field or rink, then you don’t know Beantown.

From humble beginnings to the Barstool

Long before Dave Portnoy was eating pizza or interviewing the president of the US, he was walking the streets of Boston handing out newspapers. Literally. 

Barstool Sports started out as a newspaper in 2003. Portnoy said of the time:

“I hated my job and I wanted to find something I liked doing, and I gambled. So the paper was really hardcore sports, hardcore gambling, fantasy football – and I would hand it out outside subways in Boston.”

Barstool slowly yet surely grew a dedicated fan base and exploded in 2016, when the Chernin Group purchased Barstool for $10 million. It moved the entire company to New York City, where Barstool continued to grow.

Barstool most recently was purchased by Penn National Gaming for $450 million. Now that’s what you call growth.

Simmons writes his way to The Ringer

Simmons, like Portnoy, started from humble beginnings. In 1997, he launched the website while working as a bartender. Simmons and his website quickly gained steam, and he began writing for Digital City Boston of AOL. The column caught the attention of ESPN, which hired him as a writer in 2001.  

Simmons quickly became one of the most successful writers at ESPN, growing in popularity because of his “everyman” writing style. However, every rose has its thorn. It didn’t take long for Simmons and ESPN to butt heads

Simmons was suspended several times while at ESPN, mostly for criticizing other shows on the network. The final straw came in 2015, when Simmons publicly berated Roger Goodell for the way the NFL handled the Ray Rice situation. 

ESPN, which recently had spent $2 billion to buy the rights to Monday Night Football, obviously had an issue with this. Simmons was suspended, and his contract was not renewed in 2015.

He went on to start his own HBO show and launched the now successful The Ringer in 2015.  Thanks to a bevy of podcasts under The Ringer’s umbrella, Spotify purchased it in 2017 for $200 million

Simmons’ popular podcast now has FanDuel as a title sponsor. The Ringer is a key marketing arm for America’s No. 1 sportsbook.

So which Boston-area native is the sports-betting G.O.A.T.?

Surprisingly, Simmons and Portnoy never really have crossed paths. They work in the same field, are from the same area and share the same “common man” style. Yet, the two remain separated. 

They’re not enemies. In fact, they share a common enemy (ESPN). But where would the fun be if we just let them exist in their own lanes? Let’s take a look at the tale of the tape in the battle for sports betting supremacy.

Tale of the Tape Dave Portnoy Bill Simmons
Twitter followers 2.7 millon 5.6 million
YouTube subscribers 1.15 million (Barstool) 442,000 (The Ringer)
Gambling podcasts/shows 6 1
Sportsbook Barstool Sportsbook FanDuel Sportsbook
Instagram followers 4.1 million 401,000

The verdict: Portnoy reigns supreme

I think it really comes down to three things:

  • Being owned by Penn National Gaming gives Barstool, and Portnoy, the resources to be a bigger influence.
  • Sports betting has been a part of Barstool since the beginning – the Ringer jumped on to the trend when it became hot.
  • Plus, Simmons pushes FanDuel on his podcast while living in California (a non-legal state). This is a bit confusing, at best.

The fact that Portnoy basically has his own sportsbook also pushes the needle further in his direction. Love him or hate him, it’s hard to ignore Portnoy’s effect on the sports gambling world.

Photo by Shutterstock
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Frank Weber

Frank Weber is a US-based gambling writer with a Bachelor’s Degree in Journalism. He loves baseball, football, basketball, soccer, and the UFC, and even collects sports cards and memorabilia in his spare time. In his free time, you could find Frank either out at a concert with friends, or at home sweating out all his bets.

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