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

Dave Portnoy and Bill Simmons, both hailing from the Boston area, have emerged as two of the most prominent sports betting figures on a global scale.

Portnoy, hailing from Swampscott, holds the title of founder and president at Barstool Sports. Meanwhile, Simmons, a native of Marlborough, is a former ESPN star and the creator of The Ringer. This prompts the inquiry: which Boston local reigns supreme as the greatest of all time in the realm of sports betting?

Currently, sports betting remains illegal in Massachusetts, but there is a possibility of this changing in the near future. Before the legislative session concludes on July 31, a conference committee needs to resolve discrepancies between the Senate and House versions of a sports betting bill. Undoubtedly, Massachusetts residents are eager for the legalization of sports betting, and it is evident that Boston holds a significant position in the realm of sports.

Boston is a great sports city

Boston/New England area teams have been part of some of the most unforgettable sports moments in history. From the remarkable comeback by the Red Sox in the 2004 American League Championship Series to Malcolm Butler’s game-deciding endzone interception in Super Bowl XLIX, there is no denying the impact of these moments. Sports have played a vital role in shaping the identity of Boston, making it the city it is today.

Since 2000, Boston teams have secured an impressive 12 championships, igniting an overwhelming passion for sports across the entire New England region. Boston has undeniably emerged as the epitome of sporting triumph. If you believe this success is confined to the confines of the court, field, or rink, then you clearly underestimate the spirit of Beantown.

From humble beginnings to the Barstool

Before Dave Portnoy indulged in pizza or conducted interviews with the president of the United States, he spent his earlier days strolling through the streets of Boston, distributing newspapers. Quite literally.

In 2003, Barstool Sports originated as a newspaper, as mentioned by Portnoy during that period.

Disliking my job immensely, I yearned to discover an occupation that truly intrigued me. In a daring move, I ventured into the realm of gambling. Consequently, my focus shifted towards creating a fiercely dedicated publication centered around sports, gambling, and fantasy football. I would distribute this paper outside subway stations in Boston.

Barstool’s dedicated fan base grew steadily over time, but it was in 2016 that things really took off when the Chernin Group acquired the company for a whopping $10 million. With the move to New York City, Barstool’s growth only accelerated further.

Penn National Gaming recently purchased Barstool for a whopping $450 million, exemplifying remarkable growth.

Simmons writes his way to The Ringer

Simmons, just like Portnoy, began his journey from modest origins. Back in 1997, he took the leap and created BostonSportsGuy.com while juggling his job as a bartender. With his website taking off at a rapid pace, Simmons’s talent caught the eye of Digital City Boston, an AOL publication, where he started contributing. ESPN eventually noticed his column and in 2001, they offered him a writing position, further propelling his career.

Simmons swiftly rose to prominence as one of ESPN’s most accomplished writers, captivating audiences with his relatable writing style. Nevertheless, no success story is without its challenges, and before long, tensions arose between Simmons and ESPN.

Simmons faced multiple suspensions during his time at ESPN, primarily due to his criticism of other programs on the network. However, his breaking point occurred in 2015 when he openly berated Roger Goodell for the NFL’s handling of the Ray Rice situation.

After ESPN’s hefty $2 billion investment to acquire the Monday Night Football rights, it became evident that they had a problem with Simmons. Consequently, he faced suspension and his contract was not extended in 2015.

Afterward, he proceeded to create his own show on HBO and established the currently thriving The Ringer in 2015. With an array of podcasts falling under The Ringer’s scope, Spotify acquired it in 2017 for a whopping $200 million.

FanDuel is now the title sponsor for Simmons’ highly regarded podcast. The Ringer plays a vital role in promoting America’s top sportsbook.

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

It is quite unexpected that Simmons and Portnoy have never actually met each other. Despite being in the same profession, hailing from the same region, and embracing a similar down-to-earth approach, the two individuals have somehow managed to stay apart.

Although they both have ESPN as a common enemy, they are not enemies themselves. However, it wouldn’t be as entertaining if we simply allowed them to operate independently. So, let’s examine the comparison of their strengths in the competition for dominance in sports betting.

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

In my opinion, it ultimately boils down to three factors.

• Barstool, along with Portnoy, gains a greater ability to exert influence due to its ownership by Penn National Gaming.
• Barstool has incorporated sports betting from the start, while the Ringer hopped on the bandwagon when it gained popularity.
• At best, it is a bit confusing that Simmons promotes FanDuel on his podcast despite living in California, where it is not legally allowed.

Portnoy’s ownership of his own sportsbook undeniably amplifies his influence, regardless of whether one admires or dislikes him. It is impossible to overlook Portnoy’s significant impact on the realm of sports gambling.