The following is an excerpt taken from the new book “How the Jester Became King: Dave Portnoy and the Real Unauthorized Story of Barstool Sports.” by Charlie Stanton (Post Hill Press, December 2024)
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October 2003
Dave was sweaty and beyond exhausted as he bent down to drop off a stack of newspapers next to his bin at the Alewife T-Station in Cambridge. Sporting his questionable goatee and a beat-up Red Sox hat, his skin reeked of the cigar he had smoked inside his maroon 1992 Plymouth minivan while he trudged from station to station. His breath was a mix of tobacco and the hot Italian beef sandwich he’d ordered in between stops. Portnoy needed a shower. As he leaned over to fill the bin, he paused. The sound of fabric ripping echoed across the brown quarry tiles that lined the floors and walls of the subway entrance. Commuters turned their heads at the noise, and their eyes fixated on Portnoy. He knew immediately what had happened:
“It might as well have been like a gunshot went off in Alewife Station. Everybody in Alewife and maybe all of Cambridge just froze. And I was reduced to doing the ‘Oh my god did I just split my pants?’ maneuver. This, of course, is when you have a glazed expression over your face as you feel your ass to see what the damage is. Honestly, it was like time froze for a couple minutes.”
It was an unseasonably warm fall afternoon, just a few months after Mike Portnoy had given his son his $25,000 blessing. Dave, who had quit his sales job and moved back home with his parents to save money, was now spending it hand-delivering his newspapers to more than 100 Barstool Sports bins he had placed around Boston — a job that made grad school look like Margaritaville.
After all of his bins were filled, Portnoy would begin handing out his newspapers to the public, aggressively. The streets of Boston weren’t for the faint of heart. “When we upgraded from black and white to color copies, I would be just screaming things like ‘We got color now! We’re so much better than these other (papers)!’ Whatever the hook was.” Like a vendor peddling overpriced beer at nearby Fenway Park, Portnoy would yell at – borderline berate – commuters to take a copy.
Portnoy was on his own when it came to distribution following Barstool’s first issue on August 27, 2003, when the temp company Labor Ready he hired to help him sent him mostly drifters, half of whom didn’t show up. “Let’s just say they weren’t the most dedicated workers to ever come down the pike,” Portnoy explained. And according to Portnoy, the outfit in Atlanta where he bought newspaper bins, Go Plastics, wasn’t able to deliver the bins on time for the day of the launch, which only compounded this calamity. Most commuters were unable to find Portnoy’s newspapers, as Barstool Sports sat inconspicuously inside plastic bags next to other competitors’ fully marked bins.
Of the 40 train stations where workers were supposed to hand out copies of Dave’s paper that day, only about 15 operated as planned. Portnoy would eventually hire local models to hand out his papers, which, to no surprise, worked better but were too expensive to continue with. “Chaotic and nearly disastrous,” is how Dave described his paper’s first days in existence. Unbeknownst to Portnoy, it was a phrase that would become the narrative of Barstool’s entire operation for the next 20 years.
At the start of Portnoy’s maiden voyage, he was able to produce several thousand copies of his weekly newspaper. This was dwarfed by the daily circulation of the 450,000 newspapers The Boston Globe printed, and the 300,000 distributed by both The Boston Herald and Metro Boston, the city’s largest free paper. But eventually Barstool would reach a peak of 40,000 issues every other week, which was on par with most other alt-weekly publications such as The Phoenix or The Improper Bostonian. Reaching this number was an unlikely development to everyone around Dave in those early days, including his production manager Erin Boyce.
Boyce worked at The Daily Item of Lynn, a neighboring town’s paper; she had extensive experience inside the publishing industry and agreed to help Portnoy after connecting through a friend of a friend. “I really only thought it would last six, maybe 12 issues. I’ve been in the newspaper industry for many years, and to start a publication in a dying industry is kind of unheard of. Little did I know 200 issues later, it would become part of my life for almost nine years.”
Boyce’s help was invaluable, but there was no doubt the 26-year-old was doing the work of five people just to produce the meager eight-page publication. Originally, Portnoy published his newspaper once a week. Mondays were the busiest in terms of writing, and Dave often stayed up past 2 a.m. finishing the last articles for that week’s issue. Tuesdays, Portnoy took his work over to the nearby graphic designer, who worked with Boyce to lay out the paper. Later that day, the layout was taken to Boyce’s printer, and once the thousands of copies were printed, Portnoy filled up his beaten-down minivan to the brim. “When I pick up Barstool Sports from our printer company, I swear I can hear her scream. I actually think the bottom of the car scrapes against the cement when it is fully loaded.”
Wednesdays started at 4:30 a.m. Portnoy made the 45-minute drive south down Route 1A to Boston, dropping his publication off at the bins he had placed inside various T-stations. “I had bins at T-stops I didn’t know existed before that,” Portnoy said of his paper route. He also stopped at select stores, bars, and restaurants he somehow convinced to take his newspapers, like the Grand Canal bar near The Boston Garden or Bayview Liquors in Southie.
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After emptying his van around 9:00 a.m., Dave headed to a T station and handed out copies of Barstool Sports to commuters. Around noon, he drove back to Swampscott to write; call potential advertisers (the paper had fake ones and real ones); or fix whatever part of the business was melting down that day. Around 4:00 p.m., he drove back into Boston to hand out papers again until returning home, well after dinner.
As for the rest of the week, Thursday was a repeat of Wednesday, while Friday, Saturday, and Sunday were reserved for writing. And Portnoy would spend each Monday just like the previous one, cramming in last-minute changes until the candle was burned at both ends. Unsurprisingly, this routine began taking a toll on his health, but as 2004 approached, people slowly began to read Portnoy’s paper. “It was always a good reception and when I judged it, it would be 10 people who took the paper and said they enjoyed it the first time I did it. The next issue would be 20 people, and the next issue would be 40, and the next 80. So, it always was slowly growing and there was something in my gut that was like I’m on to something here.”
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This excerpt is taken from “How the Jester Became King: Dave Portnoy and the Real Unauthorized Story of Barstool Sports.” by Charlie Stanton. Published by permission of Post Hill Press.
Charlie Stanton currently resides in New York City. Stanton graduated from Wake Forest University with Honors in Economics in 2012. In his free time, the author enjoys playing pickleball, paddle, tennis, running, skiing, and spending time with his three younger brothers.
The views expressed in this book excerpt are those of the author and do not necessarily represent those of the Daily Wire.
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