Bill Simmons: The New Journalism Tradition in the Internet Age

The Hunter S. Thompson of online journalism


On the 174th episode of his podcast recorded last January, Bill Simmons interviewed NBA star Kevin Durant in the back of an “undisclosed” restaurant in San Francisco at midnight. “It looks like we’re in a scene from Goodfellas right now,”[1] Durant says, drawing a low chuckle from the Sports Guy at the beginning of an audio stream clocking in at one hour, 16 minutes, and 44 seconds, loaded by millions of fans worldwide on Soundcloud, Itunes, and Sticher.[2] A live version of Pearl Jam’s “Corduroy” fades amidst the clinks of silverware and distant voices of nameless employees and patrons. Mildly distracting background noise is appropriate ambiance for Simmons’ longtime appeal: the perfect unprofessional sports journalist who can shoot the shit with Barack Obama[3] or Al Michaels as genuinely as he can with friends like Joe House[4] or Cousin Sal[5] — about virtually any pop culture or sports subject from Boogie Nights[6] to fast food restaurants.[7]

If you don’t know who Bill Simmons is, consider this: he was smoking “too much” weed and bartending in 1995[8]. Just ten years later, Warren St. John, in The New York Times, writing up his impact on journalism: “Writing from the perspective of an unabashed partisan — his teams are the Patriots, Red Sox and Celtics — he has pioneered an intensely personal style of sports writing that draws on frequent references to movies, television sitcoms, music, video games, even his friends and wife (the Sports Gal of course), always with a side dish of mortar-thick sports history and analysis.”[9] Before he turned 40, Simmons was the most popular sports journalist in America. Now at 47, he’s thriving on his new site, The Ringer, and interviewing a hard-to-book NBA superstar on his massively popular podcast.

Durant, 27, who by Simmons’ measure was already “one of the 22[10] best players of all-time”[11], was caught up in a “media narrative”[12] stemming from his decision to sign with the 73-win Golden State Warriors in unrestricted free agency, spurning his relationship with Oklahoma City and his friendship with longtime teammate Russell Westbrook. “Have you spoken to Westbrook?” and “What will it be like going back to OKC” became the central off-the-court concerns of the mainstream sports media, only fueled by the suddenness of Durant’s departure and vague claims that the media was — once again — making something out of nothing.[13]

Simmons was there to benefit from Durant’s annoyance with the media, just as he has for years — by doing what he would anyway — talking to Durant as a basketball fan and as a real guy, as his own character. Simmons can’t even introduce his sponsors without the occasional joke or vivid personal reference every few podcasts, such as how his wife loves the lipstick on the underwear he purchased from MeUndies[14]. “But first, Pearl Jam,”[15] he says to transition from the sponsors to the interview as if Eddie Vedder were sitting there across from him riffing away. On the 201st episode of his podcast released Thursday, April 20th, 2017, Simmons spent a few extra minutes to announce that The Bill Simmons Show — through 200 episodes — had 100 million downloads.[16]

By traditional journalistic standards, Simmons is the ultimate unprofessional– a historic, positive trait in the eyes of millions of fans. He’s built his career on not putting up the cliché, journalistic wall with the guest or the audience anywhere in his own commentary — written or spoken. In every interview, he unintentionally follows simple instructions laid out by Tom Wolfe’s New Journalism Manifesto in 1972: “talk to him about his thoughts and emotions, along with everything else. This was what Gay Talese did in order to write Honor Thy Father.”[17]

Simmons, despite his idiosyncrasies personal or professional, is well-regarded as a wildly successful online journalist, a pioneer even, who reached superstardom by penetrating and understanding the sensibilities and hormones of millions of sports lovers by getting into their heads — because he’s one of them. As a journalist, he bleeds his real self out to listeners and readers, becoming his own character in the narrative. A journalist wasn’t interviewing an NBA star; Bill Simmons was talking to Kevin Durant.

But the unprecedented success of the Simmons’ style and persona has very rarely been placed in the appropriate historical context[18]. Simmons, in no small part, is the continuation of the new journalism movement in the internet age. The new journalism movement is marked by writers such as Tom Wolfe, Truman Capote, Gay Talese, and Hunter S. Thompson, who, all broke from traditional journalism to inject nonfiction narrative elements into their writing. Often times, as Thompson epitomized, this entailed appearing as a first-person figure within the story. But these hot shots were not simply talented narrative writers, they were celebrities who fundamentally changed journalism for the next 60 years.[19] Bill Simmons has embodied their style and celebrity since he was at “The Boston Sports Guy” on AOL in 1997.

Aided by an early obsession with the Boston Celtics and the sports narrative tradition of David Halberstam’s Breaks of the Game, Bill Simmons has unintentionally become the internet era’s Hunter S. Thompson, bringing gonzo to sports media and revitalizing the tradition of The New Journalism Movement. Simmons’ sports fan gonzo has been fully realized for years, and like the new journalism celebrities before him, Simmons continues to write as a character and a rebel.


Born in Marlborough, Massachusetts, Simmons grew up attending Celtics games after his father bought $200 season tickets five rows behind the visitor’s bench in the TD Garden in 1973. Bill was 4 years old.[20] His father never let him live it down for sleeping through key sequences of game 5 of the 1976 Finals: “My father still makes fun of me about this. In my defense, I was six. In his defense, it was the most famous game ever played.”[21]

Little beliefs and trademarks have emerged in his books and columns (and podcasts) that speak to the wider portrait of his “writing for the fan” style, and the character of Bill Simmons; his reverence of small forward Larry Bird as the leader of “the greatest team ever”[22], or the belief that Bill Russell was the greatest winner ever and better than Wilt Chamberlain on the all-time list are among two of the most common Simmonian creeds. Today, he can rationalize this and dozens more of his wide-ranging, uncompromising opinions, Celtics-related or no, basketball related or not, with an encyclopedic explanation of the best moments — the game, the series, the year. If he weren’t a writer, he’d still be be the biggest basketball fan on the planet.

In his 1997 columns, Simmons began to brainstorm an idea for a Hall of Fame Pyramid that became the centerpiece of The Book of Basketball[23]: a ranking of the 96 best players of all time on a five-level (L4-L5) pyramid.[24] “If we’re building the NBA Hall of Fame from scratch, why not make it…where great players aren’t just elected to the Hall of Fame but elected to a particular level depending on their abilities.” But even just his own “power rankings” similar to what see on ESPN or other sports media did not allow for enough immersion for the fan:

“…head over to the pyramid and by your ticket. They direct you to the second floor of the basement (everyone starts their tour there), where you can find relevant memorabilia from seven NBA decades: old jerseys and exhibits, seats from the old Madison Square Garden, pieces of the parquet from the Boston Garden, all the different basketballs and sneakers, the first 24-second shot clock, the evolution of NBA video games and everything else of that ilk. Consider this the most historical floor of the building. From there, you take the escalator to the top floor of the basement, w ere you find sections devoted to the greatest games and playoff games, as well as plaques to recognize five distinct groups of players.[25] Remember, the goal is to learn everything you and about the history of the NBA, as well as who mattered and what happened.”[26]

The imagination Simmons evinces in the The Book of Basketball is not only a narrative complement to his sports opinions, it has convinced everyone he wasn’t just a nerdy Celtic homer benefiting from the internet’s mass of advanced statistics to back up incessant lists, rankings, what-ifs…he’s never shed his fan-first identity: “I eventually built up enough courage to wander over to Boston’s bench and make small talk with the amused coaches, Tommy Heinsohn[27] and John Killilea…but the time I turned six, you can guess what happened: I considered myself a member of the Boston Celtics. That spawned a racial identity crisis, I gave myself the Muslim name “Jabaal Abdul-Simmons…most NBA players were black.”[28]

Simmons had a head start on obsession, a consistent relationship in his life that would shape his professional career from bartending[29] to married with two kids and running his own media empire. “The Sports Guy” as we know him today may have never lived[30] if he hadn’t started attending Celtics game with his beloved father five rows behind the visitor’s bench[31] in the Boston Garden, literally growing up with moments that make the rounds on ESPN Classic and YouTube, and in his columns.

Simmons further molded his relationship with sports and pop culture into the journalistic sphere through a traditional education, and more importantly, an array of writing influences from David Halberstam to Hunter S. Thompson.

His dramatic rise on the internet is well-documented and extraordinarily influential, but Simmons’ life pre-AOL life as a writer was surprisingly ordinary. A political science major at Holy Cross,[32] he wrote a column called Ramblings for Holy Cross’ school paper, The Crusader. Simmons went on to earn his M.S. in Print Journalism in 1993 at Boston University. According to Mark Kramer, who taught Simmons in his class Writing About Society, Simmons wrote his first piece about a chess player in Harvard Square: “Bill watched, and played, and managed to go off to his lodgings with him, and to hear his life story and record it. He was a well-chosen subject, as anyone who’d wandered through the Square likely remembered him. The piece was so good, it ended up in Yankee Magazine.”

Simmons started working at the Boston Herald as a high school sports reporter, mainly “answering phones… organizing food runs, [and] working on the Sunday football scores section.”[33] Three years later he got a job as a freelancer for Boston Phoenix but was broke within three months and started bartending.[34]

Simmons was an underdog for his style, but never his talents. Kramer observed his brilliance early on: “He was cool, sure of himself, respectful of words and ideas, glad for what he was learning, and was so directed, and so smart, and so socially poised, with a little kidding thrown in, that I was indeed sure then that he was launched and would go far. He hasn’t stopped yet.”

Simmons notes that he had 10–12 writers in his life who had an impact on his writing.[35] He has dropped hints of these influences throughout his columns, but it was David Halberstam who wrote: “the greatest sports book ever.”[36]. Like Simmons, Halberstam was a multi-faceted journalist who wrote about the Vietnam War as well as he did about basketball, and doused Simmons with the life and times of the 1979–1980 Portland Trailblazers in The Breaks of the Game. Johnathan Lethem’s quote on the book helps us understand the general fanfare: “In Jack Ramsay and Kermit Washington and Bill Walton and Maurice Lucas, Halberstam paints characters as good as those in any novel, and they’re entirely unforgettable.” Halberstam followed the team as Wolfe followed druggies in The Electric Kool-Aid Acid Test.

In a 2011 column that later became the preface for Breaks of the Game following Halberstam’s death, Simmons echoed Lethem’s sentiment about Halberstam’s showcased the figures within the Trailblazers organizations — players, coaches, executives — as the real narrative characters and as real people they were, not cogs he observed to forward a reporting plotline. Simmons describes the figures in Breaks of the Game as friends he grew up with — he’s read the book dozens of times since he was a teenager: “I read it every year to remind myself how to write — how to save words, how to construct a sentence, how to tell someone’s life story without relying on quotes, how to make anecdotes come alive…it changed my life for the better.”[37]

For or a journalist intentionally choosing not to hide his glaring Celtics fandom from his writing and commentary[38], Simmons still had to convince media colleagues and audiences that he could be trusted. Lethem characterizes the media world’s sentiment on Simmons’ fandom in his review of The Book of Basketball: “Yet despite…particular biases that I’m sure we’ll all delve into more deeply in the next round, Simmons did strike me as a persuasively passionate, all-senses-tingling advocate for basketball per se. I suspect that if many of his readers are like me — and I suspect many are — he’s capable of reigniting a passion that, despite LeBron, has dimmed considerably in recent years.”[39]

Simmons accomplished this in part through his obsessive dedication to supporting all his claims and creating fantasies like the Hall of Fame pyramid that are the mark of someone who actively wants to promote basketball, as Lethem observes. His approach to sports is that of a nature writer, whose role of a media member seems far removed from their Thoreauian long-form, even if they are writing for a mainstream publication. Writing from the fan’s perspective naturally demanded that he separate himself as much as he could from the brand of the outlet. The air of pride expected in the columns or real-life persona of a typical writer’s employer is not important to Simmons. And even barring his unique relationship with his various employers (namely, of course, ESPN), Simmons never seemed to care for wanting to be known as “The Sports Guy of HBO” any more than “The Sports Guy”.

Simmons took Halberstam’s “fly on the wall” style in Breaks of the Game a step further by inserting himself into his narratives — not only as the kid growing up going to Celtics games, but also as Simmons the rebel journalist, the character who is ever-present in any interview or story or books. He was channeling, directly, the new journalism movement.


There is only one secondary piece of literature that likens Simmons career to that of the new journalists, a 2013 USA Today College article in which the author explains new journalism and its rise on the internet: “By emerging from the back alleys, [Simmons] used the Internet to accomplish something [Hunter S. Thompson] never had the chance to: set a plausible business model for young aspirants to follow…who, like Simmons and Thompson before them, believe journalists can still have a blood-red heart and soul.”[40] There seems to be no other concrete belief that Simmons has, intentionally or unintentionally, carried on Wolfe’s traditions.

Tom Wolfe, the white-suit-wearing author behind the famous essay The Kandy-Kolored Tangerine-Flake Streamline Baby and the somewhat unintentional pioneer of the New Journalism movement[41] exposed his generation’s penchant for bringing narrative form — and the ensuing chaos of the ’60s — to mainstream journalism: “‘The hell with it …let chaos reign …louder music, more wine …All the old traditions are exhausted and no new one is yet established. All bets are off! The odds are canceled! It’s anybody’s ballgame …”[42]

Wolfe’s generation of narrative writers were able to take advantage of the uproarious 1960s, the “whirlpool” as he describes of hippies, black militants, drugs, politics, all of it, since mainstream journalists and novelists alike were leaving a void for long-form, third-person narrative that allowed readers to “get into the heads” of various figures with several literary devices. Chiefly, according to Wolfe’s manifesto, “realistic dialogue involves the reader more completely than any other single device.” Beyond realistic dialogue, Wolfe notes a complicated need to narrate, down to glances, grimaces, tones, and vaguest interactions, all the characteristics of main and supporting figures alike to establish relationships without screaming them at the reader.

Like other writers, Simmons applies Wolfe’s novelistic lessons to journalism as many other sports writers have done. He opened part four of his Red Sox book Now I Can Die in Peace[43] with this descriptive interlude: “We left the seats and headed underneath Fenway, settling on the television situated near the entrance behind home plate. If you haven’t been underneath Fenway, there isn’t a more sinister area in any baseball park — murky, smelly, unhappy, crowded, dank, dungeon-like.”[44]

But Simmons did not follow Wolfe’s “third person narrative” lesson the way Gay Talese did in his famous “Frank Sinatra has a Cold” in any of his books or columns. The most important new journalism influence on Simmons come from a rebel of his own generation, Hunter S. Thompson.

When he was still “The Boston Sports Guy” on AOL, Simmons wrote a few modern-day gonzo pieces, crediting Hunter Thompson for inspiring a running diary piece about his trip to Las Vegas in 1999, a device he used on future vacations.[45] In 2009, Simmons celebrated the 20th season of his East Coast fantasy football league, and a friends 40th birthday party: “He hadn’t embarked on a full-fledged Vegas weekend in eons, a shame because once upon a time there was no better 5 a.m. drinking/smoking/stuttering blackjack wingman than Grady.”[46]

“I should write about this, this would be a funny column,” was Simmons’ logic for first writing about Vegas, and Thompson confirmed a supreme lesson of his long-form: “From Hunter, I learned that anything was possible — as long as it was entertaining, you could write 50,000 words about using a port-o-john and people would read it. That’s a pretty liberating lesson.” Bill repeated the lesson at the 2017 Play It Forward Conference — “If something is good, it doesn’t matter how long it is.”[47]

Word limits represented an aspect of traditional journalism that Bill rejected, a world Hunter S. Thompson rejected de facto with drug use much to the benefit of his professional career. In a 2005 piece following Thompson’s suicide, Simmons painted his professional lesson beyond more than just breaking style rules, but breaking tradition: “When you’re coming up in this business, everyone tells you what you can’t do — you haven’t paid your dues yet, you’re too young, the piece is too long, you need to tone this down, and so on. Hunter was the flip side. He made you think of the things that you could do.”[48]

The running diary idea is the most tangible evidence of Thompson’s influence on Simmons and was not limited to an every-few-years one-off column about Vegas or a humorous one-off about a vacation. Simmons used the “running diary” style for some of the most important columns of his sports fan life, perhaps most importantly, the climax of his first edition Now I Can Die in Peace, a column that originally appeared on ESPN, in the seconds when the Red Sox broke the Curse of the Bambino:[49]

“8:40: “I’m staring at Edgar Renteria right now wondering, “Does this look like the guy who will make the last out when the Red Sox win the World Series?” (You know what? Yes. Yes, he does.)

8:41: “One-hopper back to Foulke, underhand scoop to first…HEE-YAHHHHHHHHHHHHHHHHHHHHHHHHHH!!!!!!!!!!

8:41: “HOLY %%#$@…”[50]

Thompson helped pass along courage for Simmons think outside the box of professional ethics and traditional scales. The new journalism writers had something to break them out of the monotonous drag of being “any other reporter” — for Thompson, it was drugs and revelation that he could drug his way through. For Simmons, it was sports and the internet.

Simmons and then ESPN president John Walsh were planning on making the trip out to Colorado to visit Thompson, but they were too late: “Looking back, if I had a choice between the Red Sox winning the World Series and spending the weekend with Hunter S. Thompson, obviously, I’m going to the Sox. But it’s closer than you would think.”[51]


Simmons the character in his columns and in The Book of Basketball (among other works) does not appeal to all. Lethem, who liked Simmons bestseller in spite of its roaring fandom, found The Sports Guy’s celebrity distracting: “Simmons’s glances at his public reputation were distracting, at best. For instance, there’s too much about how he’s suppressing his Celtics love, which isn’t remotely suppressed. I guess some public shtick established elsewhere was supposed to make me see how Celtic-abnegating he’d been here.”[52] Lethem further criticized Simmons for using some of his column material for the new edition of the book where he was filling in fresh takes and analysis for the 2009–2010 season.

Ultimately, Simmons’ brash, borderline smartass demeanor has not only garnered a massive, multi-generational fan base, it has very directly presented consequences in his professional life and dictated the course of his career in a way that might make Thompson proud.

ESPN scooped up Simmons for the exact reason they fired him 14 years later: smugly assessing their golden-boy corporate culture with his own brand of biting sarcasm and unfiltered fanfare that had made him so successful as the “Boston Sports Guy.”[53] He never altered his style or put the company’s looming obligation to clean-cut Disney standards ahead of his own opinions — of his co-workers, of how the company treated him, and of course, or when he grossly observed The Worldwide Leader in Sports churning out unworthy media narratives.[54]

Simmons garnered attention after his running diary[55] of the ESPYS — Excellence in Sports Performance Yearly Award — was spread around ESPN in Bristol, Connecticut. Simmons carved ESPN’s summer ceremony as a television holocaust: “8:22 — Steve Largent reads the Emmy rules… allegedly a comedy segment. I’ve watched funerals for slain policeman that were packed with more comedy.”[56] Simmons concluded in that 1999 column that “Hell will freeze over before I sit through another ESPYs telecast.” It turns out he would watch the ESPYs again — and write about it in this fashion again — for ESPN. The media giant hired Simmons in 2001 after three guest columns to work for its alternative Page 2, including one titled “Is Clemens the Antichrist?”

Simmons maintained a problems-free relationship with the company until at least 2009. Even as suspensions began, he was enjoying his own corner of sports and pop culture long-form on ESPN owned online magazine, Grantland. For all the drama towards the end of his tenure with ESPN, and the general snarkiness with which he carried himself his 14 years there, it’s often easy to forget the array of positive working and personal relationships Bill Simmons made with writers like Michael Wilbon, Tony Kornheiser, and all the other editors he would recruit to work for Grantland[57]. Simmons also helped create their short documentary series 30 for 30, which went on to win ESPN an Emmy and was widely regarded at their greatest asset. By the time his contract was up, he was asking for six million dollars, a figure that places in a pantheon of journalists’ salaries.

In 2009, Simmons feuded with Boston sports radio station WEEI’s The Big Show, an affiliate of ESPN, with comments about how “they were bullies”, specifically afternoon host, Glenn Ordway. Simmons called into Mike Felger and Tony Massarotti’s rival show on WBZ to dish about The Big Show, and later took to Twitter: “Hey WEEI: You were wrong, I did a Boston interview today. With your competition. Rather give them ratings over deceitful scumbags like you.” The Boston Herald noted that Simmons was only allowed to go on WEEI in the Boston market because of its recent partnership with ESPN, and his Twitter outburst and feud with WEEI landed him a two-week suspension for violating social media guidelines.[58] A later statement of the incident is good evidence of Simmons general attitude towards ESPN and his place in sports media:

“To be honest, I knew the “deceitful scumbag” posting would cause a splash, and I did it intentionally. That’s the same reason I went on this rival radio show. My attitude was, you guys aren’t handling this….this is our alleged partner, and they have on their website that I’m the fraud of the week, and you guys have done nothing. I escalated things intentionally to make them look at it and have meetings about it and fucking waste their day. That made me happy. I’m glad they had two days of meetings about how to handle it because they should have had those meetings two weeks before. I met with Norby[59], who I’d never met before and who I can’t decide if I liked or not. He clearly was trying to intimidate me in the meeting, but I was in a really good mood, and my book had just come out. And in person, I’m not intimidated, and I’m actually like a really happy, gregarious guy. It’s just very hard for people to rattle me. And even when they try, it’s just not going to work. So I think Norby envisioned this as some sort of showdown where he told me, “This is how ESPN works and you’re not playing the game.” It’s like a bad sports movie. And I’m just sitting there with a big smile on my face, like, Oh, it’s great that we finally met, and within five minutes I disarmed him, but he still had to go into the whole “People here don’t think you’re a team player, you think the rules don’t apply to you.” And I said, “I’m actually kind of feeling like maybe they shouldn’t to some degree. Maybe I should be able to get away with more in my column. I’ve been your best guy on the website for nine years. I should have a little more leeway. I’d get that leeway anywhere else.”[60]

With his arrogance and sense of entitlement on full-blast, Simmons detractors are pronounced the way other high-profile sports columnists would never endure beyond run-of-the-mill internet trolls and media haters. Simmons increasingly rejected ESPN’s Disney-bred culture in a way other writers never would, certainly not publicly: “I worry about ESPN becoming too conservative. Although here’s the part I don’t get: how do you explain my book…it has dick jokes and porn jokes in it. It has jokes about how I smoked too much pot in 1995. Sometimes I wonder if they are willing to look the other way unless it ends up in the Sports Business Journal…if it gets there, they know George [Bodenheimer][61] is going to see it.”[62]

The tension was not confined to Twitter or retrospective quotes and comments on The Ringer or his podcasts. Simmons managed tension live — his Achilles’ heel is undoubtedly his presence on television. On NBA Countdown, he seemed continuously amused by the spectacle of talking hoops with Jalen Rose and Magic Johnson. On the 2013 Draft show, he made off-color remarks throughout most of the telecast,[63] and directly responded to NBA Coach Doc Rivers comment that he was “an idiot”.[64].

Even on HBO where he has free rein to say what he wants,[65] his HBO show Any Given Sunday was a rating disaster, barely averaging 200,000 viewers on the first broadcast. Simmons’ typical humor and fandom were plainly there; Ben Affleck went on to exclaim that “Deflate Gate is the ultimate bullshit fucking outrage of sports ever, it’s so fucking stupid that I can’t believe it. You realize they gave him a suspension for a quarter of the regular season.” But for some reason, Simmons writing and podcasting has never translated to broadcast. On television, he appears almost self-mockingly the way Thompson often seemed in interviews. Any Given Sunday was canceled after 18 episodes, a fact that Simmons made fun of (and criticized) on a few podcasts in November and December 2016.


“You have to get them comfortable and saying stuff they didn’t think they were gonna say,” Simmons recently instructed at the 2017 Play It Forward conference at Boston University. For his interview with Kevin Durant on Episode 174, that meant talking basketball — down to the screens and individual chemistry. They discussed details of the Warriors’ offense; how Durant enjoys playing around more playmakers (than he had in Oklahoma City) and more off-ball with a renewed focus on defense. For another journalist, these details might have seemed like pleasant filler building up to a Westbrook question.

“Let’s talk about media narratives,” Bill says at the ten-minute mark, ready to play devil’s advocate to the sports media for the rest of the podcast. “Are you amused that people are so fascinated by you and Westbrook?”

Durant: Yeah, it’s pretty weird to me.

Simmons: That they’re…slow motioning clips during the game to figure out if you looked at him? reiterated, laughing. “I’m tired of hearing about it…wasn’t even gonna ask you about it.

Durant: I’m tired of talking about it cause, look, at the end of the day, I didn’t say anything about that man’s family…I just switched teams, man.

Simmons: You guys will get it back; it’ll happen at some point…you fought too man wars together! You were together for 8, 9 years!

Durant: I’m enjoying myself, you’re enjoying…like who gives a shit!”[66]

And in one fell swoop, Simmons appealed to Durant in a way no other sports journalist really has in years, by challenging the norm of how an athlete should be treated in an interview:

Simmons: You seem really frustrated by that, that people don’t see you as a human.

Durant: I went from being the choir boy in the NBA into just being this…quote un quote, whatever you wanna call me…Every time I say anything about the media, all these guys get really offensive and sensitive, and it’s like, come on man, like, you can say whatever you want about me and I’m supposed to take it, but when I challenge you a bit…

Simmons: I didn’t get mad when you got mad at me at Twitter that time.

Durant: Yeah, cause you’re a real guy! You know what I’m saying?

Simmons: Thanks, man!

A real guy.

Bill Simmons is the most successful online journalists ever, a dreamy benchmark for hapless long-formers craving a chance to showcase their wit in columns riddled with effortless, accessible pop culture references and at the next moment, advanced basketball statistics wrapped up in incandescent nerdism that are celebrated for letting his fandom embarrass the narrative a bit because he knows what were all thinking: “fuck, can someone actually have a real conversation about sports without talking about the drama?”

The journalist isn’t possible without the dude who sat five rows behind the visitor’s bench with his father watching Celtics games. Only Simmons could have put his life’s experiences to the web page in a way that was funny, but also genuine enough to garner listeners and readers by the hundreds of millions.

Under the laissez-faire censorship umbrella of HBO, and at the peak of his career with a new site The Ringer, Simmons is gladly raising the middle finger to the mainstream media higher than he ever has before, and carving out his legacy as New Journalism’s unique gift to the internet, a character in his stories, and a celebrity larger than a journalist who took Hunter S. Thompson’s advice and broke all the rules.

Simmons took a few extra minutes to reciprocate Durant’s compliment: “It’s…one of my favorite podcasts that I’ve done, I think there’s just something different about it, very cool conversation with a guy who just loves hoops, and isn’t afraid to say stuff at this point in his career and is candid in a good way, not gets attention way, and is just a real dude.”[67]

There are lessons to take from Simmons commitment to the new journalism model, and his own, unique character-driven prose that has given his work hundreds of millions of unique readers and listeners. In an era dominated by the scares of “fake news”, mass suspicion of political and social biases, and even the simple accusation of elitism, Simmons stands firm as a journalist so unseparated from the man that no one feels tricked, misled, or uneasy about some hidden agenda. Some media analysts think objectivity is dead. For Simmons, it was never alive. The 22-best basketball player of all-time was interviewed by a weed smoking bartender at a restaurant in San Francisco because they both enjoy basketball.


[1] Bill Simmons, Ep. 174: Kevin Durant — The Bill Simmons Podcast, audio, MP3, 2:3, accessed April 17, 2017.

[2] The three primary music platforms that Simmons uses for his podcast.

[3] During the interim between ESPN and HBO, Simmons interviewed the former president for GQ, and managed to ask Obama about the Chicago Bulls and Game of Thrones

[4] Joe House is Bill’s longtime buddy that — in his own estimation — has continuously benefited from Simmons fame. He’s a podcast regular, a Washington sports fanatic, and has more Twitter followers than Washington Post beat writers.

[5] So called for being Jimmy Kimmel’s cousin, the self-described Italian degenerate gambler has gone on Simmons podcasts to predict over/under betting lines for NFL matchups since the 2007–2008 season.

[6] Simmons and House dedicated a whole podcast to the 1997 film’s top twenty character’s:

[7] A few years later, The Ringer staff produced a comprehensive list of the top 50 fast food items in America, which he and House reacted to in a podcast:

[8] Bill Simmons, The Book of Basketball: The NBA According to The Sports Guy (New York: Ballantine Books, 2010), 4.

[9] Warren St. John, “The Sports Guy Thrives Online,” The New York Times. November 20th, 2015.

[10] The exact rankings are very literal; Simmons constructed, in exhausting detail, the top 96 players of all time in The Book of Basketball.

[11] Bill Simmons, Ep. 173: Steve Kerr — The Bill Simmons Podcast, audio, MP3, 2:2, accessed April 18, 2017.

[12] Simmons own characterization of the Durant-Westbrook saga -

[13] James Herbert, “Warriors’ Kevin Durant says media created ‘feud’ with Russell Westbrook,”, February 8th, 2017.

[14] Bill Simmons, Ep. 197: All-NBA/MVP Tester Ballot with Joe House — The Bill Simmons Podcast, audio, MP3, 23:2, accessed April 17, 2017.

[15] He tweeted them after they approved “Corduroy” — “PS: thanks to @pearljam for our new BS Podcast theme music that comes from their 2016 Wrigley shows.” He couldn’t help himself. It’s like they became part of his family.

[16] Bill Simmons, Ep. 201: NBA — The Bill Simmons Podcast, audio, MP3, 23:2, accessed April 17, 2017.

[17] Tom Wolfe, “Why They Aren’t Writing the Great American Novel Anymore: A treatise on the Varieties of Realistic Experience,” Esquire, Dec. 1972.

[18] A thorough search on the internet turned up exactly one piece from USA College Today playing Bill Simmons (loosely) in the new journalism context

[19] Christopher B. Daly, Covering America: A Narrative History of a Nation’s Journalism. Amherst: University of Massachusetts Press, 2012.

[20] Bill Simmons, The Book of Basketball: The NBA According to The Sports Guys (New York: Ballantine Books, 2010), 4.

[21] Bill Simmons, The Book of Basketball: The NBA According to The Sports Guys (New York: Ballantine Books, 2010), 10.

[22] The 1986 Celtics headlined by Bird in one of his MVP seasons, crafty power forward McHale, and center Robert Parish. Of course, the team also featured a late-career Bill Walton.

[23] First published in 2009 and revised in 2010 with reworked rankings, Simmons has hinted that he will need to put out another edition of the book

[24] The 5th level was called The Pantheon, and like the Greek Gods, reserved for the 12-best players of all-time.

[25] Simmons even carved out separate groups to honor those who couldn’t make his Hall of Fame Pyramid — Group 1: The Pioneers, Group 2: The Harlem Globetrotters and Other African American Pioneers, Group 3: Greatest Role Players, Group 4: The Record Holders, Group 5: The Comets.

[26] Bill Simmons, The Book of Basketball: The NBA According to The Sports Guy (New York: Ballantine Books, 2010), 275.

[27] Years later, Simmons would revere Heinsohn for his longtime commitment to the Celtics (since 1956, #56 on the pyramid), and appreciate his emphatic fandom as the local telecast announcer for the Celtics.

[28] Bill Simmons, The Book of Basketball: The NBA According to The Sports Guys (New York: Ballantine Books, 2010), 4.

[29] When he was smoking “too much” weed.

[30] In The Book of Basketball, Simmons revealed that his father almost got a motorcycle instead: “Maybe you wouldn’t be kicking yourself for spending money on this book right now. Life is strange.

[31] Bill Simmons, The Book of Basketball: The NBA According to The Sports Guys (New York: Ballantine Books, 2010), 4.

[32] The first footnote in his Red Sox book: “Imagine being stuck at an all-male school in 20-degreee weather. Yikes. If you’re scoring at home, Holy Cross finally started admitting women in 1972, although they didn’t start admitting women who put out until 1999.

[33] David Scott, “The Boston Sports Guy: Revisited, Reinvented and Revealed,” Internet Archive Wayback Machine, Sep. 30th, 2005.

[34] “Bill Simmons Influences Curated by,” My

[35] Bill Simmons, “Farewell, Hunter”, ESPN.,

[36] As Simmons wrote in a July 2011 column, “I believe Michael Jordan is the greatest basketball player ever, and I can prove it. I believe The Breaks of the Game is the greatest sports book ever, but I can’t prove it

[37] David Halberstam, The Breaks of the Game, (New York: Ballantine Books, 2010), xii

[38] Warren St. John, “The Sports Guy Thrives Online,” The New York Times. November 20th, 2015.

[39] Jonathan Lethem, “”I felt starved for something booklike in this book-resembling object.” Vulture. December 10th, 2009.

[40] Jarrred Saffren, “Viewpoint: The Bill Simmons model and how the Internet changed journalism,” USA Today College.

[41] Wolfe claims he doesn’t like the term “new journalism”, and Daly notes that John Hersey among other writers had written in this manner before Capote. Wolfe just happened to have written some informal rules.

[42] Tom Wolfe, The New Journalism with an Anthology Edited by Tom Wolfe and E.W. Johnson (New York: Harper and Row, 1973), 4.

[43] The book is a series of columns written from 2002–2009 documenting Simmons’ reaction and reflection of the Red Sox winning the World Series in 2004 and 2007.

[44] Bill Simmons, Now I Can Die in Peace: How the Sports Guy Found Salvation Thanks to the World Championship (Twice!) Red Sox, (New York: ESPN Books, 2009.)

[45] Bill Simmons, “Farewell, Hunter”, ESPN.,

[46] Bill Simmons, “You’re never too old for Vegas.”, ESPN., last modified September 3rd, 2009,

[47] Play it Forward BU, Twitter post, April 14th, 2017, 1:59 p.m.,

[48] Bill Simmons, “Farewell, Hunter”, ESPN.,

[49] The book was republished to account for the 2007 World Series much how The Book of Basketball was for fresh takes on Lebron, Wade, and Bryant.

[50] Bill Simmons, Now I Can Die in Peace: How the Sports Guy Found Salvation Thanks to the World Championship (Twice!) Red Sox, New York: ESPN Books, 2009, 333

[51] Bill Simmons, “Farewell, Hunter”, ESPN.,

[52] Jonathan Lethem, “”I felt starved for something booklike in this book-resembling object.” Vulture.

[53] In true journalistic fashion, ESPN made him drop the “Boston” label from his Sports Guy moniker

[54] He often made fun of First Take, the infamous sports talk show that featured Skip Bayless and Steven A. Smith for the second half of Simmons ESPN tenure.

[55] It seems no coincidence that his Thompson-inspired running diary pieces have occurred at the most major junctures of his life.

[56] Barry Petchesky, “Here’s The AOL Column That Got Bill Simmons Hired By ESPN, In Which He Calls The ESPYs A “TV Holocaust”, Deadspin, January 20th, 2017.

[57] His online magazine was a subsidiary of ESPN was shut down when he left. Many of The Ringer’s editors were senior writers for Grantland, who defected soon after Simmons was fired.

[58] “ESPN’s Bill Simmons Feuding With WEEI-AM’s “The Big Show” Sports Business Daily. November 12th, 2009.

[59] Norby, Williamson, ESPN’s Executive Senior Vice President of Studio and Event Production

[60] A.J. Daulerio, “Bill Simmons, Big Swinging Dick,” Deadspin, last modified May 18th, 2011.

[61] As of January 1, 2012, Bodenheimer was the executive chairman of ESPN, with John Skipper replacing him as president.

[62] James Andrew Miller and Tom Shales, Those Guys Have All the Fun: Inside the World of ESPN. New York: Back Bay Books (Little, Brown, and Company), 2011.

[63] NBA Draft 2013: Doc Rivers’ thoughts on Bill Simmons // Things get awkward on live TV

[64] Simmons believed Rivers had quit on the Celtics at the end of the 2012–2013 season, and should own up to it. (Rivers went on to coach the Los Angeles Clippers the following season).

[65] This is something Simmons had drawn attention to several times — that HBO wouldn’t censor him the way ESPN had for years.

[66] Bill Simmons, Ep. 174: Kevin Durant — The Bill Simmons Podcast, audio, MP3, 40:3, accessed April 17, 2017.

[67] Bill Simmons, Ep. 174: Kevin Durant — The Bill Simmons Podcast, audio, MP3, 1:3, accessed April 17, 2017.