Bill Simmons is mere weeks away from launching the most high-profile phase of his professional career — his very own HBO talk show to complement a recently launched website and an already popular podcast. But on this springtime afternoon, the 46-year-old sportswriter turned multimedia juggernaut sits slouched in his Los Angeles office, unable to pull himself out of the past.
Specifically, May 8, 2015, the day the world fell on top of him.
The trouble actually began 24 hours before that. Simmons — part rabble-rouser, part bro whisperer to legions of fans and nearly 5 million Twitter followers who first met him as The Sports Guy — had appeared on Dan Patrick’s syndicated radio show, where he was asked about NFL commissioner Roger Goodell. The subject was radioactive, and Simmons knew it. Just eight months earlier, ESPN had suspended him for three weeks after he blasted Goodell for his mishandling of the Ray Rice domestic abuse scandal. Now, Goodell was threatening to sideline Tom Brady, of Simmons’ beloved New England Patriots, for allegedly conspiring to use underinflated footballs during a playoff game. It would have been out of character for Simmons to hold his tongue, and, to the horror of his longtime network home (which pays nearly $2 billion annually for Monday Night Football), he didn’t disappoint. In another impassioned diatribe, he accused Goodell of, among other things, lacking “testicular fortitude.”
“If you listen to it, it’s a joke,” says Simmons today, his boyish, inquisitive nature matched by his hoodie-and-Converse attire. As he shuttles between his two office buildings at Sunset Gower Studios in Hollywood, where his sports and entertainment empire has been housed since February, he adds, “It’s a wrestling term, and it’s funny.”
The media hadn’t seen the humor, flooding the internet with stories about Simmons’ latest outburst; and neither had his then-boss, ESPN president John Skipper, who forwarded one of the pieces to Simmons’ agent, James Dixon, with a terse note about holding off on contract talks until closer to the September expiration. To this day, Simmons isn’t sure Skipper ever actually listened to the Patrick interview; he didn’t need to, figures Simmons, because at that point the ESPN chief already had several underlings whispering in his ear, “Did you see what Simmons said about Goodell now?” A year removed, the emotions still are palpable. “[Those people] were just trying to cause trouble,” says Simmons. “It was f—ing high school.” (ESPN declined comment for this story.)
Simmons, being Simmons, retaliated in kind, firing off an email that he was pulling out of the network’s upcoming coverage of the NBA draft. Knowing things would escalate from there, he says he had planned to go in the following day and inform the staff at his ESPN-backed media site, Grantland, that the likelihood of him remaining at the company was slim.
He never would get that chance. Simmons woke up the next morning to a New York Times report that his contract would not be renewed. “This is not personal,” Skipper told Richard Sandomir of the Times. “It’s business.” ESPN had decided it would get ahead of the story in an attempt to control the narrative. Simmons, who had been at the company for 14½ years, was blindsided. “It was f—ing shitty,” he says, having caught the news, as many of his employees did, on Twitter. “By the way they handled it, you would think I played grab-ass with some makeup assistant or something.” His rage soon would turn to bitterness, and he never set foot in Grantland‘s downtown Los Angeles offices again.
Publicly, Simmons opted for a strategy few would expect from him: silence. Leaving the Twittersphere to speculate on what had gone down, he and his team immediately got busy lining up his next act. Calls came from every corner of the media universe — Fox, Turner, Hulu, Netflix — as they did from Silicon Valley. “Guys from Google, Yahoo, Twitter, Snapchat,” says Dixon, “these first-rate technology giants were all trying to figure out how to get into the Bill Simmons business.” Some wanted to produce his next project; others simply wanted to invest in him. What he offers — a combination of cross-disciplinary skills, a fiercely loyal fan base and a proven knack for attracting top-level talent — makes him a hugely valuable commodity in the digital age. With his head still spinning, he took calls, meetings and meals. There was a dinner in Beverly Hills with Yahoo CEO Marissa Mayer — who tried to recruit him to run Yahoo Sports and do Katie Couric-style interviews for her site — and a sit-down with Showtime president David Nevins and his boss, CBS Corp. president and CEO Leslie Moonves.
None of the proposals was as appealing as HBO’s, however. The premium cable network would offer him not only a weekly 10 p.m. talk show but also an opportunity to create or consult on other programming for the network and its digital offshoot, HBO Now. Simmons’ podcasts could become TV shows (The Watch already has spawned a Game of Thrones aftershow); and his ferocious stream of ideas for documentaries would be heard as the network looked to regain a foothold in sports. Additionally, HBO — which, two sources say, is paying him between $7 million and $9 million a year, a nice boost from the $5 million he made at ESPN — would agree to be a minority investor in the Bill Simmons Media Group, home to a burgeoning podcast network and media site The Ringer, which launched June 1 with many of the same bylines that propelled Grantland before it was shuttered by ESPN in October.
For the time being, Simmons has taken no other outside investment, using what insiders describe as seven-figure revenue generated primarily by sponsorship and branding deals to help fund The Ringer side of the enterprise. “I had all of these people who wanted to [invest,] famous f—ing people,” says Simmons. “But one of my goals was to have as few people in my life as possible who would be like, ‘Why are you doing that? What’s going on here?’ ” Looking ahead, he and Eric Weinberger, whom he recruited from the NFL Network to run the company, won’t rule out taking on additional investors.
For Michael Lombardo, HBO’s recently departed president of programming who will maintain involvement in Simmons’ talk show, the decision to go after the former ESPN personality was easy. In Lombardo’s estimation, Simmons is tailor-made for the HBO Now era, and his unfiltered take on sports is something to be celebrated rather than feared at a network that doesn’t rely on advertisers or NFL game coverage. “We have a lot more latitude than ESPN has in what’s too provocative, and we present ourselves differently in that we’re point-of-view television. If you don’t like it, don’t watch it,” he says, noting that Simmons wouldn’t be the first firebrand on HBO’s payroll. “We’ve had 13 years of Bill Maher,” Lombardo adds with a laugh. “Trust me, we have gotten plenty of letters over the years.”
On June 22, his reign at HBO will formally begin with the launch of Any Given Wednesday with Bill Simmons. “It’ll be conversations about sports, culture and technology,” he says, “and then me being a snarky asshole.” The format — a mix of his hard takes and interviews — is subject to change, particularly as its host gets more comfortable with the role of television personality. That there’s a subset of the sports press that suggests the latter may never happen — that Simmons isn’t cut out for TV — only appears to motivate him. “Competitive Bill is definitely fired up about that,” he says, seemingly driven by the same “nobody believed in us” theory that’s fueled so many of his favorite sports narratives. “I know how these things go and how easily you can fail,” he adds. “But I really think this has a chance.”
Simmons’ encyclopedic command of sports and pop culture is the product of a childhood largely spent entertaining himself. His social worker mom and school administrator dad split up by the time he was 9. “Anywhere from, like, 8 to 13 is the danger zone,” says the only child. “You blame yourself and all that.”
He remained with his father in the Boston suburbs — “It was right after Kramer vs. Kramer came out, and we were the real Kramer vs. Kramer,” he jokes — before being uprooted to Connecticut with his mother and stepfather as a young teen. Despite the move, Simmons, now married with two kids of his own, never relinquished his identity as a Boston sports loyalist.
It wasn’t until he arrived at Holy Cross in 1988, however, that Simmons would earn the kind of attention he’d come to thrive on. As his college buddy Joe House recalls, he quickly established himself as a ringleader on the Worcester, Mass., campus. A few days into his freshman year, Simmons and another pal were going door to door doling out nicknames to everyone in their hall. He dubbed himself Iceman, a nod to Top Gun, and the friend, Goose. Simmons also launched a satirical newsletter, The Velvet Edge, to document all that was happening in the dorm and rarely went far without his video camera.
“Bill has always been this galvanizing force,” says House, now a Washington, D.C.-based consultant who moonlights as a personality on the Bill Simmons Podcast Network, or BSPN as it’s known in Simmons’ circle. “But he’s an only child and there was also a bit of sharp elbows,” he adds, “so a decent number of people thought he was a prick.”
Fortunately for Simmons, many of those early detractors would come around once his column for the college paper began gaining traction. Even then, he had a knack for making sports broadly accessible, elevating the fan’s perspective to a fine art. He wrote both with humor and a strong point of view. Adds House, “People began to see Bill’s talent, and it helped smooth over how they felt about him, because the column was funny — he was funny.”
After graduation, Simmons moved back to Boston, earned a master’s degree in journalism from Boston University and landed a low-level gig covering sports for the Herald. But he grew almost immediately impatient with the hierarchy of the business, and the time required to get ahead. At one point, he quit writing altogether and tended bar, only to jump back in as the Boston Sports Guy columnist for AOL. Over time, his discursive, pop culture-infused columns drew a cultlike following, with one in which he eviscerated the 2001 ESPY Awards — a “TV holocaust,” he wrote — catching the host network’s attention. John Walsh, then a top ESPN executive, reached out and offered him his first shot at a national platform.
Over the next 14-plus years, Simmons, with the backing of the billion-dollar cable behemoth, became the most prominent sportswriter in America. In addition to his columns, which at their height attracted more than 1 million readers, he churned out two best-selling books (a memoir of Red Sox fandom and a lengthy treatise on basketball), co-created ESPN’s acclaimed 30 for 30 documentary series, launched the popular B.S. Report podcast and birthed his first prestige media site, Grantland, which earned three National Magazine Award nominations before ESPN shut it down. In that time, he also established close relationships with Skipper and his boss, Disney CEO Bob Iger, which ruffled feathers at the network’s Bristol, Conn., headquarters, and built a fervent fan base that included, among others, President Obama, who was interviewed on his podcast in 2012.
But as Simmons’ profile grew, so did his ego and propensity to fly off the handle when things didn’t go his way. One of the more colorful incidents occurred when ESPN killed the first podcast interview Simmons had lined up with Obama in 2008 — per company policy, candidate interviews were off-limits until after the nominating conventions — and then signed off on his rival, Rick Reilly, picking a fantasy football team with the then-presidential candidate for a column a few months later. “I was f—ing mad,” says Simmons, revealing how he retaliated by turning in a lengthy column of pure fiction about picking a fantasy team with John McCain. “I knew they wouldn’t run it,” he adds with a mischievous smile, “and that’s when it really got acrimonious.”
All of that would seem like mere child’s play compared to what went down in the fall of 2014.
Roger Goodell “is lying,” Simmons’ now-infamous rant began. A few days earlier, on Sept. 19, 2014, the commissioner had fielded questions about the league’s investigation of Ray Rice at a press conference in New York. “If you put him up on a lie detector test, that guy would fail,” Simmons continued. “And for all these people to pretend they didn’t know is such f—ing bullshit.” Later in the podcast, he dared someone — anyone — to come after him. “Please call me and say I’m in trouble. I dare you.”
Two days later, his employer accepted the dare, suspending him for three weeks without pay.
Simmons willingly admits he didn’t bother listening to the podcast before it went up and would have edited out the offending part if he had. “If I’d heard it, I would’ve been like, ‘Shit, we should soften that,’ ” he says now. “I just said it wrong. I was basically saying, ‘If the NFL wants to come after me …’ But it sounded like I was challenging ESPN, which was just stupid, and there’s no reason to do that.” He pauses, then adds: “It probably happened for a reason. If it hadn’t been that, it would’ve been something else.”
By early 2015, his situation at ESPN had become untenable. He had largely stopped his involvement with the 30 for 30 doc series and no longer was appearing on ESPN’s NBA Countdown, instead focusing on his insular fiefdom of Grantland and the podcast. “I started to feel like I was Mel Gibson in Conspiracy Theory,” Simmons says with a chuckle. He had a long and growing list of grievances — he needed more resources at Grantland; his podcast wasn’t being properly monetized; his Grantland Basketball Hour was getting bounced all over the schedule — and he wasn’t shy about sharing them. But at that point, he felt he no longer had the ear of Skipper, whom he believes began distancing himself in fall 2013, when a widely read Deadspin story suggested Simmons had become the network’s “shadow president.”
The characterization, which set off alarm bells on both coasts, came on the heels of Magic Johnson’s abrupt departure from Countdown, which the piece reported was the result of a power struggle between Simmons and Johnson. Simmons vehemently denies that accusation, insisting that Johnson left, in large part, because of ESPN’s mishandling of Michael Wilbon, a former Countdown co-host and close Johnson pal, on the show. That it was being positioned any other way set Simmons off. “I was f—ing furious,” he says. “I was yelling at everybody. I was like, ‘What the f—? You guys f—ed this up. Why am I in this?’ And I just made it worse. I should’ve just not said anything and used that to my advantage for the next thing.”
Simmons is all but certain that a few bitter folks in Bristol had planted the story. “That was the first time I really realized, ‘Oh, people at ESPN really resent my relationship with Skipper,’ ” he says. “I read that, and I was like, ‘Ugh, we’re never gonna be the same.’ And I was right: We never were.”
The first approach from HBO couldn’t have come at a better time. It was March 2015, and Lombardo was eager to meet Simmons. He’s no sports fan, but he’d heard two installments of Simmons’ B.S. Report podcast — an interview with Oklahoma City Thunder forward Serge Ibaka and another with Girls creator-star Lena Dunham — and was sufficiently impressed. “I just thought, ‘This guy can go from Lena to Serge Ibaka with such passion and dexterity, I have to meet him,’ ” says Lombardo. The pair talked for close to two hours in the executive’s Santa Monica office. “It was like being in a super-unhappy marriage and then just meeting someone at the grocery story and being like, ‘Oh, that girl’s cool. I could date that person,’ ” says Simmons. He walked out and shot a note to Dixon: “I’m gonna work for HBO, that’s how this is going to play out.”
Not two months later, Lombardo was en route to the airport when a New York Times news alert popped up on his phone: Simmons soon would be a free agent. He shot over an email immediately: “I said, ‘I’m so f—ing sorry this happened this way.’ Whatever happened, it was a fairly inartful, inelegant way for him to be exiting, and I said, ‘I’d love to meet with you as soon as possible.’ ” By late May, Simmons was sitting with Lombardo and HBO chief executive Richard Plepler for dinner on the rooftop at the Peninsula hotel in Beverly Hills agreeing on the shape of his deal.
With the TV piece in place, Simmons took the summer off to regroup. His family rented a place in Malibu, and while his two kids were off at camp, he’d wander the beach reflecting on all that had happened. “I’m not blameless,” he says now, acknowledging: “I acted like a brat a couple times, and there are things I could have handled better.” ESPN insiders suggest Skipper simply had reached his breaking point — after all those years of empowering and defending Simmons internally, he no longer could tolerate the disrespect. But Simmons had a hard time accepting that. He not only was angry but genuinely hurt. “It was always this very emotional relationship,” says Dixon. “Bill’s such a passionate guy, and he viewed those execs as his mentors and champions.”
Even now, the wounds still can feel fresh. As he winds his black BMW through L.A.’s Hancock Park this spring, our conversation about The Ringer quickly morphs into one about Grantland. “The way they handled that to me is the story that hasn’t been written,” he begins, seizing another opportunity to rip his former boss for his November comments to Vanity Fair. For the first and only time, Skipper addressed his decision to fold Grantland in the wake of a staff exodus, which included four key staffers following their former leader. (Twenty more Grantland alums since have joined Simmons’ new company, which counts about 100 employees between the site and show.) “We lacked a full understanding of the bonding nature between Bill and those guys,” Skipper said at the time. Half a year later, Simmons remains stunned by the remark. “Do you understand how dumb that is?” he says now. “I hired every single person who worked for me, it was my idea, and everything we did came out of all the relationships that I had with those people.”
And then, as though still trying to settle the score, he adds of the recent rash of ESPN departures, which include Keith Olbermann and Jason Whitlock: “They’ve now gotten rid of everybody who is a little off the beaten path. Ask yourself this: ‘Who would work there that you respect right now?’ “
Simmons paces the sidelines of his 11-year-old daughter’s soccer game on an afternoon in mid-May, as his wife, known to Simmons’ readers as the Sports Gal, and their younger son stand cheering nearby. Zoe Simmons is a head taller than several on the team and a stronger athlete than nearly all of them. “I love coming to watch her,” he says, as she boots the soccer ball across the Culver City field.
“One of the ironies of my life is that I was definitely a chauvinist with men’s and women’s sports before. I’d always make WNBA jokes and stuff like that. And now I’m like a feminist, and it’s all because of her,” he says, as his ponytailed daughter waves at him between plays. “In L.A., they have all these academy teams for boys, and the girls are treated like second-class citizens. The fields we have are worse than the boys’, too. It all just drives me f—ing crazy.”
In his office a week later, he spins through his wish list for Any Given Wednesday guests, awarding the top spot to Michelle Obama in part because girls’ sports is a subject he’d love to dive into with her. “I couldn’t get her on my podcast, but maybe I could get her on this because it’s HBO,” he says, having already rattled off a few other hoped-for guests, including the Patriots’ famously press-averse coach Bill Belichick and fellow Bostonians Matt Damon and Ben Affleck. “I know by episode four I’ll probably end up with the fifth lead on some CW sitcom, but for now I’m dreaming big.”
In recent months, Lombardo has been urging Simmons to stop stressing over that guest list. “I just keep saying, ‘That’s not why anybody is going to tune in,’ ” says Lombardo, hopeful that Simmons won’t get caught up in the booking wars for A-list talent that consume so many of the other talk shows on the air. “I go back to my Serge Ibaka reference point: He’s not a household name, he’s not Stephen Curry or LeBron James, yet it was a dazzling interview that only Bill can do.”
Lombardo also is the one who convinced Simmons to do Any Given Wednesday at 30 minutes rather than a full hour — “Start with less, you can always grow,” he advised — and to insert more of himself into the show. The plan at launch is to open with Simmons offering a hard angle on an of-the-moment sports or pop culture subject (if the series had been airing in mid-May, for example, the segment would have centered on then-prominent Kevin Durant trade rumors) before moving on to the two interviews and a sign-off that he’s keeping under wraps.
The show’s first interview segment will feature two guests on a given topic — he’s been toying with such pairings as Mark Cuban and Vice’s Shane Smith on how successful people become overextended, or Tony Romo and Aaron Rodgers on the degree of difficulty of the quarterback position — while the second will focus on just one guest, ideally from the world of sports, tech or Hollywood. Simmons envisions running each at about 10 to 12 minutes, though he intends to tape them much longer the day before in a bid to get the most out of his guests. Citing Howard Stern and Charlie Rose as role models, he says of his conversations, “I want them to feel like a podcast.”
Simmons had to convince HBO to let him do the show taped rather than run it live and not in front of a studio audience. His argument was simple: He’s not a performer or a stand-up, and he’ll be considerably more comfortable if it’s just him and his guests, as it has been on his podcasts. Describe the series as a “late-night” show in his presence, and he shudders. “Mine’s at 10,” he says. When it’s suggested that 10 p.m. classifies as late night, he shakes his head, “Nah.” And then, “You feel like it competes with [Jimmy] Kimmel and those guys?” Clearly, Simmons doesn’t — and doesn’t want others to, either. “Those guys are performers, and I’m not. That’s one of the things that we’ve tried to figure out with this show: how to take advantage of things I’m good at and avoid things I’m not.”
When pressed, he clarifies: “I have good taste, I’m really creative, and I’m good at interviewing people. What I’m not good at is doing what [John] Oliver does. That’s a performance piece.” Less concerning to Simmons is his relative inexperience in television and those pesky claims that he’s not as strong on-air as he is on the page. Instead, he suggests he hasn’t gotten a fair shake on TV. NBA Countdown, on which he spent two seasons and is most often judged, never was the show he wanted it to be, much less the show he says he was assured it would be. “They’ve had Countdown for 15 years, and it’s never been good,” says Simmons. “It fails every year, and still people were like, ‘Oh, [Bill] can’t do TV.’ Well, nobody has ever been good on that show.”
Any lack of TV polish didn’t deter Stuart Miller, however, a longtime Simmons fan who’s coming over to run Any Given Wednesday after more than a decade at The Daily Show. Instead, he saw in Simmons something that can’t be as easily taught: “Both Bill and Jon Stewart have really strong points of view, and that supersedes everything,” says Miller. “It doesn’t matter how many years you might have in front of a camera, if you have a great, strong take on things, which Bill obviously does, that’s what matters. Everything else will fall into place.”
But as the June 22 debut of Any Given Wednesday looms, Simmons often is reminded of the lead-up to Kimmel’s late-night launch on ABC 13 years earlier. The host had lured Simmons, then a rising ESPN columnist, to Los Angeles in late 2002 to write on the first season of his show. His role was somewhat nebulous because he didn’t have the comedy chops or the television experience of others in the room; but Kimmel, with whom he’s remained tight, says he enjoyed having Simmons and his outsider’s perspective around. Those early days were famously rocky — “It was the closest thing to drowning without actually being in water,” jokes Kimmel — and the ground-floor view Simmons was provided would stick with him all these years later.
“I knew nothing, but I remember going, ‘Man, this is fast,’ because all of a sudden we were on the air, and Jimmy had a lot to prove,” he says, and then he pauses. Those piercing blue eyes look away, and suddenly the conversation no longer is about Jimmy. Under his breath, Simmons adds, “He had a lot to prove.”
Bill Simmons’ Bench
Eric Weinberger, President, Bill Simmons Media Group
Simmons recruited him from the NFL Network to build his business with COO Geoff Chow. It’s key that all parts work in unison, says Weinberger: “We have a few creative meetings a week where if you were a martian who landed on the planet, you wouldn’t know who works for the show, the site or the podcast.”
Stuart Miller, EP, HBO’s Any Given Wednesday
After spending more than a decade at The Daily Show With Jon Stewart, Miller relocated to L.A. in early 2016 to run Simmons’ talk show. “I’m a huge sports fan,” he says of taking the new gig, “and a huge Bill Simmons fan.” The first Any Given Wednesday test show took place May 31, with a few more scheduled ahead of the series’ June 22 debut.
Sean Fennessey, Editor, The Ringer
“After Bill left Grantland, there was a question of like, ‘What’s the mission supposed to be now?’ ” says Fennessey, who turned down an offer to run Grantland and joined The Ringer. Twenty-three alumni have followed. A much smaller faction, with whom there’s said to be tension relating to the veil of secrecy surrounding the initial staff exodus, moved to MTV.
Joe House, College buddy/podcast personality
Simmons’ inner circle hasn’t changed much since college, where he met buddies House and JackO. In the two decades since, he’s turned both men into popular podcast personalities. “It’s a testament to Bill’s loyalty,” says House, “and his power to recognize that friends having a conversation about sports would be something that people would like to hear.”
James Dixon, Agent
His longtime agent, who also reps Jimmy Kimmel, Stephen Colbert and Jon Stewart (whom he had meet with Simmons in September 2015), went into overdrive in spring 2015 lining up Simmons’ next act. “My phone was ringing off the hook,” says Dixon. Simmons’ PR rep since 2009, Lewis Kay, had the less glamorous job of cleaning up the post-ESPN debris.
This story first appeared in the June 17 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.