From ESPN to HBO, can Bill Simmons liven up ‘Wednesday’?


There’s an old joke that says when considering the distance from the back of an arena to center stage, it’s the last few feet that are the hardest to cross.

Bill Simmons, former popular columnist for ESPN and founder of the departed sports and pop-culture website Grantland, is about to make that leap as host of the new HBO show “Any Given Wednesday,” which premieres, naturally, Wednesday. Advance screeners were unavailable, but we know the series will adhere to something of a talk-show format with a mix of videos, one-on-one interviews and a roundtable segment consistent with its tagline, “the sport of conversation.”

“He provides a very iconoclastic approach to sports and he’s able to do it and draw in a real strong audience and a young demographic,” says Lee Berke, a sports media consultant.


“Wednesday” marks the final step in a journey that began at AOL in the late ’90s when Simmons began writing columns as “The Boston Sports Guy,” which started something akin to a revolution of sportswriting from the fan’s perspective — blind loyalties, irrational hatreds, left-field arguments, pop culture-drunk jokes and all.

The column that got Simmons hired by ESPN called the 1999 ESPYs a “TV holocaust.” Subsequent columns for the sports network’s Page 2 website saw Simmons freely (and entertainingly) mix his pop culture obsessions — “The Wire,” “Hoosiers” and “Rounders,” to name a few — with his sporting ones, which in the early ’00s included a pair of improbable championships for his beloved New England Patriots and Boston Red Sox.

His casual and conversational blend of humor and gut-feeling analysis sounded like nobody else covering sports online. Now entire websites, such as Gawker Media’s Deadspin and Vox Media’s SBNation, have followed in his wake.

But his style is not universally beloved — his critics have grown weary of his homer-ism and his reliance on pop culture ephemera, among other tics — and Simmons has become a divisive figure inside and outside of sports media circles and among its readers and watchers.

“The notion that the world of sports writing was available to you and me, and everybody else, was an entire foreign one on a national level before Simmons,” wrote Deadspin founder Will Leitch in a column last year for the website Sports on Earth. “Every sports column before Simmons was part reporter, part bouncer; we’ll tell you what happened, but from behind this rope line, and you stay where you are. Simmons invited you in.”

Now Simmons’ is no longer the outsider. After building a colossal audience for his compulsively readable and often very funny columns, the 46-year-old Marlborough, Mass., native has become something of a media mogul.

Shortly after writing a deep-dive into his NBA obsession with the bestselling “Book of Basketball” in 2009, Simmons helped create the celebrated ESPN documentary series “30 for 30” and in 2011 used his rising profile to launch the cultishly adored spinoff site Grantland, which was shuttered just months after Simmons was fired by ESPN in May 2015. The tensions between Simmons and his bosses had been simmering for years, and the relationship grew more contentious with Simmons suspended in 2014 after calling NFL Commissioner Robert Goodell a liar on a podcast and questioning Goodell’s “testicular fortitude” on another, a joke that poked at one of the key revenue sources for ESPN and proved to be the final straw.

“It was business,” ESPN President John Skipper said of the decision at the network upfronts last year, while disputing the idea that the connection to the NFL played a role. In an interview with the New York Times last week, Skipper was more pointed. “I severed our relationship with Bill because of his repeated lack of respect for this company and, more importantly, the people who work here.”

Simmons, who learned of his dismissal on Twitter, has said he regrets the incident for its impact on Grantland but not the sentiment. Last year on his podcast, he said he relished flirting with controversy. “The third rail is sitting right over there,” Simmons told guest Malcolm Gladwell. “You gotta be really careful walking toward it, you don’t want to touch it, but sometimes it’s fun to get really close.”

Network shifts and brash personalities are common in the world of sports programming. Outspoken talk-show host Jim Rome left ESPN in 2012 for CBS Radio and a brief run on Showtime with “Rome.” Keith Olbermann transitioned from host of ESPN’s “SportsCenter” in the ’90s to political punditry on MSNBC and, after a falling out with his bosses, Current TV. Olbermann bounced to FoxSports and back to MSNBC before another stint at ESPN until the end of his contract last year. (Olbermann was also a guest on Simmons’ podcast in March.)

Earlier this month, Simmons launched The Ringer, a sort of Grantland 2.0 that’s partly backed by his new employer, HBO, and includes upward of 25 ex-Grantland writers and editors. One can expect “Any Given Wednesday” to continue working the seam between sports and pop culture, but can Simmons make the move from a talent on the page to the screen?

“With HBO he doesn’t have any restrictions in terms of the properties he can talk about,” says Berke, the sports media consultant. “I think he’s able to speak his mind, and that’s going to be appealing for the audience he’s looking for.”

Of course, he regularly appeared on camera at ESPN before his departure, appearing on the network’s coverage of the NBA Draft as well as “Pardon the Interruption.” Simmons also joined the analysts of ESPN’s “NBA Countdown” for two seasons, a move that led to a mini-controversy when Earvin “Magic” Johnson left the show in 2013 amid some rumblings from network insiders that Simmons had too much power.

Still, his appearances could be awkward, and Simmons has said he’s not trying to compete with the seasoned pros on the late-night comedy landscape, which includes his network sibling Bill Maher and one of Simmons’ former employers, Jimmy Kimmel, who hired him as a writer in 2002 during a brief hiatus from ESPN.

“Those guys are performers, and I’m not,” Simmons told the Hollywood Reporter earlier this month. “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.”

Below, a few suggestions.

Be who you are: The somewhat clumsy, “this-I-believe”-styled early promos for “Any Given Wednesday” offer an impression that Simmons is a brash, no-holds-barred talking head for sports along the lines of Jim Rome. Various controversies aside, he’s not, and while his humor skews toward bro-friendly gags and “Road House” references, his voice is a lot more reasoned.

Profanity is a spice, not a central flavor: We get it: Releasing that first f-bomb in your promo must have felt fantastic after years living under a family-friendly regime. But the more you use it, the more viewers remember how much you couldn’t at ESPN. Now we’re thinking about your old job rather than your new one.

That said, don’t be afraid to stretch: The guests for the first episode of the series include NBA veteran and chat specialist Charles Barkley and fellow Boston partisan Ben Affleck, two personalities drawn directly from Simmons’ wheelhouse. While it’s good to begin from a comfortable place, Simmons has said he hopes to draw guests that include big names from tech and Michelle Obama. Simmons built a career on being a homer, but the further he goes from the familiar the more interesting this show can become.

It’s your show, but not every minute has to be: If there’s anything Grantland’s deep pool of writers proved, it’s your exceptional eye for talent. Now that you don’t have to make sure you’re getting time to have your say (as in one awkward moment on NBA Countdown), you can also give time to some fresh voices.

Follow me @chrisbarton.

‘Any Given Wednesday With Bill Simmons’

Where: HBO

When: 10 p.m. Wednesday

Rating: TV-14 (may be unsuitable for children under the age of 14)