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A year after his nasty split with ESPN, Bill Simmons, the Boston Sports Guy, is back with a big new HBO show — and a few scores to settle.
A year after his nasty split with ESPN, Bill Simmons, the Boston Sports Guy, is back with a big new HBO show — and a few scores to settle. bret hartman for the boston globe/For The Boston Glo

New England sports fans first came to know Bill Simmons in the late ’90s as The Boston Sports Guy. The twentysomething Holy Cross graduate was one of us, a fan — but a fan whose writing for AOL’s Digital City Boston just happened to crackle with passion and laugh-out-loud one-liners before we even knew what LOL meant. Naturally, Simmons did not remain our secret for long. ESPN snapped him up, he dropped “Boston” from his Sports Guy moniker, and he soon became a sensation with such columns as “Is Clemens the Antichrist?” Simmons didn’t just ride the wave of sports writing in the Internet age, he helped shape it while succeeding wildly in various forms of old and new media.

Since moving to Los Angeles in 2002 to write for Jimmy Kimmel’s then-fledgling late-night program, Simmons has penned two best-selling books, launched podcasts that have blossomed into a network, analyzed the NBA on ESPN, brainstormed the idea for the acclaimed 30 for 30 film series, and developed the popular long-form website Grantland. And then came that ugly split with ESPN. After Simmons called NFL Commissioner Roger Goodell a liar on his podcast, the network brass suspended him and then essentially notified Simmons he was fired in the pages of The New York Times.


Now 46, Simmons has just launched a new sports and culture website, The Ringer, and is taking on perhaps his boldest initiative yet: becoming a talk-show host. His half-hour interview program Any Given Wednesday premieres June 22 at 10 p.m. on HBO. I caught up with Simmons by phone to discuss his plans for the show, his acrimonious departure from ESPN, and how he stays connected to his hometown.

This is a remarkable progression from how we first knew you — the wise guy you wished was sitting on the next bar stool over during the big game — to a host of his own show on a prestigious cable network. Why is the time right for you to do this?


I’ve been writing my column since college, day in, day out, or week in, week out, since 1997. The Internet really changed over that time. By the early part of this decade, there was just so much content online that no matter how well you wrote something, people would read it, they’d like it, and they’d move on to the next thing. That’s what people do on the Internet. That’s fine, that’s great. I still love the Internet, but I think the impact of a TV show still matters. And, honestly, I just really wanted to do a TV show.

So my thought was if you can do a show like this correctly, the show I want to do, with people that are basically like the Harvard of TV [his writing and production team includes alumni of The Daily Show], that was basically the highest impact I could have. I’ve taken the column in pretty much every direction I could ever go with it. This seemed like natural evolution.

RELATED: Simmons bashes ESPN in first new podcast

What is the format of Any Given Wednesday? Why did you structure it the way you did?


There will be two big conversations during the show, and one will be geared around some sort of topic. The goal would be to have one more-topical conversation with two other people that kind of makes sense why all three people are talking about it. And then a big interview, because as I’ve learned from my nine years of doing my podcast, I love interviewing people.

Your podcasts have always sounded like conversations between good friends.  How do you translate that camaraderie to TV?

The pop-culture side [will be easier]. The athlete side is a little hairier. As you know, some athletes just aren’t good interviews.

The majority, I’d say.

And it doesn’t make sense to have a bad interview, right? So that’s one we’ve put a lot of thought into from that standpoint. One of the ways to do it is to put people in pairs. Like Tom Brady by himself, I just don’t think he says anything. He’s in the prevent defense the whole time, you know? But if he’s with [Julian] Edelman, or if he’s with [Wes] Welker, or if he’s with [Randy] Moss, just somebody that almost becomes the personality and Brady plays off that and that guy can pull some stuff out of it, now that becomes fun.

I’d love to have Tom Brady, but if it’s just me and him, why is that any different than what I’ve seen on SportsCenter or Sunday Conversation? How do I make that fun? Do I put him with Ben Affleck? How can I bring that out? The only reason I’m talking about Brady is that he’s not going to do my show — he’s not going to do anything. I think this lawsuit is going to keep going forever.


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You have longtime friends as regular podcast guests. Your dad is a regular. And your staff at Grantland raved about the inclusive atmosphere. I assume this is deliberate. How will you bring that to your new projects?

It was one of my biggest lessons from [the ESPN-owned projects] Grantland and 30 for 30. I think people are as good as the people around them. We had such a cool thing at Grantland that I think we’ll be able to replicate at The Ringer with everything we’re doing. A lot of it was about the culture. It’s really hard to explain, but if you get enough people in a good situation, there’s a little bit of a selflessness that comes out. They start behaving a little differently. They don’t care about credit as much. People realize they’re on a winning team, and this is great, and I just want to help the team. It’s really not any different than what happens on a sports team.

Let’s talk about what happened to bring you to this place. ESPN president John Skipper dropped the bombshell in May 2015 that your contract would not be renewed — essentially publicly firing you — by giving word of your status to a New York Times reporter before informing you. Did you have a sense that your time was ending there before ESPN took matters into its own hands?


I knew I was probably going to leave when they took money out of my paycheck [for the suspension] six days before Christmas. I never thought they were going to take the money out, but they did, and from that point on, I knew I was out. The only thing, the only reason it wasn’t 100 percent is because of the way I felt about people at Grantland. I just couldn’t imagine leaving. I hired every single person that worked there. I think people are going to look back at the staff we assembled and be like, they had all of those guys in one place? I almost felt like [Bill] Parcells leaving [after the ’96 Patriots lost the Super Bowl]. Let’s face it, the ’97 Patriots were going to be his best team.

“If [ESPN] wanted to keep Grantland, they would have. They’ve kind of designed the company where everyone is replaceable. It’s very Belichickian,” says Bill Simmons.
“If [ESPN] wanted to keep Grantland, they would have. They’ve kind of designed the company where everyone is replaceable. It’s very Belichickian,” says Bill Simmons. bret hartman for the boston globe

When did you figure out where you were going? It was an irresistible parlor game for media types and sports fans to speculate where you’d end up.

It became clear pretty early that HBO was the right place. I actually met with them in March [2015]. I left the meeting, and it was like my head was clear for the first time in two months. It was the first time I realized: “Oh, this is really going to work out. Whatever happens, this is going to be awesome.’’ I just felt in my bones I was probably going to work for them or Showtime.

Seriously, it was the greatest thing [ESPN] ever did for me. It was funny, when it happened — and they tried to embarrass me, it is what it is, they lied to me and they lied about me — people in the outside world were like, “Oh, no, what are you going to do?” And I was like, “What do you mean? This is great! They just paid me not to work for five months. [Simmons left shortly after the Times story broke.] I’m going to figure out my next step. This is awesome.”

The worst thing they could have done was make me work for five months knowing I was leaving. It gave me time to figure everything out, figure out a real game plan. I took it personally. In a lot of ways, it was a great thing that it played out like it did, because it lit a fire under my ass.

RELATED: ESPN cutting ties with Mass. native Bill Simmons

Were there any other offers that you seriously considered? Were there any surprises during the process?

The thing that surprised me is that I thought Showtime was really going to get involved. And I think the football thing scared them off — I know it did, there’s no question. That became a football decision for them. Football is their biggest partner; they basically told me that [Showtime declined to comment]. If I learned anything over these last two years, it’s that the NFL is a powerful entity. It really is. NBC [a major NFL television partner] never even made a phone call to me. There’s a gigantic list of people that reached out. I never heard from NBC. Not an e-mail, anything.

Was your criticism of the NFL the main reason ESPN decided to move on from you?

I think that was part of it. It was definitely the biggest reason for things ending how they did. They don’t mess around, the NFL. I look back at the ESPN thing and I’m kind of amazed I made it 14 years. Think about it this way: Could [Charles] Barkley have made it 14 years at ESPN? He certainly couldn’t have been as outspoken. Who could have made it that long? The over-under for me should have been like seven [years].

Would you invite John Skipper and Roger Goodell on Any Given Wednesday? It does seem like they’d be guests with something in common.

[Pause.] I would love to have Goodell.

You know he’d never do it.

He’d never do it. And he’d go into it in that weird mode where he’s just spouting cliches and you don’t know what he’s saying — he’s incoherent. I think it would be fun to interview him. It would be like riding a bull, and you’re just trying to hold on to the saddle wondering what the hell is going on.

And Skipper? You guys were close once, or at least that was the common narrative.

I don’t think Skipper is going to be on. With the way last year has gone, with it being way more acrimonious than I think it should have been, what they did to Grantland at the end and what they tried to do publicly to the people that left — make it seem like it was their fault — that pushed it to another level. Those are good people. If they wanted to keep Grantland, they would have. They’ve kind of designed the company where everyone is replaceable. It’s very Belichickian. They’re designed to keep rolling no matter who is working for them.

You’ve been in Los Angeles since 2002. Your work is there. You’re raising a family there. How do you maintain the ties to Boston, especially the sports teams?

I still watch the games. I don’t watch nearly as much as I used to. From a Red Sox standpoint, I still watch sections of games now. I kind of can’t believe that there was a time in my life where I watched every Red Sox game. That era was actually within the last 20 years. I feel like I watched 93 percent of the 1999 season. But baseball is just so freaking long. The DVR helps, especially with the Celtics.

Is there anything about the Boston sports scene that you don’t miss?

I definitely don’t miss the media stuff. I’ll read about sports radio and the stuff you write about, and I’m like, “Oh, my God, I’m so glad I don’t live there. I’m so glad.’’ This stuff was terrible 20 years ago. The biggest fault with Boston sports is that the media makes it less fun intentionally. They know Boston people are crazy, they know ways to get people fired up, riled up, and upset and angry.

If you can do that well, it can be a lucrative career.

They know how to push buttons. That’s the success story of just about everyone the last 20 years in Boston who popped up. The people you and I grew up with, people like Ray Fitzgerald and Leigh Montville and Bob Ryan, they didn’t have to do that. I was never able to reconcile where it went. It does resonate with some people, I guess. If one of the drive-time hosts says, “If Brady doesn’t win his fifth Super Bowl, he’s overrated,’’ people go [expletive] crazy. That’s the one thing from 3,000 miles I don’t miss.

That lost angst is like a ghost limb for some fans, isn’t it? Boston’s pro teams have won nine championships since 2001, and yet there are those who long for the days when championships weren’t being won.

Oh, yeah. Success really has had an interesting impact on all of this stuff. Part of our DNA is just assuming something would go wrong and yet still believing that it wouldn’t. That’s like the Boston fan in a nutshell from the first 30 years of my life. “Wouldn’t it be great.’’ “This is the year.’’ And then it all goes to hell and it’s “I knew it.” The DNA is still in there, but it’s really hard to justify. You should hear the conversations I have with fans from other cities. They’re so mad at Boston. They don’t think we should be allowed to complain about anything for like 20 years.

Are you nostalgic for your time in Boston? Do you even have time to be nostalgic, to take a step back and say, man, what a journey?

I think about that all the time. I’ve been really lucky. Twenty years ago, I literally had no income. I was trying to freelance, and it literally was a disaster. I wrote like one thing for the Worcester Phoenix in two months. And I was like, yeah, I’m going to freelance. I basically just bartended and was a waiter for a good solid year before I launched my site.

People know my story, but it’s hard not to think about it. I always thought something good would happen, but I never really knew it. You give up hope a lot of times, or you begin to doubt that it will happen, or you get down. I know there are a lot of people out there that probably feel that way. I think about that all the time. It would be weird not to. I’ve been really, really, really lucky with some of this stuff. And some of it also happened because I worked my ass off. If you work hard, you have a better chance. I’m really happy. I’m grateful. And I’m going to keep working my ass off.


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