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After all, Simmons’ dad had worked in the same Boston-area school system for 33 years, and he didn’t understand why his son’s tenure at the sports-media behemoth needed to end after just 14. “My dad’s a huge loyalty guy,” says Simmons, whose then-boss, ESPN chief John Skipper, announced the Bristol, Conn.-based company would be severing ties with the known firebrand via an interview with The New York Times. Simmons had received no heads-up, instead seeing Skipper’s comments about his fate for the first time in his Twitter feed in the early hours of May 8.
“My dad was just like, ‘What the f—? Are you telling me everything?’” says Simmons, seated a year later in his multi-room office on the Sunset Gower Studios lot in Hollywood for a THR cover story. “I’m like, ‘Dad, this just got really f—ed up.’ I couldn’t even point to one thing. It was a lot of little things.”
Among the elder Simmons’ concerns: what his son, a sportswriter turned multimedia juggernaut, would do next. And to that end, would it ever be able to match what ESPN had offered. But calming his father’s nerves would prove easier than Simmons had anticipated. Within days of being ousted — Simmons declines to use the term “fired” as he continued collecting a paycheck until his contract expired in September: “Part of me thought about leaving early and I was like, ‘No, I’m actually gonna take every dollar they owe me’” — the list of suitors had already grown lengthy.
Simmons sent his dad a Word document of all of the outlets, including Turner, Fox Sports and Hulu, that had reached out following the Times story. “My dad was like, ‘Oh, so this is gonna be okay,’” he says, the memory drawing a smile to his face. “And I told him, ‘Yeah, it’s gonna be just fine.’”
By late July, Simmons’ next act became official. He signed an exclusive, multiyear deal with HBO, which sources say is paying him between $7 million and $9 million per year. In doing so, he had agreed to create a weekly talk show, which will launch Wednesday at 10 p.m., as well as to produce or consult on other sports-themed programming for the network and its digital offshoot, HBO Now. As part of the pact, Simmons won’t be able to do video or TV work elsewhere, a stipulation that fellow network personality Shane Smith famously did not have in his contract. (Smith has since inked deals for several non-HBO TV projects, including a stand-alone Vice channel in partnership with A+E Networks.)
“The Shane thing was probably not great for me,” says Simmons. “I think it affected how they approached what to do with me because Shane had this HBO show that helped blow up his whole financial model in a really good way and then [HBO] didn’t profit in it. That was illuminating for them — that if we’re giving somebody this platform, they can’t just then go and do 19 other things.” He pauses, and then adds: “And that’s the way they should think.”
Before Simmons signed with HBO, however, he and his agent, James Dixon, took calls, meals and meetings with a host of other potential suitors. “I talked to everybody,” Simmons says. “The truth is there’s just not a lot of content people out there and everyone wants content.”
Among them: a sit-down with Showtime president David Nevins and his boss, CBS Corp. CEO Leslie Moonves. Simmons had known and respected Nevins for some time, and had even discussed potentially working together when he was still at ESPN. Once it became clear Simmons’ run at the sports network was over, he took a formal meeting at the CBS offices in Los Angeles. “Moonves started out the meeting by telling me how they probably couldn’t hire me because the NFL is his No. 1 partner,” says Simmons. “He was like, ‘The part I can’t figure out here is how you’re gonna work for us and what if you go after the NFL.’ I’m like, ‘I can’t figure that out either, but I can tell you it’s not that appealing of a situation if I have to worry about it.’”
He continues: “We talked for, like, an hour and as we talked, I could see him talking himself into me … and we left it in a really good place.” The host recalls walking out of the meeting feeling as though it had gone very well, a characterization he says Nevins confirmed. “And then two weeks passed and then [David] called all bummed out. He was like, ‘We can’t.’ The NFL was a real factor for me, and I never anticipated that.”
His courtship with Yahoo played out quite differently. As Simmons recalls, CEO Marissa Mayer contacted him through “seven or eight different people” before reaching him directly. “Somehow she got my number and within five days we were having dinner in Beverly Hills,” he says, revealing the struggling web portal was interested in him running Yahoo Sports and doing Katie Couric-style interviews. Simmons adds, “I thought it was a real possibility, so I did some research. I didn’t know what was going on with Yahoo, and I’m reading the stories, and I’m like, ‘Ooh, this is bad.’”
Fox Sports, another potential option, would have reunited Simmons with former ESPN executive and pal Jamie Horowitz, but he jokes that he was too competitive to sign on at a sports channel still very much in the shadow of ESPN. According to Simmons’ agent, there also were several Silicon Valley suitors eager to get into the Simmons business, be it through producing his next project or simply investing in whatever he did next. Among them, per Dixon: Google, Twitter and Snapchat.
As for the other, more traditional Hollywood outlets, Simmons acknowledges he thought Netflix would be more aggressive, given its $5 billion content budget and seemingly insatiable appetite for programming. What he found instead is that they were more interested in him for his documentary expertise, which he had gained from ESPN’s 30 for 30, than they were in a Simmons-fronted show. The streamer that seemed to really surprise and impress Simmons was Hulu. “After I signed with HBO, they were the only people I emailed just because I really liked them,” he says. “I was like, ‘You guys are f—in’ awesome, so you know.” Just not, apparently, as “f—in’ awesome” as HBO.
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