The union of Bill Simmons—columnist, commentator, on-air personality, and human hot button—and ESPN, the sports media colossus he’s called home for almost 15 years, was no ordinary marriage. It was instead a bizarre, fabled partnership, with triumphs and setbacks and a seemingly endless stream of gossip and drama, both inside ESPN’s corporate campus at Bristol, Connecticut, and on the Internet. It was arguably one of the most important affiliations ESPN had ever entered into with a single individual; Simmons parlayed an online column and rabid fan base into a fiefdom that included the Web site Grantland, the 30 for 30 documentary series, and a starring role as an on-air NBA commentator. And now, it’s over.

Simmons’s contract with ESPN expires later this year. The network’s president, John Skipper, made it official on Friday when he told Richard Sandomir of The New York Times, “I’ve decided that I’m not going to renew his contract. We’ve been talking to Bill, and it was clear that we weren’t going to get to the terms, so we were better off focusing on transition.”

How about that for a shocking finale—not only to Simmons’s employment with ESPN but also to his relationship with Skipper, the man Simmons once considered the best guardian of his interests at the network, if not in the world? When Skipper was head of content for ESPN under then-president George Bodenheimer, he and Simmons forged a bond that was critical in Simmons’s decision to remain at ESPN the last time negotiations were hammered out in 2010. That contract, worth around $5 million per year, made Simmons the highest-paid piece of talent in the network’s history up to that moment.

Later, when Skipper got Bodenheimer’s job and became ESPN president in 2011, the executive dug much deeper into the business side of the company, and deeper into duties other than being Simmons’s protector. Simmons was left largely to fend for himself amongst the ground troops in Bristol, and neither he nor they were pleased with the arrangement. Many in Bristol believed Simmons, who ran his mini-empire a continent away in Los Angeles, had a heightened sense of entitlement, and operated as if certain rules simply did not apply to him. They resented the fact that he sought, and sometimes got, larger roles in decision making and policy making than talent typically did.

Problems and tensions were clear to many throughout 2014. Then all hell broke loose in the fall when, at the height of the Ray Rice domestic-abuse scandal, Simmons called N.F.L. commissioner Roger Goodell a liar during a segment on his podcast. ESPN suspended him.

The suspension was supposed to include a two-week dock in pay, but when he looked at his paychecks afterward, Simmons could hardly help noticing that the checks were for the usual amount. He interpreted this as ESPN holding out an olive branch; the public censure had been just for show, Simmons thought, there was no financial penalty after all.

That might have smoothed things out between Simmons and management—but on December 19, Simmons opened his pay envelope and was not pleased. Two weeks’ worth of salary wasn’t there: “Merry Christmas, Mr. Simmons—here’s your lump of coal.” Simmons had had enough. The chances of him staying at ESPN from that point onward became less and less probable.

Even so, Simmons was curious to see what would happen when ESPN started seriously talking about a new deal. There was one broad conversation. Simmons made a point of not putting forth any specific requests—a pre-emptive strike against ESPN later trying to say, “We were unwilling to meet his demands so we didn’t renew him.” But no dollar amounts were specified, and no actual back-and-forth negotiations went on.