Bill Simmons returns to ESPN Wednesday after the network suspended him for three weeks after he called NFL Commissioner Roger Goodell a "liar" and dared ESPN to punish him during a podcast.

This is not the first time Simmons, one of the most popular sports personalities in the country, and ESPN have been at odds. Over the summer, Simmons abruptly left ESPN's basketball pregame show, "NBA Countdown" after a tumultuous and brief tenure.

ESPN banned Simmons from Twitter for three days last year after he criticized a segment on the ESPN2 program "First Take." Simmons called it "awful and embarrassing for everyone involved."

His most recent punishment sparked an online movement supporting Simmons and criticizing ESPN for over-censorship. The online movement included the trending Twitter hashtag "#FreeSimmons."

With a string of disagreements between the two parties, it's fair to wonder whether Simmons will look elsewhere once his contract expires next year. An even more interesting question to entertain is if Simmons would be able to prosper without the safety net of ESPN.com's 80 million monthly visitors and the network's considerably far reach.

"His [Simmons] return marks only the beginning of the intrigue, as he and ESPN jockey in advance of the expiration of his contract next fall," wrote Jonathan Mahler and Richard Sandomir of the New York Times. "The implications may be far-reaching, as Simmons could become something of a litmus test for the rising power of individual brands in a rapidly shifting media landscape.

A potential stand-off between Simmons and ESPN could help answer the chicken-and-the-egg question for current mainstream media. Is it the popular personalities that further the success of large media companies or is it the wealth of resources and platforms that those companies provide that establish the media members?

"The way I look at things is what is the community around Bill Simmons and how big is that community?" said Betsy Morgan, a president and the chief strategy officer of Glen Beck's TV network and website. "If Bill didn't live on ESPN, would that community still have a way to find him?"

Some in the industry seem to think that the clicks, eyeballs, downloads and attention would follow Simmons wherever he goes, even if her were to set up something of his own like Beck.

"He's a huge brand and sports are a passion point," said Gary Vaynerchuk, an Internet entrepreneur who invests in media companies. "Right this minute there is so much money being thrown around he could probably raise a disproportionate valuation for Bill Simmons Inc."

Others are not so optimistic.

"Knowing what I know now, I think he should say: 'I had a breakdown, I didn't mean what I said. I'm back at ESPN and I love it,'" Kenneth Lerer, co-founder of the Huffington Post and chairman of BuzzFeed, said. Lerer doesn't believe starting something all your own and succeeding, even as a popular sports personality, is an easily accomplishable goal.

What separates Simmons from your average sports personality is the versatility and creativity he brings to the table. He made his name as a columnist who weaved in personal loyalties and entertaining pop-culture references as often as possible. He took full advantage of the internet's offerings by galvanizing a large and committed following on Twitter (almost three million followers). His weekly podcast "The B.S. Report" is routinely one of the most downloaded items on iTunes. He was also instrumental in creating ESPN's award winning "30 for 30" documentary series and Grantland.com, a popular destination for sports and entertainment happenings.

"99 out of 100 sportswriters have no entrepreneurial leanings," said Michael Wilbon, a co-host of "Pardon the Interruption" on ESPN. "Could Bill be the exception? I guess. I'm not ruling out the possibility."

Simmons still has a year to go on his contract, "plenty of time for cooler heads to prevail," Mahler and Sandomir wrote. But to guarantee Simmons, who "insiders say earns more than $5 million a yar," will stay with the World Wide Leader in Sports would be foolish. The New York Times duo poignantly ends their article by reminding us that Bill Simmons is a guy who is not averse to risk.

"I am not afraid to fail," Simmons told the Huffington Post in the past. "And beyond that, I am not afraid to fail violently and miserably. So anything is possible."