Many options may be the best option for Bill Simmons

Bill Simmons
Brian To | FilmMagic | Getty Images

Now that marquee sports columnist Bill Simmons has been let loose from his ESPN contract, Vice Media wants in.

But heading exclusively to a single media organization, even one that has received as much recent buzz as Vice, might not be Simmons' best or only choice.

David Katz, founder of sports culture portal who has known Simmons for more than a decade, said, he could see Simmons signing with Vice or with a major sports network like Fox Sports. But thanks to the ubiquity of digital media, Katz said there's no need for the sports columnist to tether himself to one organization.

Read More

"We're at a time in the media landscape where Bill, who is a personality and celebrity in the media world, has an opportunity to flip the mode and go direct to consumers," said Katz, former head of Yahoo Sports.

On Friday, Vice CEO Shane Smith tweeted at the sports columnist to join the millennial-leaning media publication.


Vice declined to comment, and representatives for Simmons did not respond to requests for comment. Last week, ESPN President John Skipper said the network would not be renewing its deal with Simmons, who was reportedly paid $5 million a year.

On the surface, a deal with Vice might be a win for both parties. The media company is looking to build a larger presence, fueled by a $500 million financing round from A&E Networks, and Technology Crossover Ventures last August that gave the company a valuation of more than $2.5 billion. Adding a household name like Simmons to the Vice Sports roster would offer more incentive to advertisers and investors to come on board.

In turn, Vice could offer Simmons some things he desires, including a TV presence through a rumored A&E deal that would rebrand the network's H2 channel into a Vice property this fall. What's more, Vice has a deal with Time Warner's HBO to do a weekly news show. Time Warner also owns Turner Broadcasting, whose TBS network broadcasts NBA games. Simmons has a special interest in the NBA.

At Vice, Simmons would also be able to expand his global presence, as well as find a home at a company that embraces contrarian voices—something he's notoriously had run-ins with ESPN about in the past.

Read More Bundle? You can't stop technology: Ex-ESPN head

However, Katz believes what makes more sense for Simmons is to go for a hybrid approach. The sports personality could launch his own digital venture—similar to what former Washington Post and New York Times reporter Sharon Waxman did when she launched entertainment news site The Wrap—while signing partnerships with bigger networks and media conglomerates for certain projects.

It's a sentiment echoed by Re/code senior editor Peter Kafka on Twitter, who explained he sees Simmons signing a TV deal and starting his own venture online. He added that going to a smaller media conglomerate like Vice "makes no sense."

"These deals will look very similar to a top athlete's free agency deal in certain sports, which can cost tens of millions of dollars," Katz said. "He's going to get a deal similar to the athletes that he covers on a daily basis."

Disclosure: NBC News group is a minority stakeholder in Re/code and has a content sharing partnership with it.