On Bill Simmons and Jay Penske

What would Bill Simmons do? Everyone makes this assumption that with Simmons' ESPN contract (nearly) up, he will either (a) take a huge payday to re-up with ESPN; (b) entertain offers from mainstream media competitors like AOL or CBS or Yahoo or Fox; or (c) strike out on his own, as he has intimated and not unlike his buddy Adam Carolla.

I want to go back to something I wrote about a few months ago, because I think that an ultimate option is (d) none of the above.

Instead, watch a recent development in the entertainment and tech news categories: Burgeoning media mogul Jay Penske throwing gobs of cash at successful indie publishers like Nikki Finke and, most recently, Boy Genius Report.

It only makes sense that Penske -- scion of the Penske auto-racing empire -- would want to create his own empire in sports. Penske's Mail Media even owns the ideal sports URL: Fan.com.

And so it would seem to make sense for the LA-based Penske to send an invite to the LA-based Simmons to meet halfway and discuss the kind of deal both seem to want. Penske can offer Bill a few things Simmons would find desirable:

*Tons of money: Penske can afford to pay Bill more than ESPN pays Rick Reilly, commensurate with Bill's status as the most popular sportswriter in the country. Forget the ROI of ad sales; it is reasonable to say that a mere $10 a year iPhone app would more than cover Simmons' annual compensation.

*Equity in his own enterprise: Beyond mere paychecks, Penske can give Simmons a stake in Mail Media -- or an even bigger stake in a spin-off sports property over which Simmons would be given the opportunity to ride the upside.

*Total creative control: It is one thing for Bill to get to write about anything he wants. It is another for Bill to expand on his executive role with "30 for 30" and invest in any project (or talent) he wants. Meanwhile, Penske's team can handle the finances and ad sales.

In this way, it's not unlike Howard Stern's deal with Sirius -- talent not merely as the brand, but as the entire business.

In exchange, Penske gets the biggest individual brand in sports media -- someone who will instantly bring an audience, creative vision and the ability to recruit other talent. Penske's media empire has its biggest star and a platform to be a player in sports media, online or off.

The odds-on result of Simmons' pending free agency is not unlike LeBron's: Rumors of interest elsewhere abound, but ultimately, he will more than likely re-sign with the home team, which has a vested interest (and plenty of resources) to make that happen.

But if Bill is serious about doing something new -- something his -- then no amount of money or responsibility at ESPN (or other mainstream sports media company) will ever totally satisfy him.

And that is an opportunity for Penske -- or any other media-focused investor -- to show Simmons another way.