Simmons2 - Joe Murphy:NBAE, via Getty Images

The DeSimmons

You know that feeling when you’re in Vegas with your buddies and you start losing and you start losing fast?

Something like… you’re playing blackjack… you’ve built a big lead… but then you keep hitting on 12 (like you always do) and you don’t stop busting.

And then the cash you were going to spend on your daughter’s birthday party also ends up down in one of Steve Wynn’s alimony accounts, and all of a sudden your cashed-up buddies are going mental over at the wet-t-shirt hot-dog-eating contest and you’re stressing for the rest of the weekend about how you’re gonna be able to make a Frozen birthday cake from old kitchen scraps.

You know that feeling?

No – neither do I.

But Bill Simmons might.

And that might be just how the Number One Seed in American Sports-ish-Pop-Culture-ish Writing is feeling right about now.

If, like us, you enjoy over-educated sneaker-wearers riffing about sports played particularly well by tall Americans, you’ve probably heard of Bill Simmons.

And you’re probably aware of the former Grantland boss’s employment pickle, as at June 2015.

After being boned by ESPN, Simmons can’t write or publish for anyone until his $5 million contract expires some time in September.

But then he hits free agency! And that’s when, for us sports watchers and sports-watcher-watchers, things could get really interesting.

What’s Simmons going to do? Where’s the sharpest brand in US sports media going to take his talents?

Well, in the spirit of Simmons himself, let’s try to break down his employment options. And let’s break them down in Simmonsonian terms – by ad nauseam references to his legacy.

The way I see it, there are four places Simmons could land. And they all have very different implications for the Simmons Legacy.


Option One: Move to a different TV/Media network.

The safest option, obviously, but also the one with the lowest legacy ceiling. Sure, Simmons could join the TNT crew and write for Bleacher Report, probably for millions of dollars a year. And Mark Wahlberg could’ve stayed with Donnie in NKOTB, probably for millions of dollars as well.


Option Two: Go it alone.

But Marky Mark broke with Donnie, got his own funky bunch, maintained a disciplined abdominal regimen, and elevated himself into another of America’s most recognisable Bostonians.

If Simmons were to follow the Wahlberg model, there’s obviously a much greater legacy upside in play.

And the business strategy pretty much writes itself… find a Silicon Valley nerd with a hankering for pop culture relevance… extract a check for $100 million… take an ownership stake in the company you co-found … get Jalen and Jacoby over… hire some underpaid kids from Slate… you’ve got Grantland Redux!


Option 3: Join Google.

But there’s a good chance that the Silicon Valley Nerd’s cash will run out.

And media – well – media doesn’t seem to make any money any more, so maybe you don’t want to take an ownership stake in a new venture.

So if you’re Simmons, why not team up with a business that does make money?

Why not lead the sporting arm of a monopoly internet goliath?!?

Imagine the day when Google says, fuck it, we’re going to outbid every dinosaur outlet going and buy the online sporting rights for the NBA, MLB, AFL, NRL, whatever. Surely that’s on the cards.

And Brand Simmons could be a part of this. Simmons could lead Google’s coverage into every broadbanding home on the planet.

In legacy terms, this would be the Jordanian.


Option 4: Become the Sports Tsar.

But it might not be the GOAT move.

Regular Simmons readers will know that one of his regular tropes is to appeal to Obama to appoint him Sports Tsar – in which he would be the ultimate decision maker for sporting organisations needing a dose of common sense.

Well… Simmons is unemployed… Obama is a lame duck… this is not beyond the realm of possibility.

And let’s face it. Simmons could be good at the job.

He obviously likes organising things.

He’s never seen a basketball player that he hasn’t felt the need to categorise (“poor man’s Bird” “rich man’s McHale”) or slot into some sort of list (“top ten guy” “pantheon player”).

These are the obvious character traits of an arch-bureaucrat.

So do it, Bill. Call Barry. Forget ESPN, become the ES-PM.




Jake Saulwick is a Lebronologist and City Editor, The Sydney Morning Herald. He is a contributor at New Albion.