Bill Simmons won’t be your white whale. While today’s ESPN isn’t 1970′s McCann Erickson, The Sports Guy and Mad Men‘s Don Draper would much rather be captains of their own murky fates.
Simmons walking away from his current Skipper isn’t so different from Draper walking out (and driving off) on his new one. Simmons’s September departure and Mad Men‘s May 17th series finale will each mark the end of distinct eras that these iconic (and egocentric) wordsmiths have cultivated and personified.
Like Draper at SCDP, Simmons helped construct a successful empire by creating demand for feelings and insights people didn’t know they couldn’t live without. Regardless of whether you believe happiness is “a moment before you need more happiness” or simply another Boston sports championship, it’s becoming more transparent that both brand builders are really chasing elusive fulfillment. Despite boundless resources at their disposal, fulfillment is surprisingly harder to define and attain.
Although Simmons and Draper are self-made, neither would have reached their creative potential without an audience, infrastructure, and charming, white haired mentorship (John Walsh is Bert Cooper/Roger Sterling).
ESPN and McCann will survive (I’m happy to report the latter has continued to thrive), but solutions can be tricky to visualize after the loss of a true visionary. Especially when they resurface. Only time will tell if standout Grantland staffers including “television analyst” Andy Greenwald embrace cultural shift like Ted Chaough, or pull a Peggy Olsen and take change in stride.
While Don Draper has plenty of experience in burying the past, this is uncharted territory for Clairvoyant Bill. Where will post-Grantland and 30 for 30 life lead him next? Fox Sports, Turner, and Tommy Heinsohn’s seat all sound alluring, but Clairvoyant Bank is calling BS.
After all, “you’re born alone, you die alone and this world just drops a bunch of rules on top of you to make you forget those facts.” But Bill Simmons won’t forget. He’s “living like there’s no tomorrow, because there isn’t one.”
Except the one he’s going to make for himself.
Fans will eagerly hitchhike beside him until he gets there.