To me, Bill's biggest fault has always been his intellectual laziness. He was revolutionary when he was young - I'm a few months older than he is - but he never refined the gimmick. He needed to grow in new directions, but he never bothered.
I really enjoyed his early work. He was doing stuff no one else had the freedom to do - and there are a ton of other sportswriters of our age who envied him for that. But now everyone has podcasts and amusing Twitter accounts. What sets him apart?
He's not a great analyst - his giant basketball book is awful once you look past the pop-culture references - and the frat-boy white dude gimmick went out of style with George W. Bush.
In this day and age, he's a valuable role player. Deadspin 2.0 should hire him, give him a podcast and a place to drop his running diaries and his mailbags. Don't let him make editorial decisions, don't let him make hiring decisions and tell him to drop the casual racism and sexism.
He can be successful in that role. You just can't build a team around him.