FanHouse's Michael David Smith lays odds on who might succeed Will Leitch at Deadspin. Many of the usual suspects are mentioned (Daulerio, KSK guys, MJD), some long shots (Brooks, Nik Richie, Sarah Schorno), and a handful of guys who would probably cause the Deadspin readership to revolt (Shanoff, Simmons).
If I'm running it I probably give it to Daulerio who, despite his reputation for outlandishness, is a solid writer who seems to care about sports more than he cares about becoming some larger than life character. I fear that most of the rest of those candidates -- particularly the KSK guys -- would be fairly disastrous in that a little of what they do best (audaciousness; shock; creative profanity) goes a long way. I get a nice laugh out of their stuff when taken in small doses, but I fear the site would become a parody of itself if someone gave them 20 posts a day.