5. Nick Lachey, former 98 Degrees heartthrob
Pros: Combined record of 222-210 since LaChey's investment. Gave him something to do other than consider what’s left of him after breakup with Jessica Simpson.
Cons: Zero playoff appearances. Oh, and the only thing that folded faster than the "Fame" was LaChey's solo career.
4. Michael Jordan, basketball icon; Nelly, rapper
Pros: Get to hang out with BET owner Bob Johnson … for now.
Cons: Jordan drafted an 11th man (on a good day) in Adam Morrison with the No. 3 pick in 2006 and the hefty Sean May with the 13th pick in 2005. Nelly chose to become a co-owner of a team led by Jordan, who didn't exactly tear it up in Washington, D.C. Team has gone 144-266 in its five years in existence.
3. David Letterman, talk show host
Pros: One Indianapolis 500 championship (Buddy Rice in 2004) and 20 victories in a decade of racing. Gave Danica Patrick her start.
Cons: Going through a rough patch with infidelity admission. Almost missed 2009 racing season because of sponsor troubles.