'90s Team(s): Seattle Supersonics (1990-99)
Before being replaced (after one season) by Kevin McHale, the newly enshrined Hall of Famer was an analyst for NBA TV and occasionally NBA on TNT. He was also featured on the very short-lived, Onion Sportsdome on Comedy Central. Payton has been very clear that he does not want his number retired by the Oklahoma City Thunder as a show of solidarity to the city of Seattle. He has stated that he wants to bring back a team to the Emerald City.
Between working with charities, writing a book and working with Nike on a re-launch of his shoe, he's also been mentoring John Wall. If you ever have an extra couple grand lying around you can get your ass kicked by him in a game of one-on-one. Or, if you prefer, sit in awkward silence (knowing that you paid the man to eat dinner with you) as you two share a meal.