Richard Hatch: First winner, nudist, gay, got arrested afterwards for tax evasion.
Sue Hawk: Was in two seasons with Hatch (1 & 7), and after an incident involving Hatch, she got triggered hard.
Michael Skupin: Fell into a fire pit, forcing him to quit.
He came back for a later season, but was recently arrested for CP
http://people.com/crime/survivors-michael-skupin-sentenced-child-pornography/
Colby Donaldson: 2nd place in 2nd season, became more popular than the winner.
"Boston" Rob Mariano: Finally won after 4 times on the show, proposed to his now-wife after the second time through. Went on to be in "The Amazing Race" twice, lost both times.
Jon Dalton: The ultimate

, fooled everyone into thinking his mom was dead for sympathy. It didn't win him the money, though.
Rupert Boneham: Literal pirate, known Libertarian.
Sandra Diaz-Twine: Won both times she was previously on, hoping to make it a third time in this current season.
Jessica "Sugar" Kiper: Two-time loser, had her bra ripped off during the first day, played a character in L.A. Noire
Russell Hantz: Got to the finals twice, never won, tard raged about it. Got voted out second in a third attempt. Had a failed TV show called "Flipped Off." Arrested in 2010
Jud "Fabio" Birza: The little asspie that could. (Sorry for the shit quality)
Phillip Sheppard: I got nothing. He's quite literally an old skitzocow.
Will edit with more notable players.