How Many Times Has Boston Rob Won ‘Survivor’?

Rob’s won Survivor once, but he’s been on the show a total of six times. The veteran’s first time was on Survivor: Marquesas, where Rob, assigned to the Maraamu tribe, was eventually seen as the biggest target by the Rotu tribe. He lost that season. His second time was on Survivor: All Stars, which was two years later. He got to reunite with other players, including now-wife, Amber. He lost 4-3, but won when he proposed to Amber. Rob came back for Survivor: Heroes vs. Villains, where he was assigned to the Villains tribe and was their leader.  He last that season, too.

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