5. Tony Vlachos
Second season: Game Changers
Okay I know what you’re all thinking here – How can Tony be included here if he was the second boot in his second season? I hear you, I really do, but hear me out with this one.
Tony went into Game Changers as one of the sneakiest winners in the history of the show. He played REALLY aggressive from the jump in Game Changers and it cost him. Sandra went after him, took him out, and he was the second person booted from the season.
So, how did that benefit him then? Well, because without that poor showing in Game Changers, Tony goes into Winners at War as arguably the biggest threat for what he was able to do in Cagayan. Seeing him get booted so early in Game Changers made others see that he wasn’t the huge threat he was in that season and they didn’t have to take him out anytime soon.
And guess what? It worked! Tony went on to get zero votes thrown his way in Winners at War and became the show’s second only two-time winner. I’d say his second chance worked out well in the long run.
4. Jeremy Collins
Second season: Cambodia
I mentioned that everyone who won on their second season was a lock to make this list, so obviously Jeremy is going to make it on here because of that. He was a fan favorite on his original season of San Juan Del Sur and was blindsided that season because he was a huge threat.
Jeremy was voted onto Cambodia by the fans and he came up with the meat shield strategy, which was implemented again in Winners at War. The meat shield strategy essentially means that the strong players keep each other around as protection. This strategy by Jeremy helped get him to the end in Cambodia and his idol play at the final six kept him around so that he could make it to the end.
Jeremy is obviously someone who benefitted on his second go of it because not only did he win the season, but he won in a unanimous vote. He even potentially played the show’s third ever perfect game (debatable though because he did have three votes sent his way that were negated by an idol play). He is considered to be one of the best winners in the history of the show, so his second chance was huge.