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4. Sol Campbell - Tottenham Hotspur to Arsenal, 2001 (free transfer)
2001 was not a good time for Tottenham Hotspur fans - then club captain Sol Campbell declined to renew his contract with the club, and chose instead to move away. His departure was not the topic of discussion, however, but rather the team he chose to go for. Campbell made the move from Spurs to their biggest rivals as he travelled across North London to join Arsenal Football Club, who were starting to achieve great things under Arsene Wenger.
The defender's reasoning was simple - he wanted to win trophies, and he did not think that Spurs were in a position to do that. As such, a move to Arsenal made the most sense. However, football is not as black and white to fans as it is to a few players. The former Spurs' captain move was met with horror from the Spurs faithful, and he was at the end of some homophobic and racial chants which are never warranted.
Campbell was part of the famous Arsenal Invincibles' squad, so his ambition was ultimately met. However, that does not change the fact that his decision is one of the most treacherous acts we have seen this century.
