20. Raheem Sterling
Liverpool signed Sterling as an exciting teenager and developed him into an electric forward. It appeared as though he was the future of the team but he rocked them when he demanded to leave. This infuriated Liverpool who poured millions into his development but they didn’t stand in his way.
Sterling didn’t believe that Liverpool was in a position to compete for the top prizes. He also knew that Manchester City would pay him more money so it made sense. City signed him for almost $50 million and Sterling won many honors with the oil-rich franchise (via Bleacher Report).