6) Jermaine Pennant
When the winger signed for Arsenal, much was expected of him. However, many loan deals, arrests and even once claiming to be Ashley Cole when caught driving on the wrong side of the road, meant that he never had a chance at the Gunners.
He did manage to turn it around for a while, earning a move to Liverpool via Birmingham City. Then his attitude hit again, rarely training while at Real Zaragoza before coming back to England with Stoke City. It didn’t last long there either, and is now playing in the Indian Premier League.