Gerrard’s story is one of the most tragic on this list because he was a brilliant servant for Liverpool. He came through the club’s youth ranks before captaining the team to glory. However, he never won the Premier League title with his boyhood team and arguably cost his team a long-awaited victory (via The Mirror).
The notorious career-defining moment came against Chelsea in 2014. Liverpool was ahead of Manchester City with a game in hand. Mamadou Sakho sent a weak backpass to Gerrard but the captain slipped as he attempted to retrieve it. Then Chelsea’s Demba Ba stole the ball and scored the goal that snatched Gerrard’s dream away.