Ranking the 50 worst Premier League transfers of all time.

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Having looked over 28 years of transfer data for my list of the 100 best Premier League transfers 100-51 here and 50-1 here it is time to go in the opposite direction. Say goodbye to Thierry Henry and hello to Bebe. It's time for the 50 worst transfers in Premier League history. One more note: All the transfer values in this column are from Transfermarkt. Some of that data might be at odds with what was publicly reported at the time.

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10. Didier Drogba, ST, Chelsea

Signed from Marseille for £34.7 million, 2004
Drogba was a bit of a late bloomer, as the Ivorian was really still a middling striker in Ligue 1 until 2002-03, when he scored 17 goals for Guingamp and followed it by adding 19 in 35 appearances for Marseille. Drogba was 26 when Chelsea signed him in July 2004, which is older than it might seem for world-class strikers. Fernando Torres, for one, was 26 when Chelsea signed him away from Liverpool, only for the club to find Torres was already on the downswing of his career.

 

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9. Roy Keane, CM, Manchester United

Signed from Nottingham Forest for £7.7 million, 1993
Uncompromising is the first word that comes to mind when I think of Keane, which famously manifested itself in both valuable and destructive ways. Most midfielders wouldn't take to the in-house television network to bash the club's younger players. Most wouldn't leave their national team on the eve of the World Cup because the facilities weren't up to standard. Most wouldn't take a shot at their own home supporters and call them the "prawn sandwich brigade." Just about nobody would wait three years to try to injure Alf-Inge Haaland.