The Nine Worst Transfers Of The Calender Year, With Big-Money Liverpool And Man United Flops

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8) Jermain Defoe (Tottenham to Toronto FC)

Jermain Defoe Toronto

Despite offers from several Premier League clubs, Defoe chose Toronto and the MLS after leaving Tottenham. The former England international subsequently cost himself a spot at the 2014 World Cup, and has endured a frustrating spell in the States.

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