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4. Fernando Torres (Liverpool to Chelsea, £50 million)
There was a time when Fernando Torres was one of the most feared names in European football. Having signed for Liverpool in 2007, Torres built a near-telepathic relationship with Steven Gerrard, his goals helping him to third place in the 2008 Ballon d’Or.
His form dipped in the 2010-11 season, but that did not stop Chelsea from stumping out an English record £50 million bid to sign him on the January transfer window’s deadline day.
However, much like the investment made on Andriy Shevchenko a few years previously, the money spent on Torres bore little fruit, as the Spaniard was never able to rediscover the form that saw him become a cult hero at Anfield.
Still at Chelsea, Torres has time to repay the investment in him, but for now, his transfer still remains one of the biggest deadline day gaffes in the history of football.
