#4 Robinho to Manchester City, 2008
This one wasn’t bizarre, clunky or cringe-worthy, but it was certainly a major embarrassment to Manchester City as they unveiled their biggest ever signing on transfer deadline day at the start of the 2008/09 season. Newly minted with Abu Dhabi money, it was known that City were willing to spend big, but this transfer took everyone by surprise.
Brazilian forward Robinho was apparently so unhappy at Real Madrid that he’d cried in the office of club president Ramon Calderon as he demanded a transfer. And he had a suitor in the form of Premier League giants Chelsea, who looked set to sign the Brazilian before the transfer window closed shop until January 2009.
They hadn’t counted on City’s takeover though, and suddenly their move was gazumped and Robinho ended up in Manchester and not London. The only problem was that nobody had seemed to tell the Brazilian this. In his first press conference to announce the British record £32.5m move, he explained to the press that he was glad that Real had accepted the offer from Chelsea – before someone pointed out the gaffe and Robinho was forced to correct himself – Manchester, not Chelsea.
The mistake made a lot of people – Pele included – suspect that Robinho’s move was motivated purely by the money on offer, and while City have since gone on to a lot of success due to that money, the nouveau riche image that Robinho’s gaffe presented with them has never really gone away.