5 major January transfers that collapsed at the last minute

4. Kaka – AC Milan to Manchester City (2009)

Manchester City were reportedly willing to spend £100m on Kaka in 2009

Newly minted with a seemingly unlimited amount of money following the club’s buyout at the hands of the Abu Dhabi Group in the summer of 2008, Manchester City were determined to show the rest of the football world that they meant business, and they immediately flexed their financial muscles by breaking the British transfer fee record to sign Robinho from Real Madrid for £32.5m.

The following January, they attempted to make a move that would’ve been truly jaw-dropping by anyone’s standards. City set their sights on Brazilian forward Kaka – then of AC Milan and widely recognised as one of the best players on the planet – and were seemingly determined to bring him to the Etihad, reportedly offering in excess of £100m for the player.

However, despite City supposedly promising to pay the Brazilian a monstrous £500k per week, the move fell apart when Kaka chose not to push for a move away from Milan. The Serie A club stated that they were delighted to have kept the forward, who told Milan’s television channel that he’d chosen with his heart and hadn’t considered the money.

Kaka would eventually move in the summer of 2009 instead – but rather than heading to Manchester, the Bernabeu was his destination, as Real Madrid parted with €67m to finally prise him away from Milan.