Aleksander Hleb
When: 2008
How much: £8m
Hleb electrified the Arsenal midfield with his incredible dribbling and vision (and low socks), but despite becoming the first and only Belorussian to play for Barca he achieved little else during his time there. He was sent on loan to Germany twice and Birmingham, hilariously, but his career never quite recovered upon his release and has spent the remaining years of his career touring eastern Europe and Turkey.