1. Francis Jeffers
One of the most pointless transfers in the history of the game, Arsene Wenger bought in Francis Jeffers from Everton in 2001 to supposedly add a cutting edge to the Arsenal attack, even though they had a certain Frenchman leading the line at the time. It is no great surprise that he didn’t set Highbury alight, as he only managed 4 goals in 22 appearances for the Gunners. It is also no great surprise that he was loaned back to Everton the season afterwards, and sold to Charlton the season after.