Left Midfielder: Andrei Arshavin
At the end of the 2009 January transfer window, Arsenal did something that is very out of the ordinary for them. They signed a player on the last day of the window, and who they signed has probably put Arsene Wenger off doing the same thing again. The Russian Andrei Arshavin made a real splash at Euro 2008 and with his work at Zenit St Petersburg, so when he signed for the club
for around £15 million was seen as a superb piece of business. And in his first six months at the club, it looked as though that prediction was accurate, with some astonishing performances aptly demonstrating his sleek touch and skill. This was best displayed with his four goals against Liverpool that made him look like one of the best signings in the club's history. But at the start of the next season, he looked a completely different player in the worst possible way. He seemingly couldn't get used to the pace of the games and the frequency of the matches. Injuries and inconsistency started to creep in that made him appear a shadow of the player that he was at the start of his Arsenal career. He began to lose his place in the squad to pacier wingers, and would eventually be sent back to Russia. His return of 31 goals and 41 assists in 143 appearances was certainly not terrible compared to others on this list. However, his signing did prove to be a disappointment, as compared to what he showed he could do in early 2009, he never was able to produce at the level that Arsenal needed him to perform at.
Other contenders: David Grondin, Alberto Mendez