2) Samir Nasri - 2011
When Samir Nasri joined Arsenal in 2008, a lot was expected of the talented young French midfielder who had been drawn comparisons with Zinedine Zidane back when he was a little kid making his way up the ranks.
Scoring a winner on debut was just the start as Nasri became an integral member of the Arsenal attack, scoring a number of beautiful goals in various competitions. But that was when Manchester City were luring players from Premier League rivals in an attempt to find instant success and Nasri was one of their targets.
Nasri was also in the final year of his contract but Wenger said he was 'clear' on the player's future.
"Samir's situation is clear for me. He stays. we are in a position where we can say 'No'." - Wenger in July 2011
Nasri started the season with Arsenal but he also made it clear to Wenger privately that he wanted to leave. The significantly higher wages were also too good to turn down.
City soon signed the Frenchman a week before deadline day for a fee in the region of £25m. And one of his reasons for moving was that City fans were "really passionate" compared to the crowd at the Emirates.