4) Cesc Fabregas - 2011
The Cesc Fabregas transfer saga was one for the ages. For two years Barcelona chased their prodigal son, with players such as Xavi, Carles Puyol and Gerard Pique also getting in on the act with comments in the press or antics such as putting a Barcelona shirt on him during Spain's World Cup celebrations.
Having joined the club as a teenager and spending eight years at Arsenal, Fabregas was indebted to Wenger for giving him his break and also handing him the captain's armband in 2008 when he was just 21.
Fabregas broke a few records in the Premier League and also became one of the best attacking midfielders in the league. But he yearned to return home and was torn between the love for Arsenal and Barcelona.
"I will be clear about this. Fabregas is with Arsenal for a very long time and he will stay." - Wenger in July 2011
Sadly, Fabregas had made up his mind by then. When he had the chance to leave in 2010, he chose to stay. But Arsenal were not making any progress while Barcelona were the best team in the world having won two Champions League titles in three years.
Fabregas was gone a month later for a fee in the region of £35m.