#6 Jaap Stam
Dutch centre-back Japp Stam joined Manchester United in 1999 for £10.6 million, becoming the most expensive Dutchman in football history back then. However, an association which was worth lasting a decade ended when the defender was controversially sold to Italian outfit Lazio three years later.
Sir Alex was reportedly furious with some of Stam's claims in his autobiography. This led to a row between the gaffer and him, which paved the way for the Dutchman's move to Lazio.
Years later, Sir Alex expressed his regret over the decision stating, 'When I think of disappointments, obviously Jaap Stam was always a disappointment to me, I made a bad decision there.'
As for Stam, he didn't win enough silverware to match his exploits at Manchester United. Had he stayed, his name would have certainly gone down in the club's hall of fame.