1. Paul Gascoigne
Destination: Tottenham "Alan Shearer is one I wish I'd signed, but for me the most disappointing of all was Paul Gascoigne. A quote from Sir Alex Ferguson in 2008, on a player viewed by many as the most talented of his generation. Fergie famously went on holiday believing the deal to sign Gazza was more or less completed only to return and find that Tottenham had hijacked the deal at the last minute. Alas, Fergie was to miss out. One can only wonder what might have been for Gascoigne had he joined Fergie's ranks. Ferguson has said before that he feels some of the older Geordies that were in his team, people like Bryan Robson, might have helped to instil more discipline into Gascoigne. The late 80s at Manchester United are remembered most for Ferguson's arrival and immediate tackling of the drinking culture at the club. But this is impossible to tell, really. The clubs Gazza chose throughout his career were more than likely always going to be unable to prevent his off the field problems. He would go on from his rejection of United to have a good spell with Tottenham, helping them to an FA Cup win in 1991, followed by spells at Lazio, Rangers, Middlesborough and Everton. While he made 57 appearances for England and nearly 400 appearances overall in his club career, his mammoth potential was never fulfilled due to his relentless battle with alcoholism and mental illnesses. Sources:
Telegraph