3. Paul Gascoigne
ROBERTO PFEIL/AP/Press Association ImagesIn the mid-to-late eighties, Paul Gascoigne was one of the biggest draws in world football, tipped to go on to become one of the modern day greats. Unsurprisingly then, Manchester United were keen on acquiring his services and signing him from first club Newcastle United. In an inexplicable moment of madness, however, the then-21-year-old opted to reject Sir Alex Ferguson in favour of joining Tottenham Hotspur. Though Gascoigne won the FA Cup with Spurs in 1991, his time at White Hart Lane was ruined by injury, and the eccentric Englishman later admitted
he should have joined United, and that one of his greatest regrets was not doing so. 'Gazza' could have won untold trophies at Old Trafford, and may have gone on to become one of the club's all-time greats. Realising his mistake, he tried to resurrect a move to United later in his career, but by then Fergie was no longer interested. Many pundits have wondered if the former midfielder's well-documented problems with alcoholism could have been avoided had he joined United, and whether Ferguson could have guided him down a less destructive path than the one he would unfortunately end up taking.