2. Alan Shearer
Destination: Blackburn and Newcastle Nowadays, Alan Shearer is known to us all as a bald Newcastle United legend, but back in the 90s, though, Alan Shearer was more recognisable as a balding goal machine. He is slightly unique to everyone on this list as he actually turned down Sir Alex Ferguson at two different stages in his career, chosing Blackburn Rovers over United in 1992, and then in 1996 he opting for his boyhood club Newcastle, as Fergie again was left wanting. The debate that generally comes with Alan Shearer's career surrounds whether or not he would personally regret missing out on years of silverware at Old Trafford. He always claims he wouldn't change a thing about his career, and you would have to believe him. He is a Newcastle Icon, achieving a status there that he probably wouldn't have done at United, instead being remembered as a part of one of Ferguson's great sides. He also has the memories of pipping United to the title in 1995 with Blackburn Rovers. For Ferguson, although he missed out on the signing of Alan Shearer for a second time in 1996 and has since then spoke of his regret in missing out on the Geordie frontman, he did bring in Ole Gunnar Solskjaer for just £1.5 million, 10 times less than the cost of Shearer. Solskjaer would go on to to become a United legend, famously scoring the winner in the 1999 Champion's League final as well as winning 6 league medals with the club.