4) Ezekiel Fryers
Ezekiel “Zeki” Fryers might possibly be the most controversial youth player to leave Manchester United in the past few years. The Manchester-born left back was admittedly not the biggest loss to United. In fact, there were already rumours floating about that United might put the player on the market following his refusal to sign a new contact, with the offered wage being the bone of contention. After joining United as a 16-year old in 2009, Fryer’s progress was steady, albeit not extraordinary. He was given his first senior team appearance as a starter in the League Cup match against once-bitter rivals Leeds United in 2011. As Fryer’s contract ran down, Tottenham Hotspurs emerged as the front-runners in acquiring the young fullback’s signature. United, however, wanted £6 million for the youngster under the FA’s youth compensation rule and in the end, Tottenham pulled out. Fryers eventually moved to Standard Liege for a minimal price under Belgium’s compensation laws. It seemed that that was the end of it, but Fryers then moved to Spurs in the January transfer window for £3 million in a move that was called “a blatant manipulation of the rules” by then United manager Sir Alex Ferguson.