#4 IAN WRIGHT
Over the years since his retirement from the game in 2000, Arsenal legend Ian Wright had garnered fame in the UK as a TV & radio personality, featuring mostly as a football pundit, as well as in various football-related shows.
However, over a decade later, the former England international made a surprise switch to coaching. In 2012 Wright took the job at MK Dons, from the third division, on a part-time basis due to TV commitments. He only lasted a season before finally putting in his papers, having failed to fulfill Dons' promotion ambitions. Following the resignation, he was approached by fellow competitors Swindon Town but he refused, citing that he didn't want to be burdened with clubs hungry for promotion in the first season itself. Wright reverted back to media where he still is to date. In hindsight, Wright took too long to think about coaching, hence he struggled in the transition.