Kevin de Bruyne (At Chelsea)
This is perhaps one of the most regrettable decisions Mourinho has made as Kevin De Bruyne is now one of the most prolific playmakers in football.
The Belgian failed to get himself on the Blues team under Mourinho with the manager famously firing a dig at the young player saying, "With De Bruyne, if you have a player knocking on your door and crying every day he wants to leave, you have to make a decision...But if he was at Chelsea and not at Wolfsburg, he wouldn't have reached this level. It was like a wall, a block. He was not ready to compete. He was an upset kid, training very bad."
The Belgian was eventually sold in a cheap transfer to Wolfsburg, where he impressed enough to become one of the Bundesliga's best attackers.
His performances saw him returning to England to join Manchester City in 2015 where he has performed considerably well with Premier League titles under his belt.