#3 Luke Shaw
Shaw was bought as a teenager from Southampton for a record fee for a teenager. A broken leg, a recovery period, and two seasons later, the 22-year-old English international's development has seen a stunted trajectory.
A huge part of what seems to be a campaign of "tough love" treatment from the manager, the player has been criticized publicly by Mourinho numerous times. So much so that reports suggested teammates felt the youngster was "bullied" by the manager following his halftime substitution and post-match chastisement for not following tactical instructions.
The verbal criticism has not been without an equal measure of game time, showing the gap in trust between player and manager that has not improved in Jose's two-year tenure. Shaw has started only 7 league matches this season, far below what is necessary for the development of a young player once thought to be a future Three Lions star.
Mourinho has also criticized his fitness and commitment. A criticism that four different managers have leveled at the player in his short career thus far.
Many of these issues existed for the player that there is now a vibe of "now or never" for Shaw - a vibe that is reportedly moving towards "never'.