The Colombia international, who turns 25 in July, is a supremely gifted footballer - hence why he finds himself playing for arguably the world’s biggest football club - but his attitude has reportedly been an issue for Los Blancos throughout this season, both for Rafael Benitez and his successor Zinedine Zidane.
While both the player and the powers that be at Old Trafford are keen for a deal to be completed this summer, Jose Mourinho may need convincing before giving the green light to sign the South American playmaker.
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According to the Times, there are two primary reasons why Mourinho doesn’t want to bring James to England.
First of all, the Portuguese coach fears the left-footed maestro doesn’t possess the physique required to flourish in the robust Premier League. Secondly, Mourinho harbours doubts about James’ work rate.
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As Juan Mata discovered during his time working under Mourinho at Chelsea, the 53-year-old likes his playmakers to be strong, quick and capable of helping out defensively.
Mata himself now faces an uncertain future at Old Trafford but it’s unlikely that James will come in as a replacement for the Spaniard this summer.
Riyad Mahrez is proof that small can succeed
Leicester City’s Riyad Mahrez has proved this year that you don’t need to be strong and tall to flourish as a forward in England’s top division.
However, the Algeria international - who was recently crowned the PFA’s Premier League Player of the Year - has led by example at the King Power Stadium with his work rate.
Mahrez admitted in an interview with BBC Sport earlier this season that if he doesn’t track back, he’ll be substituted by manager Claudio Ranieri. The same rules apply under Mourinho.
Given that Real Madrid would demand a fee close to the £63 million they paid AS Monaco for James after the 2014 World Cup finals, Mourinho may feel that signing the Colombian simply isn’t worth the risk.
Could Mata become Mourinho's playmaker?
There’s a small chance Mourinho may opt to give Mata another chance to prove himself next season.
The Spain international has scored 26 goals in 104 appearances for the Red Devils and reportedly wants to stay at Old Trafford, regardless of Mourinho’s impending arrival.
Would James be a hit or a flop at Manchester United? Have your say by leaving a comment below.