2. Past Relationship With Roman Abramovich
Considering the relationship between Mourinho and owner Roman Abramovich was so fraught when the Portuguese' left the club in 2007, there is huge uncertainty as to whether a second working relationship would even be tenable. Owner and manager were like chalk and cheese at the time and it perhaps came as very little surprise that their frosty relationship culminated with Mourinho's departure given the underlying context. It is suspected Mourinho was given his marching orders because he refused to play flop Andriy Shevchenko - a close personal friend of Abramovich who cost the club an alarming £31 million - while there were also tensions regarding transfer funds. If a manager loses his job based on his team selection, then you know something isn't right. The Russian Billionaire is known for his commanding, possessive nature and reluctance in letting manager's stamp their authority on a team, which means a relationship with someone as abrasive as Mourinho is never going to work out. Six years have passed, tempers have cooled down, water has trickled slowly under the bridge, but the wounds are still fresh, and Mourinho won't forget the way he was treated by the oligarch any time soon.