When James decided to quit the Bernabeu earlier this summer, it was Ancelotti who awaited the former Monaco man with open arms. The Italain managed to convince the midfielder to swap Madrid for Munich in their joint quest for success and silverware.
In the summer, there was no reason as to why that quest would not be successful, but just a few short months later and Ancelotti is out of the door, leaving James with a head full of doubts and with a lot to prove once again.
Ancelotti did everything to make James feel at homein Bavaria, even going so far as to accompany the Colombian to his presentation. This was his star signing, the player that was going to fire Bayern to Champions League glory, finally!
When the pair previously worked together at Real Madrid, James scored 17 and laid on 18 more in his first season with 'Los Blancos', however, when Ancelotti departed the Bernabeu, James' form and confidence soon deserted him.
Neither Rafa Benitez or Zinedine Zidane appeared to fully trust or rate James, leaving the star bereft of confidence and way short of his best.
Ancelotti took advantage of this predicament to put together complex deal (a two-year loan with an option to buy) to bring the player to the Allianz Arena.
Despite an early knock, James quickly returned to fitness and looked to be establishing himself as a key part of Ancelotti's plans.
A fine performance against Wolfsburg in La Liga showed plenty of promise, but the player was given the hook at half-time in the defeat to PSG on Wednesday that proved the final straw for Ancelotti.
James has now lost a manager that had complete and utter faith in his abilities and must now prove himself again in a foreign league, with a new manager and a new style of football.
Will he be successful?