The Chilean has transformed Manchester City from dull pragmatists into a free-scoring juggernaut but overcoming the 'Special One' represents his toughest challenge to date
It's showtime on Monday night and Jose Mourinho has accepted his casting as the pantomime villain.
It might be second against third when Manchester City face Chelsea at the Etihad Stadium but one of these two sides will be the Premier League champions this season. Arsenal have done an excellent job as the pacemaker but the trophy will head to either Manchester or west London in May.
City are the the people's favourites and have captured the imagination with their sparkling performances so far, breaking the 100-goal barrier across all competitions and playing some exhilarating attacking football.
It has taken them six years and more than £600 million in transfer fees to get to this stage under their Abu Dhabi ownership. As they fight on four fronts, the summer managerial change has paid off.
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Pellegrini, remember, inherited a disaffected squad who finished 11 points behind United last season, played dull, predictable football and were the constant the focus of stories about dressing-room disharmony.
Now they have the neutral's vote and the Chilean has made City popular in a way that Mourinho never will with Chelsea. The Portuguese is happy to be the bad guy and he has made no attempt to hide his resentment towards City.
After all, Chelsea received little love from outsiders when they were accused of buying the title in Mourinho's first spell in charge thanks to Roman Abramovich's rubles.
"I don't know why they are so popular when we weren't. I don't know why," the Blues boss complained during his pre-match media duties. "In my time we were accused of buying the title, no? Because our owner was Mr Abramovich, just arrived in the country. Maybe now people see City in a different way."
Mourinho also threw in thinly veiled jibes over "lucky" decisions that have fallen in City's favour this season, as well as a moan over City's "dodgy" compliance with Uefa's financial fair play regulations.
Yet both clubs are in this situation thanks to huge wealth that has allowed them to blow competitors out of the water in attracting some of the world's best players to their clubs.
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While City and Chelsea have used similar approaches to first challenge and then overtake the more traditional powers in English football, Monday night's match in east Manchester will represent a significant clash of on-field styles.
If Pellegrini is the artist, Mourinho is the pragmatist. He joked after the goalless draw with West Ham on Wednesday that Chelsea needed a Black & Decker drill to break down the Hammers' defence but the Portuguese's teams themselves play like a mechanical tool. They grind teams down with power and resilience until they find a moment of weakness.
For all their attacking talent, however, the Blues are nowhere near Monday's opponents when it comes to ease on the eye and attacking aesthetics.
With the two teams separated by just three points, Mourinho has proved that there are different ways to skin a cat and it is nothing new to him, having rejoined Chelsea after spending three years challenging Barcelona as the coach of Real Madrid.
Many people may still be waiting for Chelsea to click into gear but Mourinho knows how to get the job done. He has played for - and achieved - away draws at United, Arsenal and Tottenham this season and will likely travel to the Etihad with the same objective.
Mourinho is a real winner and knows that there are still another 42 points for which to play after Monday's game. It represents the biggest challenge so far for Pellegrini and, if anyone is going to work out how to stop City, it will be Mourinho.
It may mean that the visitors stifle the game and attempt to turn it into a borefest, packing men behind the ball and rarely committing more than three men to attacks. That may not play too well with viewers but Mourinho isn't fussed about popularity contests anyway.