Boasting a perfect record of four wins from four competitive games on his return to Serie A, Mourinho is enjoying his time in the Italian capital. But the initial bounce of his arrival has been seen time and time again, much like its eventual decline as cracks appear in his armour.
However, the new emperor of Rome has gone back to basics for his latest career challenge. His ambitions in his previous roles with Chelsea (twice), Internazionale, Real Madrid, Manchester United and Tottenham Hotspur were fuelled by a hunger for trophies. But there's now a different goal for the man from the Portuguese city of Setubal.
Mourinho turned 58 at the start of the year. At the time, he was under pressure at Tottenham Hotspur. In April ,he was sacked having failed to deliver the success that inspired chairman Daniel Levy to invest in his appointment to complement Spurs' impressive and expensive new stadium.
A serial winner in his younger years as coach, Mourinho made his name as he defied the odds to lead Porto to UEFA Champions League glory in 2004. That success changed the direction of his ambition, and opened a new chapter in his coaching journey. For Mourinho, becoming a European champion set a new standard for his career.
Different ambitions define Jose Mourinho's story
Before that success, the ambition for Mourinho was to prove himself. Having failed to make the grade as a professional player, his coaching journey began without the backing and platform of a notable playing career.
Working alongside the late Sir Bobby Robson and Louis van Gaal as a translator at Barcelona, Mourinho had to prove his worth. But his confidence and self-belief ensured his presence was felt at the Camp Nou.
Mourinho had his chance with Benfica in September 2000. He won six of his 11 games, and departed before the end of the year. Unimpressed with the personality that had earned him the position in the first place, it was clear that those at the helm at Benfica were afraid of the power and influence Mourinho was quickly establishing for himself at the club.
Benfica's loss was Uniao de Leiria's gain, and Mourinho's dedication to proving himself brought the success that attracted Porto to his obvious and unique talent. His hunger for success was not just about achieving trophies, but about proving wrong those who had ever doubted his credentials.
Mourinho quickly understood that his players were key to his success. His infectious passion and determination ensured the entire changing room was right behind him.
Even though the ambitions from his time in Portugal switched to silverware by the time he arrived at Chelsea and Internazionale, the relationship with his players continued to be the catalyst to his success.
Having proved himself as the self-proclaimed 'special one' following his success with Porto, Mourinho now had a taste for silverware. While his appetite had changed, the tactics of the hunt remained the same.
Real Madrid followed. But a combination of factors meant that the power of his approach to the changing room was no longer as effective.
Reflections of success and failure
It will be a poignant moment for Mourinho when he steps out at the Stadio Olimpico on Sunday evening.
Despite his traditional public statement of throwing away medals once success has been achieved to focus on the future, he will allow himself a moment of reflection. His mind will return to his time at Barcelona and his appointment at Benfica more than 20 years ago.
The reason why he will reflect on those early years this weekend more than ever before is that his appetite has regressed to needing to prove himself to the world.
His dismissal from Tottenham Hotspur without a trophy will have affected him more than any other departure. He will have taken the criticism and questions over his ability to adapt to the modern game personally.
AS Roma have offered Mourinho the opportunity to achieve reputational redemption. While silverware will be a crucial part of his long-term remit, there is a bigger project that requires planning and patience to implement it effectively. Mourinho should achieve his ambitions with his new club, but success this time does not necessarily mean another trophy anytime soon.
Mourinho has cut a frustrated figure in recent years as his status in the game has been eclipsed by the younger coaches who were inevitably inspired by him. Understanding what he needs to achieve personal and professional peace this time around will change his character. Building a platform for a brighter future for I Giallorossi will deliver the redemption he needs at this stage of his managerial career.
He may be 1,000 games down the line. But the Mourinho, who will stand on the sidelines Sunday, will resemble the ambitious young coach at Benfica in September 2000 now more than ever before.
The game has changed, and Mourinho has also changed with it. But it is this hunger and ambition that has made him the man he is today.
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