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ESPN3 11:45 AM UTC
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Man United's Jose Mourinho faces biggest game of his career vs. Tottenham

Jose Mourinho faces the biggest game of his managerial career on Monday. Forget the Champions League finals and title deciders -- when Manchester United take on Tottenham at Old Trafford, the end result will be crucial for the one-time "special one."

Anything but a victory for the home team, and the doubts over Mourinho's ability to recreate his and United's glory days will only grow. He is approaching a crossroads, not only in his journey at Man United but also in the context of his overall record as a manager.

Mourinho has forged a blue-chip reputation as one of the leading coaches in world football. When he took charge of United in the summer of 2016, at the same time as Pep Guardiola's arrival across town at Manchester City, the former Porto, Chelsea, Inter Milan and Real Madrid manager was regarded as the only man who could compete with the former Barcelona and Bayern Munich coach.

They were two men who shared the summit of the game, but just over two years on, Mourinho is beginning to look like yesterday's man in comparison to Guardiola.

At City, Guardiola has built one of the most exciting teams ever seen in English football -- a team that broke countless records on the way to winning the Premier League last season, including becoming the first to smash the 100-point barrier.

They have started in similar fashion this season, but United, who finished second last term and won no trophies, have already stumbled and fallen after just two games of this new campaign.

Sunday's 3-2 defeat at Brighton following a shambolic performance at the Amex Stadium capped a turbulent month for United and Mourinho that has seen the manager and club in the headlines for all the wrong reasons.

There has been negativity and public displays of unhappiness from Mourinho, both during the preseason tour and then back in Manchester, a series of thinly-veiled criticisms of his Old Trafford bosses and high-profile players, including Paul Pogba and Anthony Martial, and, to cap it all off, two unconvincing displays at the start of the Premier League season.

The Brighton defeat was preceded by a 2-1 win at home to Leicester, but while City, Liverpool, Spurs and Chelsea have all raced out of the traps in emphatic style, United's form has matched Mourinho's mood: grey and miserable.

All of the above has led to an air of discontent at Old Trafford, which is why the Tottenham game has become so big for Mourinho.

Questions are now being asked about his future at United. Some fans want him to go, others are turning their frustration toward the owners and Ed Woodward, the executive vice-chairman.

On the pitch, Mourinho's players are not performing as though they are wholly behind their manager and the supporters have grown tired of the football prescribed by the 55-year-old.

So can he banish the doubts and silence his critics by masterminding a win against Tottenham that would also prove he can turn the tide at Old Trafford?

The great managers -- and Mourinho has certainly been one of those -- always find a way to retrieve a difficult situation. Sir Alex Ferguson did it on countless occasions, while Guardiola also responded positively to finishing fourth in his first season at City by guiding the club to such an impressive title win last term.

But Mourinho, for all of his successes, has yet to prove that he can steer one of his teams out of a downward trajectory. Whenever the going has got tough in the past, he has generally parted company with his club before the storm clouds have cleared. He has yet to show he can motivate a group of players to climb out of the hole they find themselves in.

A win against Tottenham would be a sign that Mourinho can do exactly that, but a draw or defeat would merely be another example of him struggling to restart the engine.

A negative result would then throw United into a tough game at Burnley on Sept 2, with the air of crisis escalating and the questions over Mourinho's position getting louder.

Beating Spurs will not offer definitive proof that Mourinho is on course to turn things around at United, but he now needs to show he has that ability in his locker. Because if he doesn't, and it all goes sour at United, where will he go next?

To remain a world-class manager, you have to move with the times and prove that you have as many good days ahead of you as you enjoyed in the past. Right now, it is difficult to suggest that is the case for Mourinho. But a win on Monday would give us all a sign that he is still special after all.


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