Is Manchester United Jose Mourinho’s Greatest Challenge?

Manchester United and Jose Mourinho have started off life together quite well thus far, already achieving their first piece of silverware and first Premier League victory this month.

Players in the squad have appeared to link up nicely together, and the arrival of French midfield star Paul Pogba will add another dimension to the club in the coming weeks.

The Special One has played this role before. The confident and brash new manager at one of the world’s most recognised and storied teams is not something new to the Portuguese tactician.

As manager of FC Porto (Portugal), Chelsea (England), Inter Milan (Italy) and Real Madrid (Spain), Mourinho has seen and learned from some of Europe’s top football leagues and managers. He has adapted his tactics and approach to each league he has worked in.

Real Madrid and Chelsea both presented unique situations and expectations.

But will Manchester United provide him with his greatest challenge yet?

We look at why this could well prove to be Mourinho’s toughest appointment, and how he is likely to get on in the near future.


Specifically looking at his managerial positions at Real Madrid, Manchester United and Chelsea, some similarities stand out.

One factor that is common among all three clubs is financial backing – a lot of financial backing.

Real Madrid president Florentino Perez, the Glazer family and Roman Abramovich are all examples of owners who aren’t shy when it comes to spending money and are constantly looking to improve their squad year after year.

In this sense, Mourinho has always been able to have a top quality roster. Each of the three teams had talent in place and a transfer budget that will allow for significant improvements to be brought in.

From Cristiano Ronaldo to Didier Drogba, all the way up to the present day with Zlatan Ibrahimovic and Paul Pogba, Jose has always had some of the world’s finest footballers at his disposal.

Expectations were similar across these three clubs as well. Success is a given, and all three ownership groups were looking for multiple trophies each and every season. These expectations were only enhanced by what Mourinho brought to the table as well.

Champions League crowns, domestic cups and league titles from all over Europe glitter Jose’s resume. Because of this, Mourinho is rightly considered one of the world’s best managers, and as such, he is expected to lift the standards of even the world’s very best clubs.


Los Galacticos are arguably the biggest club on the planet. Despite unprecedented history and massive expectations from the fanbase, Mourinho was able to achieve some success during his three seasons in charge from 2010-2013.

A La Liga title, one Spanish Super Cup and one Copa del Rey were impressive, but not impressive enough for a club that expects all of that in one season.

What Mourinho faced in Spain was certainly unique and presented one of his greatest challenges. While one could make the case that the English Premier League is more competitive from top to bottom than Spain’s La Liga, Real Madrid was up against one of the greatest Barcelona teams in football history.

Manager Pep Guardiola, Lionel Messi, Xavi Hernandez and Andres Iniesta were a constant thorn in Mourinho’s side and provided difficulty for Real Madrid in every competition during his time in the Spanish capital.


Jose Mourinho and owner Roman Abramovich had two very successful stints together with Chelsea, originally from 2004 until 2007 and then more recently from 2013 to 2015. During his time in charge of the Blues, Mourinho ushered in a new wave of success for the club and firmly established them at the top of the Premier League hierarchy.

Three Premier League titles, three League Cups, a Community Shield and an FA Cup were all captured while the Portuguese manager was in charge.

Though his achievement of delivering the first division title to Stamford Bridge for the first time in 50 years was outstanding, his second spell at Chelsea was perhaps a more difficult challenge, given the raised expectations and his return to work with Abramovich who had previously forced him out of the club.

Russian billionaire Roman Abramovich bought the team in 2003 and began going on lavish spending sprees for players. After “The Tinkerman” Claudio Ranieri was dismissed and Mourinho put in charge, the club began an incredible period of success.

Despite great competition from the likes of Manchester United and Liverpool at the time, Chelsea were able to dominate.

Mourinho’s second stint, however, came a time where the Blues were in need of rescuing and lifting back to the top. While Mourinho managed to do exactly this and won the double in 2014/15, it ultimately came at a price as he was again sacked from his role at Stamford Bridge in late 2015.

The challenge of repeating or accomplishing more proved to be too much for Jose and a player mutiny led to dreadful results.


Sir Alex Ferguson’s retirement was never going to lead into an easy transition for Manchester United. David Moyes and Louis Van Gaal tried to bring the same success to Old Trafford and ultimately failed.

Mourinho now takes over a squad that has been unable to bounce back to former glory recently.

While Jose is undoubtedly prepared for his new challenge, the Premier League has changed considerably even during the few months he has spent out of the game since his Chelsea departure.

Leicester City are the surprise Champions, Pep Guardiola, Antonio Conte and Jurgen Klopp have now all had a pre-season with their respective new clubs and the standard of players in the division appears to be growing once again. In Europe, a Champions League title can be even more elusive thanks to the exploits of Barcelona, Real Madrid and Bayern Munich.

He and the club have begun well, but the path to success is a long and winding road.


Each of the various positions highlighted come with intense pressure, and Jose Mourinho knew that well before hand. He enjoys a challenge and loves to build a new squad with quality players.

His major triumphs normally take some time, as evidenced by his need to reshape and reorganise what he has available in his lineup and team philosophy.

A Champions League title with FC Porto, a historic treble with Inter Milan, a La Liga title with Real Madrid and a Premier League championship in 2014-15 with Chelsea all took place during his second season in charge of the club.

The Special One needs time to craft his roster and find the best tactical approach to achieve the desired results, and this may be the case with his current role at Manchester United.

Manchester United will be Jose Mourinho’s greatest challenge because of the legacy set by Sir Alex Ferguson. Premier League and Champions League crowns are the only way to fulfil that legacy.

Is Mourinho up to the challenge? Only time will tell.


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