The good, the bad and the ugly: Jose Mourinho’s memorable managerial moments

Jose Mourinho added a fifth European title to his trophy cabinet on Wednesday, but for all his success as a manager, the Portuguese boss isn't without his fair share of drama.

Jose Mourinho's burst onto the managerial scene took the sporting world by storm. His unrivalled charm and arrogance was justified through his ruthless pursuit of success, and it was quick to catch the eye of fans around the world.

With stints at Benfica, Porto, Inter Milan, Chelsea, Real MadridManchester UnitedTottenham Hotspur and now AS Roma, Mourinho's European road trip has seen him become one of the world's most prestigious managers.

But despite winning eight league titles and five European trophies in his career, when Mourinho is brought into conversation, it's usually dominated by his controversial moments and antics.

Following on from his latest European triumph with Roma, Planet Sport takes a look at the good, bad, and ugly moments of Mourinho's managerial career so far.

The Good

Landing on his feet

After enduring the first trophyless stint of his managerial career at Tottenham, Mourinho looked to be on the decline, with many considering his tactics to be outdated for modern football.

But just one month after facing the sack in north London, Mourinho jetted off to Rome to embark on a new adventure, and he silenced his critics within his first season at the club.

A sixth-placed finish in the league didn't exactly steal the headlines around Italy, but Mourinho's run in Europe certainly did. In the inaugural Europa Conference League tournament, the 59-year-old navigated his side to the final, where Dutch side Feyenoord awaited.

With Roma having never won a European title, it was undoubtedly one of the club's biggest games, despite the Conference League holding less prestige than it's bigger continental brothers.

And the Italian side lifted the trophy under Mourinho after a 1-0 win, with Nicolo Zaniolo scoring the only goal of the game in the first half.

It was Mourinho's fifth European title as manager, extending his 100% winning record in continental finals, while also making him the first manager to win all three European competitions.

Old Trafford Celebrations

Many consider this the start of football's love affair with Jose Mourinho. After initially starting his managerial career at Benfica in 2000, Mourinho resigned following a dispute with the club president and instead took charge of Portuguese rivals Porto in 2002.

Mourinho's flair and arrogance was there for all to see, proclaiming in his first season that he "would make Porto champions" the following year.

But Mourinho backed his message on the pitch, taking Porto from fifth place in the Primeira Liga to league champions the following season, breaking the points record in the process.

However, while Mourinho had already impressed in Portugal, it wasn't until the following season that he announced his name on the global stage.

In Porto's 2003/04 Champions League campaign, Mourinho's side were drawn against reigning Premier League champions, Manchester United, in the round of 16.

After beating United 2-1 in the first leg, everything came down to the clash at Old Trafford, and Mourinho's side didn't disappoint. After scoring an 89th-minute equaliser, Porto led 3-2 on aggregate and the Portuguese went flying down the Old Trafford touchline in, what we now know as, typical Mourinho fashion.

The celebration split opinion, with some lauding it as a great show of passion and spirit, whereas others considered it a show of disrespect and arrogance. Strangely enough, 17 years on, discussions about Mourinho follow a similar trend.

The victory against Manchester United proved significant, with his Porto side going on to defy all odds and win the Champions League that year, well and truly etching Mourinho's name into soccer history.

"The Special One"

Following his record-breaking spell at Porto, Mourinho's Champions League success meant he was ready for a step up. At first, Mourinho looked favourite for the Liverpool job, but after discussions with new Chelsea owner Roman Abramovich, Mourinho pledged his future to the London side.

After the win over Sir Alex Ferguson the previous year, many wondered whether his new team could challenge Manchester United at the top of the Premier League. After his opening press conference, nobody doubted it.

Unbeknown to him at the time, the words that Mourinho used that day would be used to shape his entire managerial career.

The "Special One" quickly became one of the most talked about figures in English soccer, even more so when he once again backed up his statement and won Chelsea the Premier League title in back-to-back years, before returning in the 2014/15 season and winning the title again.

Inter treble

After a series of disagreements with Chelsea owner Roman Abramovich, Mourinho departed Chelsea in 2007 and was appointed manager of Italian side Inter Milan.

In his opening press conference, Mourinho provided his usual dose of witty arrogance. After conducting the entire conference in Italian, Mourinho claimed it took him just three weeks to learn the language.

In his first season at the club, Mourinho continued his hot streak of winning silverware, this time claiming the Serie A title as well as the Italian Supercup.

But it was in the following season that Mourinho once again showed his dominance within European soccer. His Inter Milan side went on to win Serie A, the Coppa Italia, and the Champions League, becoming the first Italian side in history to complete the treble.

The Bad

Paul Pogba confrontation

Mourinho's appointment as Manchester United manager was met with a mixed response. For many United fans, the memories of him running down the Old Trafford touchline still lived fresh in their minds.

But with the club struggling to recapture their glory era under Sir Alex Ferguson, Mourinho looked the best candidate to bring back silverware to Old Trafford.

And, to be fair to him, Mourinho did just that, winning the EFL Cup and Europa League in 2016/17. Combined with a second place finish in the following season's Premier League, United under Mourinho seemed to be on their way back.

However, after a poor start to the 2018/19 season, everything seemed to go downhill for the Portuguese manager.

Maybe worthy of its own spot on this list, Mourinho returned with his usual outlandish charm, demanding "respect" from the English press, pointing towards his previous three Premier League titles as a reason to escape criticism.

But perhaps nothing sums up Mourinho's fall from grace at United more than his confrontation with French midfielder Paul Pogba.

After signing Pogba for a record transfer fee of £89million in 2016, Mourinho's relationship with the midfielder slowly deteriorated, and even resulted in a confrontation at the training ground.

It was thought to have occurred following an Instagram story posted by the midfielder which Mourinho believed was directed at Manchester United's defeat to Derby County in the Carabao Cup.

The clash also resulted in Pogba being stripped of the vice-captaincy at United, and the midfielder has recently opened up on his relationship with Mourinho, claiming he "didn't know what happened" to cause such a breakdown.

Eva Carneiro

The return of Mourinho to Stamford Bridge in 2013 seemed to be going to plan. The Portuguese manager continued where he left off, winning the League Cup and Premier League in 2015.

But in the very first game of the 2015/16 season, things started to turn sour. In a game against Swansea City, Eden Hazard went down injured, causing referee Michael Oliver to wave on the Chelsea medical staff.

But with Mourinho himself deeming the injury not worthy of medical attention, he reacted aggressively to his medical staff's attempt to enter the pitch.

In particular, Mourinho seemed infuriated by club doctor Eva Carneiro and the row between the duo dominated the front pages in the following weeks.

On the event, Carneiro said,

"I was in every paper in every country for a really long time and I wasn't at all comfortable with that. Certain individuals in football wanted to treat me like I did something wrong, when it was clear I was only doing my job." 

The event massively unsettled the Premier League champions and played a role in Chelsea's hugely disappointing season, which resulted in Mourinho being sacked just four months later.

Ashley Cole transfer

Following Mourinho's red carpet entrance at Chelsea, he quickly identified England and Arsenal left-back Ashley Cole as a major target at his new club.

Having been impressed with his performances, Mourinho and Cole met at a hotel to discuss a potential transfer, joined by Chelsea executive Peter Kenyon, and Cole's agent, Jonathan Barnett.

However, Arsenal were never made aware of such a meeting and therefore Mourinho and Chelsea were punished and accused of 'tapping up' a rival club's player.

All involved in the meeting were eventually fined, with Jose and Cole both coughing up £75,000 as a result of their secret meeting. Chelsea faced a £300,000 fine as well as a three-point deduction.

All in all, the whole saga hugely tarnished Mourinho's reputation.

But with Cole eventually completing the transfer in 2006, and going on to make over 200 appearances for Chelsea, it seemed Mourinho's controversial yet magnificent antics had once again prevailed.

The ugly

Wenger spat

When taking charge at Chelsea, Mourinho made it very clear that he was there to take over, but to do so, he had to dethrone London rivals Arsenal.

Inevitably, Mourinho clashed with Arsenal manager Arsene Wenger multiple times during his reign at Chelsea.

Even on the pitch, Mourinho's rigid, resolute and physical teams were a stark contrast to the flair and skill that encapsulated Wenger's Arsenal side - the narrative of Red vs Blue in London almost wrote itself.

But in typical fashion, Mourinho couldn't help but add fuel to the flame, consistently berating his colleague in the press.

The duo repeatedly went back and forth at one another, providing soap opera drama before the matches had even kicked off.

In one interview, Mourinho famously referred to Wenger as a "specialist in failure", claiming that if he had gone eight years trophyless just as Wenger had, he would "leave and not come back".

Frankly, the war of words between the two greats was just as enticing as their clashes on the pitch, but just as much as the feud was ugly, it was a masterclass of entertainment.

The 'Laundry Basket' incident

We couldn't help but add this one. In a remarkable sequence of events, Jose Mourinho hid in a laundry basket - yes, a laundry basket, to avoid a ban he received from UEFA.

Back in 2005, the then Chelsea manager received a touchline ban from UEFA following allegations he made towards Barcelona manager, Frank Rijkaard, in regards to influencing the match officials in Barca's 2-1 victory over the Blues.

With Mourinho's mind games at play, his Chelsea side went on to overcome the deficit in the second leg, progressing in the Champions League where they would next face Bayern Munich.

But Mourinho's comments cost him a two-game touchline suspension, a ban he clearly thought could be avoided through a bizarre plot to con the officials.

He arrived at the dressing room seven hours before kick-off, with the intention of seeing his players before their big clash. However, his escape from the stadium proved remarkably cartoonish and worthy of a Hollywood production.

Reflecting on the incident, Mourinho recalls the time he and his partner-in-crime kitman plotted his escape.

"I went there and nobody saw me. The problem was to leave after. And Stewart Bannister the kit man put me in the basket. It was a little bit open so I could breathe.

"But when he is taking it outside the dressing room, the UEFA guys were following and desperate to find me so he closed the box and I couldn't breathe! When he opened the box I was dying! I am serious! I was claustrophobic, I promise! It's true!"

However ridiculous and laughable the incident seems, Mourinho's men were once again victorious, beating Bayern Munich 4-2 on the night and progressing to the next round of the competition.

On paper, Mourinho disrespected and defied the authorities running the competition. But in reality, his scheming nature and relentless cunningness provided the soccer world with one of the most unimaginable sporting moments in history.

Intentional red cards

If the previous story didn't prove it already, Mourinho will do whatever he possibly can to make his team succeed. This was seemingly the case for his Real Madrid side in 2010 when he appeared to instruct Sergio Ramos and Xabi Alonso to pick up intentional red cards.

In their penultimate match of the Champions League group stage, Mourinho's Madrid side were cruising 4-0 against Ajax and had already qualified for the knockout stages.

Many managers would be content with the win and the performance, but Mourinho was busy thinking ahead. Alonso and Ramos were influential in the Madrid side and their pre-existing bookings threatened their chances of playing in the knockout fixtures.

Therefore, the only possible solution to wipe their slate clean in time for the fixtures was to have them suffer a red card. With the bigger picture in his mind, Mourinho, both ingeniously and outrageously, appeared to order his players to receive intentional red cards.

Perhaps even more surprisingly, the players didn't even try to hide their loopholing scheme, with Ramos even shaking the hand of the referee following his dismissal from the pitch.

Mourinho's antics once again saw his club face a fine, with Real Madrid forced to pay €120,000 for the event, while both players involved also faced €20,000 fines.

In more recent times, Real Madrid captain Ramos, tried to replicate the trick in 2019 by intentionally recieving a yellow card against Ajax in the Champions League. However, this time the Dutch team made him pay for his cheek by knocking out Madrid in the second leg of the tie.

READ MORE: Jose Mourinho describes Roma Europa Conference League success as 'immortal'

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