“There are lots of poets in football, but poets, they don’t win many titles.” José Mourinho has never been one to wax lyrical on the ideals and virtues of the so-called ‘beautiful’ game, his perspective epitomised by his thinly-veiled barb at the ‘poets’ that critique his own philosophy after lifting the Europa League in May 2017.

For as long as Mourinho has been in the footballing mainstream, starting with his unlikely Champions League triumph with Porto, his divisive nature has brought upon countless detractors that view him as a narcissistic dictator who will use any means necessary to ensure victory.

Whether that be through dark psychology or overt pragmatism, it is evident that Mourinho has gone further than any manager before him in search of glory, much to the disapproval of the romantics and purists of the game. However, there is a man who would advocate and encourage Mourinho’s leadership complex had he not been born 500 years ago: introducing Niccolò Machiavelli.

Machiavelli was a Renaissance diplomat, philosopher and politician among other careers who lived in Florence in the early 16th century. He was part of the Republic of his home city for 14 years, overthrowing the famous Medici family with his political acumen and rebellious nature before his exile from government in 1512. Following on from his tenure in office, Machiavelli set about writing works on his experiences in politics and the philosophy he had devised from this.

He released his first and most famous work The Prince the year after his exile, and it is from here that much of his influence in the modern world stems from. The Prince tackles the idea of leadership; how people come to be leaders and what makes them effective. What intrigued Machiavelli was the dilemma of whether somebody was capable of being a good leader and still adhere to Christian morality or, in other words, be a good person. Machiavelli concluded that it simply wasn’t possible.

He saw that the aim of leadership in politics was to protect your state from potential threat. To do this, one must know how to fight and do whatever is required to achieve his objective, even if these actions are seen as insidious or perfidious. A leader must also govern his people in a certain way to ensure order.

While Christians believed leaders should be gracious, generous and peaceful, Machiavelli saw these qualities to be weaknesses that could be exploited. Instead, he theorised that to rule effectively, one had to strike a balance between being feared for his strict regime but not being oppressive and loathed by his followers.

Machiavelli is one of the most consequential philosophers of all time because of this belief, inspiring countless intellectuals such as Karl Marx, Friedrich Nietzsche and Adam Smith. The term ‘Machiavellian’ still holds resonance to this day as a means to describe politicians who use underhanded methods to achieve their goals and his pragmatic approach can be compared in other walks of life, including football.

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This is where the connection between Mourinho and Machiavelli lies; the art of pragmatism. Football doesn’t have a strong correlation with philosophy but it has been said before that Mourinho is a Machiavellian leader and it would be hard to disagree. Mourinho, as aforementioned, is an unquenchable winner, it is his only purpose in football and he believes that winning should be the only objective of the game. This is why he objects to the “poets” who laud the importance of aesthetics as equal or superior to that of victory.

He is unapologetic in his methods that polarise the footballing community unlike any other: his enigmatic and cunning oration in press conferences that draw more attention than some Champions League games, the deviously intricate web of psychology he weaves to unnerve his opponents and drive his own team, and the “negative” football he masterminds in order to extract every last piece of silverware. These are all elements of his leadership style, the Machiavellian style. Mourinho has even acknowledged Machiavelli, saying in a Telegraph interview in 2015 that he had read some of the Italian’s work and was aware of the similarities with him.

In that very interview, however, Mourinho said that he wanted to put an end to his cunning streak and distance himself from the dark arts, so to speak. Three years on, it is a promise he has not kept.

The cult of personality that Mourinho has created to ingrain himself into the fabric of the sport has only become grander and more histrionic than ever, while the football his teams have produced has been at times direly cautious and restrained, like putting harsh, steel-bounded clamps on a flaming Ferrari. Well, at least, he’s winning things, right? Alas, Mourinho’s get-out-of-jail-free card has expired, the wondrous sweetness of silver and gold’s glorious kiss has degenerated into the biting cold of what seemed to be a never-ending winter at Old Trafford.

Gone are the heady days of Mourinho’s reign atop the world seated on his throne, the dashing and suave rockstar of the dugout. We now see a beleaguered man who seems to be confined by the past, seemingly obsessed with his persona rather than his success. The catch with Machiavellians is that unless their methods have the desired effects, they are not only ineffective but unnecessarily unscrupulous. As the world gawks at the passion and dexterity of the Guardiolas and Klopps, Mourinho is left out in the cold.

Signs of his spiral were beginning to come to the fore long before he arrived at Old Trafford; in fact long before he returned to England after a six-year hiatus. His time with Real Madrid, a job he had coveted from the beginning of his managerial career, had been tumultuous. Mourinho arrived in the capital of Spain the star of the show and left the pantomime villain after countless feuds externally, most notably with Pep Guardiola’s Barcelona, as he attempted to derail the all-conquering Blaugrana through venomous words and a vengeful approach – to kick, knock and scrap to victory.

Though Guardiola fended off Los Blancos to win a second Champions League trophy and LaLiga in Mourinho’s first year in Madrid, he left the following season exhausted after the unmatched war between the two juggernauts of Spanish football. That year, Mourinho and Real lifted their first LaLiga title in four years with a record number of points and goals scored, a battle won though perhaps not the war.

The Real vintage of 2011/12 was Mourinho’s final classic side, incorporating all the facets of their manager’s philosophy that had been so dominant in the previous decade. They were defensively stern, as every Mourinho team is, but were also by far his most potent outfit with an abundance of pace and power in their ranks that could obliterate teams in a blink of an eye.

With a strike force including Cristiano Ronaldo, Karim Benzema, Mesut Özil and Ángel Di María, Real were ruthless on the counter-attack in a way none of Mourinho teams had replicated and were packed to the brim of individual brilliance, perhaps more so than Porto, Chelsea and Inter, where the Special One had managed previously.

Read | José Mourinho and the dark triad at Real Madrid

But for all the prowess Mourinho had at its disposal, there was an issue that he had never faced before in his career. It is well-documented that the dressing room of Real Madrid is by far the most political in football, the dynamic of the world’s most famous team constantly teetering on the verge of chaos.

If the squad is kept happy, managers of Los Blancos usually reap the rewards – see Zinédine Zidane, who is now one of only three coaches to lift the European Cup three times. However, if there is disruption in the camp, it will largely be the undoing of the manager – see Rafa Benítez, who was sacked after just six months in charge despite being third in the league and just four points off the top.

Coming off the back of a hugely successful league campaign, the 2012/13 season was critical for Mourinho and Real in the hopes of winning La Décima, a historic tenth Champions League trophy, as well as continuing their domination of LaLiga. However, Real had faltered in the opening games as their eternal rivals Barcelona raced off the blocks, setting out an almost insurmountable lead by Christmas with a record start to a LaLiga campaign.

Perhaps disheartened by falling away from the runaway leaders, cracks began to show at the Bernabéu. Mourinho, it seemed, was almost paranoid over the power afforded to the players and began to feel like a rebellion was imminent.

To combat this, he delved into his Machiavellian bag of tricks to invoke fear into the dressing room in a bid to wrest back control. When he discovered that captain and club legend Iker Casillas had called Barcelona skipper Xavi to call for peace between the two warring sides of El Clásico, Mourinho had the perfect excuse to target a God-like figure and fully centralise power.

Added to this was the fact that Casillas’ girlfriend was a prominent journalist in Spanish media who could potentially leak information, a factor Mourinho was hoping to exploit. The Portuguese coach took the bold move to drop Casillas on numerous occasions around the turn of the year, replacing him with back-up keeper Antonio Adán and then signing Diego Lopez from Sevilla to further isolate Real’s number one.

This approach split the fan base: the Madridstas were outraged with the negligent treatment of “San Iker” whilst the Mourinhinstas believed the man at the helm was acting in the club’s best interests. One place where the verdict was unanimous, however, was Real’s dressing room. They were apoplectic with Mourinho’s decision, and the leading personalities in the side took action. According to reports, His relationship with Pepe, Sergio Ramos and Cristiano Ronaldo quickly deteriorated over the season, in part due to the controversy surrounding Casillas as well as other personal issues.

By May, continuing the fractious marriage between Mourinho and Real was incomprehensible. Florentino Pérez announced their parting of ways days after Real played in a turgid 2-1 defeat to city rivals Atlético in the Copa del Rey final. Los Blancos had also crashed out of the Champions League semi-finals for the third consecutive year, losing 4-3 on aggregate to a Robert Lewandowski-inspired Dortmund. Barcelona predictably triumphed in LaLiga, leaving Mourinho trophyless but for the Spanish Super Cup that was won at the beginning of the campaign.

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The man himself described the season “the worst of my career” shortly before his exit was announced. Three years previously, footage revealed Mourinho in an emotional embrace with Inter man Marco Materazzi when it was revealed he was leaving for the Bernabeu. Three years on, it was likely Mou’s departure was cause for celebration in the Real camp. For the first time, his Machiavellian ways had come undone.

Following the unceremonious departure from Madrid, Mourinho hopped on a plane to travel back to England, to the club where his impact is most felt. Since Chelsea cut ties with the Special One, the hot seat had undergone a phase of hot potato, a revolving door that had sprung seven new faces in six years.

The absence of their most successful manager had been felt, with the club in a constant state of flux in the demanding grip of Roman Abramovich. Mourinho was reinstated to bring some degree of stability to the club as well as deliver upon his guarantee of silverware. Unexpectedly, considering the miserable affair of his final days previously, José was all smiles at his first press conference. “I’m the happy one … I only came to love the club in time. This is a new feeling, arriving at a club where I love it already.” Mourinho wasn’t the only way in a fuzzy mood.

In the early days of the 2013/14 season, with the band – Frank Lampard, John Terry and Petr Čech – back together, the feel-good factor was rife at the Bridge. The second coming didn’t immediately translate to trophies, however, as Mourinho adjusted to a much-changed Chelsea squad.

There were some casualties as a result: Juan Mata, a hugely popular and talented member of the dressing room, came at odds with Mourinho due to disagreement on the latter’s philosophy. As we know, Mourinho is entrenched in his pragmatic approach and will not bend for anyone. A creative playmaker like Mata, even if they are talismanic in their influence, is surplus to requirements unless they are willing to devote themselves to the team and chip in defensively. After six months on the periphery, Mata was let go to Manchester United for £38m.

Alongside the high-profile sale of one of Chelsea’s best talents, a trio of fringe players were also sold to clubs down the footballing food chain in competitively discreet moves. Little was thought of the departures and Mourinho seemed apathetic in regards to them, yet later down the line, he would become far more concerned by the names Mohamed Salah, Kevin De Bruyne and Romelu Lukaku.

The year 2014 bore no fruits for Chelsea’s labour under their new master but they had managed to reach a respectable third in the Premier League behind Liverpool and Manchester City, as well as the semi-finals of the Champions League before succumbing to Atlético Madrid.

In a bid for the title on the second attempt, Mourinho shook up the Chelsea squad by letting club legends Lampard and Ashley Cole, whilst also selling David Luiz to Paris Saint-Germain for a record fee for a defender. He then brought in Cesc Fàbregas and Diego Costa, two men who had the potential to bring home the Premier League for the Blues, as well as the morale-boosting addition of Chelsea icon Didier Drogba from Galatasaray.

The astute work done in the transfer window resulted in the objective Mourinho craved: trophies. Two, in fact, as the Premier League and the League Cup were brought in to renew the club’s trophy cabinet. The league title was won in typical Mourinho style: race ahead early and then hold on to the opportunity with an unbreakable grip. The football Chelsea played, especially in the first half of the season, was exciting but it was the gritty side of Mourinho’s men that ensured the job got done, the mentality that the Special One had instilled in all of his teams up to that point.

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The low point of the season came in the Champions League, where Chelsea were knocked out by PSG in the round of 16 after a poor display. Mourinho’s chance to get his hands on Big Ears once again had been dashed for another season, but there were little doubts that he could muster a genuine challenge in his third season.

So what went wrong? What went so catastrophically wrong for Mourinho? Just seven months after confirming his third Premier League title, he was shown the door by the Chelsea board in one of the most dramatic falls from grace. A man who had never been officially sacked – though one has to wonder how mutual his departures from Chelsea in 2007 and Real Madrid in 2013 were – had been broken down by Christmas, leaving his club a point above the relegation zone. In a managerial climate as cutthroat as it is, it’s a wonder how he managed to make it to December, having been in an atrocious vein of form since the start of the season.

Away at Swansea didn’t seem like the birthplace of Mourinho’s downfall but circumstances were unorthodox at the Liberty Stadium. Rather than splashing the cash to build on a title-winning side, Abramovich had been unusually conservative with his spending, making no big-name signings in the summer transfer window, something that irked Mourinho.

There were links with a multitude of players that would have veritably strengthened the squad, including Paul Pogba, Raheem Sterling, Gareth Bale and John Stones. Any of these names would have not only added quality to Chelsea but competition in the dressing room, a major factor in a successful title retention. This wasn’t the first or the last time Mourinho, who signed a new four-year contract on the eve of the season, took issue with transfer business, but in retrospect, he had every right to do so.

The game itself was also unfamiliar: Chelsea drew with the Swans after an equaliser by Bafétimbi Gomes. As a result of this, Chelsea became the first team looking to retain their title to fail to win on the opening day in Premier League history. The headlines, though, were directed to an even more unexpected event: the row between Mourinho and club doctor Eva Carneiro. Mou has never been shy of picking fights but clashing with a fellow Chelsea employee for doing her job was a new low.

The reasoning was because she had rushed on to the pitch to treat Eden Hazard, who had gone down with a knock, forcing a stoppage in play. This infuriated Mourinho; Chelsea were on the counter-attack, with the Portuguese shouting “filha da puta” (“daughter of a whore”). A month later, Carneiro was sacked by the club after Mourinho criticised her in a post-match interview. She sued for unfair dismissal, which was eventually settled in June 2016.

The works of Machiavelli stated that a balance between discipline and respect had to be drawn but with this callous act, Mourinho had crossed the line between Machiavellian and tyrannical.

What happened from there is shrouded in mystery. What we do know is from that point, Mourinho’s authority in the dressing room weakened and, consequentially, results deteriorated. Defeats to the likes of Manchester City, Crystal Palace, Southampton, West Ham and Liverpool amounted to the worst Premier League start for the defending champions ever.

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The flames that had burned so brightly for the Blues months before had been extinguished, the likes of Hazard, Costa and Fàbregas going from game-changers to passengers in weeks. It became evident that Mourinho, once considered the master of man-management, capable of bringing players to a level above and beyond their imagination, had lost the dressing room.

When Chelsea were put to the sword by Leicester, Mourinho complained that “my work has been betrayed” by the players. Three days later, time was up for him due to “palpable discord with the players.” The fans who had worshipped him since 2004 were incensed and blamed the players for their lack of dignity by refusing to play for the manager. A banner was unveiled at the game after Mourinho’s sacking against Sunderland dubbing the aforementioned Costa, Hazard and Fabregas as rats.

Whatever the politics or intentions of that dressing room, Mourinho had now become the enemy of his own players twice. His next job would likely make or break his legacy, so where better than the Theatre of Dreams and the enticing pantheon of Manchester United?

The Red Devils were in a similar position to that of Chelsea before Mourinho returned. Since the retirement of the immortal Sir Alex Ferguson, United had been far below their lofty standards under David Moyes and his successor Louis van Gaal. The former was clearly out of his depth into the most demanding of hot seats, while the latter’s demise came from his frosty nature, both on the pitch with his negative style and off it with his prickly press conferences.

United recognised that they needed a truly world-class manager to fill the hole Sir Alex left, a man who wouldn’t be fazed by the scrutiny the role brought and could bring silverware back to Old Trafford.

Mourinho confirmed, through a new Instagram account, that he would be the next manager of Manchester United on 27 May 2016. It was a fresh start with a club he always had a great deal of admiration for. United were a rival that seemed, for the most part, to respect him.

He was unveiled at Old Trafford on 5 July, lacking the smiles of his return to Stamford Bridge. It was replaced by a stern, battle-hardened glare, and his press conference had no remnants of sentimentality that it did three years previously. The underlining message was that Mourinho was here to win. It had got to the stage at United that one word was all that mattered after three barren years attempting to reach the top four and lifting a lone FA Cup. Mourinho would, they prayed, do just that.

If silverware was the primary target of his first season, then Mourinho was an instant success. United won a treble of sorts, securing the Community Shield, the League Cup and the Europa League. They weren’t the ideal trophies for the United fans or board, but it kept them satiated for the time being.

There was also inspiration from the players brought in by the club. Indeed, the likes of Zlatan Ibrahimović, Eric Bailey and world-record signing Paul Pogba made the fans believe that United were a major player in the grand scheme of things once again.

Read | The social psychology that Manchester United have missed, and must reclaim, since Sir Alex Ferguson’s departure

Their league performance was far from perfect, however. A sixth-place finish was a long way off Mourinho’s prediction of potentially challenging for the title, but the Europa League afforded United qualification for the Champions League nonetheless. It was a season of transition for both Mourinho and United, but in his second season, the season he is famed for delivering in, he was expected to go all out for the title.

In the lead-up to the 2017/18 campaign, Mourinho brought in Nemanja Matić from Chelsea and Romelu Lukaku from Everton for a total of £115m to boost the ambitions of United, who looked to set for a fight with local rivals Manchester City for the Premier League title.

This battle would also hold some personal gravity for Mourinho, as managing the Citizens was his most famous opponent and philosophical antithesis, Pep Guardiola. The two hold such contrasting methods and ideas on how football should be played that their personal competition is the most fascinating in the modern era.

Alas, the anticipation ended as the season kicked off and United raced into an early lead with a peculiar run of 4-0 victories against Swansea, West Ham and Everton. It seemed that Mourinho had struck upon a winning formula that had defensive solidity and offensive firepower, which could bulldoze its way to the title – but Guardiola had an equally impressive line-up that had started in the same vein as United. Five games gone, both had won four and drawn one.

Three games and three wins later, both teams sat with the same record, only goal difference splitting them at the top. However, United slipped up, first drawing away at Liverpool and then experiencing a shock 2-1 loss to relegation candidates Huddersfield. Another loss to Chelsea the game after opened up a seven-point gap between United and City, who were in pole position and on a relentless winning streak.

Attempts to salvage this blip in form with a four-game winning streak were unsuccessful as City kept on winning and, when the two finally met at Old Trafford, any hopes of catching the Blues relied on a masterclass by Mourinho to topple their seemingly invincible neighbours. It was a challenge he simply couldn’t muster as City left with a 2-1 victory and the title firmly within their clutches.

Three draws on the bounce in December allowed City to pull away even further into a virtually unassailable lead. Although United showed defiance in April to come back from a 2-0 deficit against City at the Etihad and prevent them from winning the title against them, the Red Devils were ultimately left with egg on faces, a 1-0 loss against hapless West Brom gifting their rivals the Premier League.

In other competitions, United were disappointing. They were knocked out of the League Cup in the quarter-finals by Championship side Bristol City; they were poor against Sevilla in the Champions League Round of 16; and were lacklustre against Chelsea in the FA Cup final, Eden Hazard’s penalty sealing a trophyless season for the Red Devils.

While there was talk of the quadruple in the blue half of Manchester, you couldn’t help but feel that this United side could have done so much more to press City for the title and add at least one cup trophy to the cabinet.

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Mourinho was criticised by the media for a negative approach to games in which he could have let his wealth of attacking options off the leash, and whilst we know that this pragmatism is part of his nature, we also understand that this is only justified by consistent and worthwhile results. Mourinho had done this throughout his career but now, as times changed, the ways of the Special One were becoming harder to accept. Worryingly, he would need his third season to redeem himself – and history shows that third time lucky doesn’t bode well for Mourinho.

And so we arrive at the present. The reasons for Mourinho’s dismissal from United are strikingly similar to that of his demise at Chelsea, and the circumstances eerily linked: a lack of investment from the board and discord between the players leading to a sacking in mid-December. Anyone else feel a sense of déjà vu?

Not content with the extortionate spending spree that has set Ed Woodward’s budget back by at least £350m, Mourinho wrote up a list of players, mainly defenders, he hoped to sign for the upcoming season. When he was told ‘no’ by the board and only given Shakhtar Donetsk midfielder Fred for £52m, he threw his toys out of the pram and whined about it on the club’s pre-season tour of the US, as well as also complaining about French winger Anthony Martial being with his newborn son rather than thousands of miles away at the United camp.

Meanwhile, the man tipped by many to take the reins at Old Trafford in the summer, Mauricio Pochettino, was tight-lipped about the fact that the Tottentham board had signed nobody in the window,

Despite this, Mourinho was still demanding respect by throwing hollow stats that he thought could exempt him from criticism, yet this loss was just a week after the Red Devil’s were stunned by the Seagulls as Brighton outplayed a turgid United at home, winning 3-2. Then, in September, a day after United were dumped out of the League Cup by Derby, Sky Sports released footage of a prickly confrontation between Mourinho and star man Pogba.

This 30-second clip exploded beyond proportion but the media feasted on the opportunity of a manager-player feud, especially one of this magnitude. Soon, everyone was picking sides. Fuel was added to the fire when Pogba was subbed off after 70 minutes in a 3-1 defeat to West Ham at the London Stadium, a result that confirmed that it had been United’s worst start to a season in almost three decades.

Mourinho’s time at the helm was now a ticking timebomb. A humbling defeat to City, not laying a glove on Juventus, an unconvincing draw against Southampton, scraping a victory against Juve away that Mourinho lapped up as if to suggest it was his magnum opus, and a tiresome loss against Valencia tightened the net. Finally, after a media storm that had ensued for four months, United were soundly beaten by Liverpool after another turgid performance. Once again, Mourinho had come to the endgame. He left Carrington in the hands of Ole Gunnar Solskjaer and the team that had stuttered and stalled under his jurisdiction roared into life once again.

At Chelsea, there was remorse and regret towards José’s unruly departure, yet as he left United, there was a sense of relief that the club could move on from his era. Once the most sought-after manager in European football, Mourinho was left out in the cold.

In a London apartment, as cabs sail by like lone boats in an ocean, Mourinho will be planning his next move. As a coach, he has always been a methodical tactician, right from his days at Barcelona handing Sir Bobby Robson large dossiers of analysis to help his preparation for an upcoming game.

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He treats football as if it were a chess match, like many great pragmatists treat life. Everything we do has a consequence, and to succeed, we have to be multiple moves ahead. Niccolò Machiavelli would have used this approach to determine what one must do to ensure victory over their competition.

Yet Mourinho’s next move is uncertain. His legacy is beginning to unravel as the images of him lifting trophies as an annual habit are overshadowed by him scowling on the touchline at the end of a 1-1 draw with a mid-table team. If Mourinho looks at a football match like a chess match, we can infer the roots of his demise through a similar cause-effect logic.

The most crucial and reoccurring factor in Mourinho’s career for the six years or so is that at the end of his tenure at Real Madrid, Chelsea and Manchester United, he had seemed to have lost the dressing room, yet the circumstances of each collapse are all relatively ambiguous because clubs don’t tend to air out their dirty laundry.

From what we know happened in Madrid, the feud between Mourinho and Casillas had a major impact on the relationship between the manager and his team. Excluding such a beloved and influential figure on inconclusive evidence was a risky move from Mourinho.

At Chelsea, everything was rosy for two years and Mourinho got the Blues back to being the best team in England. However, events in the summer and in the first game against Swansea were pivotal. The transfer business conducted was meagre for a club with Champions League ambitions and left the Blues thin and without the necessary competition to incentivise glory. Mourinho had the right, I believe, to feel deserving of more personnel, but that would’ve excused missing out the title perhaps, not becoming relegation candidates by December.

The scandal involving Eva Carneiro tarnished Mourinho’s reputation, but did the players turn on him due to that incident or did more occur behind the scenes that resulted in the corrosive atmosphere that was created around the club in such a short space of time? Something substantial must have happened for the players to stop playing for the manager in one summer. It’s unclear and one can only hypothesise.

For me, it’s as simple as time catching up with the Portuguese. By his third season in charge at Old Trafford, he had become more pragmatic than ever, his style of play unashamedly defensive and cautious. Meanwhile, he wasn’t afraid to publicly call out his own players to – often unfairly – critique their performances or conduct. Luke Shaw, Anthony Martial, Marcus Rashford and others were criticised in Mourinho’s ever-eventful press conferences.

Mourinho hasn’t moved on with the changes occurring in the footballing landscape, not least in a game where players respond better to an arm around the shoulder than a cool ticking off. It seems that in his quest to win at all costs, he has failed to realise that his methods don’t work like they used to. Even Machiavelli was ousted from the Florentine Republic eventually.

There’s no question that Mourinho has a unique perspective and incredible experience in the beautiful game but the way in which he conveys this has been his downfall. His belief is to win at all costs, but to return to his peak, he may have to adapt that philosophy.

By Callum Patrick