Everybody loves the anti-hero. Dark and flawed, with both eyes on the main prize – the success of themselves – they have a history in fiction that extends from Don Quixote to Deadpool. They exist in real-life too and Milan has given rise to two great anti-heroes. One was born there. The other was manager at Inter. Both were superstars during career defining six-year periods of greatest success. Both deployed working methods that defied the prevailing orthodox of their day and horrified their critics. Both then fell like supernovas, burnt out and doomed.

Caravaggio and Jose Mourinho are the Deadpool of their days. They are the two anti-heroes of Milan, 400 years apart.

It was half time at Camp Nou, Wednesday 28 April 2010 and Jose Mourinho stood on the verge of reaching the Champions League final. All he needed to do was organise and inspire his 10-man Inter to hold out for a further 45 minutes and deny the club that had rejected him as manager – Barcelona.

Two years earlier, Mourinho had thought himself favourite to succeed Frank Rijkaard as Barcelona manager only for Johan Cruyff to recommend Pep Guardiola instead. Mourinho never forgave Guardiola and Barcelona for the rejection. He was translator at Barcelona in the mid-1990s, 20 years after Rinus Michels brought Johan Cruyff from Ajax and developed Barcelona’s own version of Total Football.  

Louis Van Gaal, Ronald Koeman, Luis Enrique, Laurent Blanc, Phillip Cocu, Frank De Boer and Guardiola himself were also at Barcelona in the mid-1990s. All went out into the world and spread the good word of Barcelona-style possession-based football. Except Mourinho. Like Caravaggio in the late 16th century, his career was kick-started and promoted by a respected figure – Sir Bobby Robson. Robson hired Mourinho as translator at FC Porto then took him to Barcelona.

As he was not a player Mourinho was different from his peers at Barcelona. In his formative years as a manager he did not adopt the attacking, possession-based game imported from Ajax. Then, in 2008 after being rejected for Guardiola, Mourinho developed a defensive anti-possession style of play for Inter. It was an anti-Barcelona style that would ultimately enable the 10-men of Inter to reach the Champions League final at the expense of Barcelona, developed in defiance of Barcelona, Rinus Michels and Johan Cruyff.

Over 400 years earlier, a Milanese artist defied Raphael and Michelangelo – the Michels and Cruyff of their day – and painted in a radically new style. Born in Milan, Michelangelo Merisi took the name of the town he grew up in, the name by which he’s been known forever since – Caravaggio.

Caravaggio moved to Rome in the 1590’s and attracted his patron, Cardinal Francesco Del Monte with his painting, The Cardsharps. Close study of the picture hints at the unconventional methods Caravaggio employed to execute the painting and explains why Del Monte would have been so curious to work with its creator. The Cardsharps is at once perfectly natural looking and realistic – check out the feather in the cap of the cheat at front right for realism - but you may then wonder, has the same model has been used for both the cheat and the youth being cheated? Why is the furtive glance of the older cheat with three fingers raised at rear missing the cards? And aren’t the figures crowded together in a small space? Del Monte recognised these details as evidence of Caravaggio using optical instruments, such as a convex mirror or Camera Obscura to reflect or project images straight onto the canvas.

As such, The Cardsharps would not have been painted by the conventional method of having three models pose round the table and Caravaggio “eyeballing” the image from life, onto the canvas. Rather, the work would have been painted as a collage, where the figures were posed, projected and painted separately onto the canvas, one at a time. Connoisseur of the arts and science, Del Monte saw the meeting of art and science in The Cardsharps. He saw the great potential in Caravaggio and became his patron.

In the six years between 1600 and 1606 Caravaggio created art that made him famous forever. He painted directly from posed models in a revolutionary chiaroscuro style and invented Hollywood lighting still hundreds of years in the future. He took models drawn from his real life cohort on the street – bravi, labourers and prostitutes – and painted them as saints and the populace loved him for it. In the 1601 Supper at Emmaus, amidst the high drama of gripping the chair, the meticulous white tablecloth and the perilously perched basket of fruit, Caravaggio painted the resurrected Christ revealing himself to two workmen in a dark corner of a Roman tavern.

The critics were horrified by the plebian naturalism in Caravaggio’s art and scandalized by his unconventional working method of painting from life, directly onto the canvas. The criticism enraged Caravaggio. During the six years of his imperial Roman period 1600 to 1606, when he was “The Most Famous Painter in Rome,” he turned increasingly violent. Eventually, in 1606 Caravaggio murdered Ranuccio Tomassoni. He fled Rome and lived out the remainder of his life in exile, in Naples, Malta and Sicily.

Caravaggio painted many great pictures after 1606 but something in his art died with Ranuccio Tomassoni. He dropped his predominant concern of painting a likeness to life for a looser, much darker vision. If you compare the 1606 Supper at Emmaus – now in Milan – with Caravaggio’s previous version of the same subject, painted in Rome five years previously, you can see the change that has now overcome Caravaggio’s art. No more the drama of elbows and baskets of fruit breaking the picture plane. The vibrant Christ of the Roman years has been replaced by a weary man of middle age. Someone has turned out the lights. Had Caravaggio been pardoned for Ranuccio Tomassoni’s murder and returned to Rome, his milieu and his optics, likely he’d have returned to the great Roman style that made him famous. However as a man on the run, creating bleak, spare art in record time for his Southern patrons he was the Titanic of the painting world on his long fall to the bottom of the sea.

Though it is still early days at Manchester United it would seem Jose Mourinho’s star is also in its descent. In March 2004 he dashed up the Old Trafford touchline on his way to his first Champions League triumph with Porto. So began his own imperial six-year period of seven major titles in England and Italy, bookended by his second Champions League title with Inter in 2010. He has been less successful since.

Just as the public loved Caravaggio, Mourinho was loved at Chelsea for winning their first league title in 50 years and adored at Inter for delivering the first European Cup since the era of Grande Inter. His critics, however - like Caravaggio’s before him - were appalled by the methods used to deliver that success. Mourinho tightened to a defensively solid 4-3-3 in his first period with Chelsea and was criticized for winning boring. He avenged his rejection at Barcelona by sending out his 10-man Inter team for the second half at Camp Nou in 2010 and won through to the Champions League final “devoid of joy,” and with only 19% possession. At Real Madrid his full anti-Barcelona philosophy was published in a notorious biography. The world learnt that, “Whoever renounces possession reduces the possibility of making mistakes,” and the press was scandalized.

Caravaggio may have changed the direction of western painting and invented Hollywood lighting but he was forgotten for hundreds of years after his death. When resurrected in the 1950’s the genius of his art – with its hyperrealism, heightened drama and casual violence – was to transcend time and appear forever modern. It enraptured a modern audience anew.

Will history be so kind to Milan’s other anti-hero, Jose Mourinho?  

David is author of The Lost Caravaggio