There were two ways the message could have travelled from Porto’Ercole: to the left, through Orbetello and onwards to Florence, or to the right, eastward and straight to Rome. Naturally, it went to the right. The message was sent to Rome.

The July heat must have hastened the post. Summer in Italy is a dry affair, makes the sweat stick your shirt to your skin. The narrow, winding streets of Rome were baking in the compact sun; the beggars slept in the shade, the shepherds herded their flocks through into the fields, the grocers fanned at their produce, willing it not to wilt too quickly. The bells of the sheep and the church rang together. Everything swelled in the lazy, languorous heat, the dust, the clouds passing overhead.

The messenger was sent up a long and winding hill, offering a magnificent view of the city below, stretching into the distance as it multiplied and divided, coalescing together quickly after the sacking almost a century before. As he crossed the courtyard to the Quirinal Palace, stone eagles, dragons, the heraldic symbols of Pope Paul V, watched over him. He was lead into the dim innards, down lush halls and past glowing candles, until he came into a room, humming with chatter, large and vaulted.

He knelt before the slippered feet, kissed the holy stitching, and did not dare look into the man’s eyes as he relayed the message: Michelangelo Merisi da Caravaggio was dead.


When one thinks of Caravaggio, some of his more famous masterpieces come to mind:

Today, Caravaggio is known far and wide for being a master of the Baroque style; once called the ‘most famous painter in Rome’, his use of tenebrism (also known as chiascuoro, an oil painting technique contrasting light and dark) and his scandalous—often violent—but realistic depictions of religious scenes earned him no lack of fame and commissions in Rome. His depictions of religious scenes challenged the classic notion of how the audience thought they should be portrayed; instead of strewing them in halos and filing the canvas with wispy clouds and baby-faced cherubs, Caravaggio puts his subjects in undramatic, human settings—stables and dinner tables—and where previously moments of spiritual epiphany were heralded by flocks of angels and trumpets, he portrays these same moments as internal, something that has already happened to his subjects. In one instance, an official questioned him why his painting Conversion on the Way to Damascus featured a horse more prominently than St. Paul, the subject. He asked the painter “Is the horse God?”, and Caravaggio replied: “No! But he stands in God’s Light,” which, in a way, is a nice summation of the painter himself; always the bridesmaid, never the bride.

Although this writing is not necessarily a coverage of his art, but rather his life, Caravaggio was reflected often in his work, whether by painting himself into it or in the scenes he chose to depict. His life was just as much fraught with success as it was with failure; he was a complicated figure, who used prostitutes to stand in for the Virgin Mary, often cavorting with them himself, and who, despite or perhaps because of his wealthy patronage, was hedonistic in his pursuit of earthly pleasures, as well as its vices.

Despite his fame and fortune, Caravaggio was notoriously explosive, getting into fights and brawls so often that he became known for it, this in a time where men in Rome did little else but. Ultimately, and at the height of his career, he got into one argument too many, and what either began as a fight over gambling bets, a tennis game, or something more (which I’ll address later), Caravaggio attacked and killed a man named Ranuccio Tomassoni, and, now on the run, he fled to Naples, looked after by the watchful eye of the Famiglia Colonna.



The Colonna palace was built at the bottom of Quirinal Hill, with the family always looking upwards towards the papacy. The Colonnas, on occasion, managed to fill the seat with members of their family, relegated by both blood and marriage. They were a strong presence throughout Italy, claiming to be descended from Aenas, the founder of Italy, and though their main palace was in Rome, the family also occupied land in Lombard, near Milan, in the small town of Caravaggio. It was there that a child was born to the steward of Costanza Colonna, a boy named for the feast day he was born on: Michelangelo.

In many ways, Michelangelo Merisi da Caravaggio was as much a fashion and tool of the Colonna’s power as their own children were, and throughout his life the family showed him patronage and loyalty like no other. His initial fame was due, in part, to their dedication, for after he arrived from Milan he was sent to live with the Perettis, who had close familial ties with the Colonnas; when one of the Peretti women retired, she took her steward—as well as the steward’s roommate, a talented painter—with her, to the palace on Quirinal Hill, where Caravaggio’s career in Rome most likely began, and, ultimately, where it ended.

The palazzo Colonna was built near the site where it is said that Nero watched Rome burn. The tradition of being in view of but untouched by destruction remained in the land; during the Sack of Rome by Charles V in 1527, their palace was left untouched while the rest of the city burned, becoming a safe haven for thousands of citizens, average and venerated alike.

It became so again on or around the night of 28 May 1606. That day had been the anniversary of the Pope’s coronation, and the city had been caught in festivity. It was also on this day that Caravaggio and a group of friends had passed through the neighborhood dominated by the Tomassoni family.

Relations were poor between Ranuccio and the painter; they had a history of fighting, taunting, and arrogant pursuits to humiliate the other. The event which would change Caravaggio’s life had been a long time coming, built upon frequent quarrels and intense antagonism, as well as the painter’s own rumbustious nature. There was an argument between the two, and though the subject is contested, the result was not: a swordfight erupted, and the wounded Caravaggio parried with a strike to Tomassoni’s leg or thigh, though as the man fell the blade caught him in the stomach, fatally wounding him.

The cause for the fight is not entirely known. Tomassoni’s death is, in some ways, just as mysterious as that of the man who killed him. It could have been over a bet on a tennis game, or an unpaid debt owed by Caravaggio; it has also been theorized that his wounds in October 1605, which Caravaggio claimed had been a self-inflicted accident, had in fact been the result of an encounter with Tomassoni, whom Caravaggio had been forbidden to fight. The duel may even have begun over the honor of Tomassoni’s wife, Lavinia, who remarried within months of Tomassoni’s death (although the reasoning would have been appropriate; a woman at child-bearing age with little financial independence must look elsewhere for her own wellbeing).

As far as matters of blood had been concerned, the promised debt had been fulfilled. When men fight, violence is, by their nature, imbued into the matter at hand. The law, however, is more concerned with the conclusion than the justification.

The news broke wildly about not only the city but the rest of Italy; there is not quite a modern or contemporary artistic figure on the same level of celebrity as Caravaggio was at the time, but it would be as sensational, perhaps more so, as the reaction to OJ Simpson being arrested for murder.

Where can one go after fleeing the scene of a crime they were responsible for? More particularly, where does a celebrity go? For Caravaggio, he went to where his career began: to the bottom of Quirinal Hill, right under the Pope’s nose, in the Palazzo Colonna.



Caravaggio did not stay in Naples long, perhaps about a year, before he left, heading directly south, straight through Palermo and Sicily.

The island of Malta has long been a strategic buffer which separates the Mediterranean and North Africa from western Europe, a brief stop between Tunis and Athens, yet also a stone’s throw from Sicily. In Caravaggio’s time, it was known as a Christian stronghold which kept the Ottoman Turks at bay, and was home to the Knights of the Order of St John, who had relocated there in 1530 after their exile from Rhodes.

This last chapter of Caravaggio’s life was just as—if not more—mysterious than the rest of it had been. He had arrived either for protection or for glory; the Knights had long been the standard of Christian chivalry, and for reasons not quite clear, he wanted to join them.

Malta was a painter’s dream; the blue, clear water,  the churches and buildings which rose, tiered, from the sea, half-shadowed, half glowing in the sun, perfect for an artist who specialized in both. The fortress of Valletta, built by the Order and flanked on either side by two harbors, had been constructed in only 15 years, and was finished in 1581, two decades before Caravaggio arrived, and the same year that a revolt was staged against the Grand Master of the Order, predecessor to Alof de Wignacourt, for his attempt to rid Valletta of ‘loose and disorderly’ women.

Wignacourt had initially arrived in Malta from France after the Great Siege of 1565, in which the Ottoman Empire had tried to overtake the island. He rose to become Grand Master in 1601 on his popular pledge that he would return the Order to its previous shining status (at the time it was riddled with violence, post-Crusade Inquisitional boredom, and said ‘loose and disorderly’ women).

Like Caravaggio, Wignacourt had fallen under the powerful spell of the Colonna family, having safeguarded the imprisonment of Fabrizio Colonna, wayward son of Costanza, who had befriended and supported Caravaggio early on in his career. (I may have to add a later appendage on the Colonna family itself – their history, like many prominent Italian legacies, is far reaching and fascinating.)

The Knights of Malta had seen better days by the time Caravaggio had come to them, him being interested in both their power and relations to the Colonna family. Almost immediately upon his ship docking at the island—and he had almost certainly been expected—he was welcomed into the house of one of the knights, Fra Giacomo Marchese, and had his every need attended to by servant and slave alike.

Alof de Wignacourt, by Caravaggio

It is no wonder that such a cushy position and renowned fame led the painter to meet with the Grand Master Wignacourt, whose portrait he eventually painted. His work was so well-received by Wignacourt that it is said to have earned him the Cross of Malta, and certainly the Grant Master’s own campaign to have the painter inducted into the Order, which had a particularly strenuous application process, requiring, among other qualifications, a hefty sum of money known as a passaggio, two hundred years of nobility in all four genealogical lines, and no record of marriage or murder (and, of course, Caravaggio met only one half of the demand). The campaign was helped along by a letter from Pope Paul V, the very man Caravaggio had petitioned for a pardon, which requested that knights be valued on merit or virtue rather than ancestry. For the son of a steward, this was welcome news.

Wignacourt petitioned tirelessly for Caravaggio’s acceptance into the order, writing letters to the Holy See and its Ambassador, and even the Pope himself, to bestow the painter with the habit of ‘Magistral Knight’ (the Order being, of course, holy, and therefore required adherence to religious custom). The Pope granted Wignacourt’s request, even in spite of the killing of Ranuccio Tomassoni; this act perhaps began to convince Caravaggio that a pardon was imminently within his future, and he might be able to return to Rome without fear of the banda capitale, the death sentence placed on his head to be collected by anyone, at any time.

The goodwill and glowing reviews of Caravaggio, despite the artwork he created while in the Order, did not remain eternal. Perhaps due to his tempestuous nature, his egotistic fancying of himself an aristocrat, or his otherwise view of himself as being under the full protection of Wignacourt and the Colonnas, but certainly due to his tendency towards violence and an argument with another knight, he was put into prison on the island at Castel Sant’Angelo. He quickly escaped, vaulting over the prison walls one night and escaping to Syracuse.

Not only had he broken a cardinal rule of the Order by fighting with a fellow brother, but he had also violated Statute 13, which forbade members from leaving the island without permission. Due to this, and his failure to appear at the tribunal, Carvaggio was stripped of his knighthood, and, proving that history is not without a sense of dramatic irony, the dethronement ceremony took place before Beheading of St John, finished by the painter just four months earlier.



On a day quite similar to the own which carried news of his death a year later, Caravaggio returned to Naples, sometime in the summer of 1609.

He was hopeful for a papal pardon, having been in self-imposed exile from Rome for nearly five years. Arriving in Chiaia, west of Naples, he rested at the Palazzo Cellamare, a short distance from the Colonna palace; he was most likely searching for amnesty from the family yet again, as he had been hosted by his old patroness, Costanza Colonna, who was visiting the area.

As ever, his stay was brief, for wherever Caravaggio walked, violence often followed. Shortly after he arrived, while drinking at what is called the most famous tavern in Naples, the Osteria del Cerriglio, he was attacked so brutally that for a short time there was news circulating that he had been killed, or mortally wounded. Subsequently, his convalescence kept him for some months were he was, yet he set out for Rome sometime that autumn.

During this time, his work began to reflect the violence that had beset his life; he painted some of his bloodier works, assassinated figures like The Crucifixion of St Andrew, Salome with the Head of St John the Baptist, as well as David with the Head of Goliath. In a supposed act of contrition, the head that David holds – that of the giant felled by pride – is Caravaggio’s own. It is also interesting to note that what is supposedly Caravaggio’s last work, The Martyrdom of Saint Ursula, is of a penitent figure in the moment of assassination, grey and bloodless hands at the arrow that pierces her breast as she stares down at the fact of her own demise; on the far right, the artist himself witnesses her death.


These final works were supposedly meant as gifts to tide over Cardinal Scipione Borghese, a notorious art lover, and a man capable of issuing pardons. Caravaggio had left some of his paintings at the Palazzo Cellamare with Costanza Colonna, but others he brought with him onto a felucca, a sailing boat, as he headed back towards Rome. Intending a triumphant return and backed by powerful families, the Colonnas among them, who had led a revived demand for his work, he also traveled under a guarantee of safe conduct from Cardinal Ferdinando Gonzaga. This did not prevent him, however, from being placed under arrest by the captain of the felucca when the ship docked at the small port of Palo, where Caravaggio had presumably intended to disembark.

The ship continued on to Port’Ercole. Desperate to escape, Caravaggio bought his freedom, though this left him destitute and in a remote, isolated terrain, infested with dregs of outlaws and mosquitos. Although he had been eager to leave his imprisonment on the ship, he had left his work on board, and upon returning to port he discovered that the ship had continued on without him.

Having no other option but to walk the more than one hundred kilometers to Rome, he began his journey, but ultimately left it unfinished. After a brief admittance to San Sebastiano, a confraternity dedicated to the ill and travelling, Michelangelo Merisi da Carvaggio died on 18 July, at or around the age of 36.

What ultimately killed him is unknown. His still healing wounds might have become infected, or he had possibly contracted malaria, or he might have succumbed to any number of diseases, beset by a persistent fever or a short but intense illness. There also remains the possibility that he was assassinated, potentially by the Order of St John, whose laws and values he had desecrated, and after so much of their investment—personally so on behalf of Wignacourt—had been placed in admitting him in the first place.

The Wignacourt aspect is particularly interesting, simply because the man put himself and his reputation on the line in fighting on behalf of the painter. His incessant letters to the Holy See had their viability and credibility laying wholly on his achievements and his dedication in his post at the Grand Master; to have his goodwill not only rejected by Caravaggio, but also to be humiliated and have an institution he held dearly and close to himself disrespected so flagrantly—an institution that he himself was in charge of—must have stung. Although the painter managed to elude any Maltese punishment, it is believable enough that perhaps the brawl he was involved in at the tavern Cerriglio was an extension of the Order’s justice, a banda capitale of sorts, ordered by the man who had gambled on benefiting from the presence of a volatile celebrity, and had lost.

Violence followed Caravaggio through his entire life. They were no strangers to each other, constant bedfellows, and it would not be surprising if a violent life met a violent end. On the other hand, and at the heart of this mystery, it is also known that Caravaggio was not in good health, partly due to his injuries, and it is not a far reach to presume that he was felled not by the sword itself but the damage it has inflicted.

Perhaps it was the two, together. The Order had tracked him down, persuaded the captain of the felucca to imprison him so that he could not possibly escape, or had followed Caravaggio after their failed attempt in Naples. Already seeing that he was not only wounded, but feverish—as good a death sentence as any, especially so far from any good doctor and their medicine—the brothers find the fugitive at San Sebastiano and, with or without notice from the friars there, see their job finished. They smother the painter as he sleeps, or as he tosses in a feverish haze, or they stab him in the heart and he spends his last moment in imitation of St Ursula, glancing down at the fatal blow, realizing he has met his end and there is nothing he can do about it but bear witness.

Whatever the cause of his demise, to be sure it was slow and torturous. His security for his pardon, so close at hand and no more than one hundred kilometers away, had floated away from him, stowed somewhere in the depths of a ship that had also been his prison, and all of his money and clothes had gone with it. The cosmopolitan character, once so fêted and celebrated, who had reached the highest points of his career in a city that loved him and now called on him once more to raise him upwards again, had been marooned on a frontier known for little more than its existence as a fishing village. He would not die as an old man in his bed, surrounded by wealth and symbols of his own prestige—something which had eluded him his entire life, no matter how much he might have sought it. He would die slowly, an unknown figure on a forgotten island, no less than a hundred kilometers away from his own salvation, caught in fevered hallucinations of grandeur.


Who, then, was left to cry for Caravaggio?

Who mourned his death? Perhaps the Colonnas, there in their palazzo on Quirinal Hill, distraught over not only their prized artist, but the man who they had raised and protected since his birth. Perhaps when Costanza took his final paintings from her home in Naples, she inevitably thought of him. Perhaps all of Rome wept, except the one dark house of the Tomasonnis, who had not forgotten their own son.

Upon the hill, at its peak, it is unknown how the Pope received the news, or his nephew, the Cardinal Borghese, who had been promised so many great works in exchange for safe passage.

The bishop Deodato Gentile had been sent to Naples to retrieve the master’s last paintings from Costanza Colonna, and to search for those left on the felucca after it departed Port’Ercole. He soon found that the paintings were being guarded by Fra Vicenzo Carafa, a member of the Order of St. John, who claimed that the paintings now belonged to the brotherhood, although eventually, after much bureaucratic intervention, the works were returned to Cardinal Borghese.

It is not known exactly where Caravaggio was buried, although recent findings have indicated that his remains may have been found. In lieu of a resting place, Marzio Milesi composed an epitaph as a final memorial to his friend, a man talented and complicated, fraught with a mercurial and temperamental nature, but no less brilliant for his mastery of work. It reads as follows:

“Michelangelo Merisi, son of Fermo di Caravaggio – in painting not equal to a painter, but to Nature itself – died in Port’ Ercole – betaking himself hither from Naples – returning to Rome – 15th calend of August – In the year of our Lord 1610 – He lived thirty-six years nine months and twenty days – Marzio Milesi, Jurisconsult – Dedicated this to a friend of extraordinary genius.”

Further Reading

Isman, Fabio. “What a Century: When Caravaggio Arrived in Rome.” Caravaggio’s Rome 1600-1630: Essays. Skira. 2012.

Langdon, Helen. Caravaggio: A Life. Random House. 1998.

Sammut, E. (1949). “Caravaggio in Malta” (PDF). Scientia15 (2): 78–89

More on the Colonna Family.