The Portrait of a Young Man in a Red Cap was painted by Jacopo Carucci (also known as Pontormo). It’s dated at 1529 and said to depict a young Florentine aristocrat named Carlo Neroni.

But I believe it to be someone else: Lorenzino de’ Medici, the man who claimed he assassinated his ‘friend’ and distant cousin Alessandro de’ Medici, Duke of Florence, on the eve of the Epiphany, January 6, 1537.

A few days later Lorenzino, who was a gifted writer and dramatist, declared openly the reason he murdered the duke was political, to free Florence from a tyrant and Medici rule and preserve the Republic of Florence. He compared his actions to those of the ancient Roman politician Brutus, famous as one of the assassins of Julius Caesar.

In my previous post about Giorgio Vasari’s painting of the marriage between Henry, Duke of Orleans, and Catherine de’ Medici, I explained how the head placed on the shoulder of Pope Clement VII represented three people: Alessandro de’ Medici (Duke of Florence), Galeazzo Maria Sforza (Duke of Milan), and one of the latter’s assassins, Giovanni Andrea Lampugnani. I made no mention of the name of Galeazzo’s assassin. But he is placed elsewhere in the picture, his head also on a shoulder, that of the French king Francis I (see image below).

Unfortunately, I haven’t yet been able to source a higher resolution of this painting, so the important detail embedded in this section of the picture is difficult to pick out. Nevertheless, this group of three men provides some clues to be able to identify Lorenzino as the head in the middle.

An episode in Lorenzino’s early life confirms his connection to the cardinal featured on the right. He is Ippolito de’ Medici, an illegitimate son of Giuliano di Lorenzo de’ Medici and therefore a distant cousin of Lorenzino. As can be seen by his attire he was a cardinal, though never an ordained priest. He was made Cardinal by another illegitimate cousin, Pope Clement VII, on January 10 1523. On the same day he was also appointed as Archbishop of the Avignon diocese in France, which explains one of the reasons Vasari has placed him on the French side of the marriage scene.

Another reason is that while he was serving in Rome he pleaded for Lorenzino who in 1538 upset Pope Clement VII by mutilating the heads of some of the statues on the Arch of Constantine. The outcome was that Lorenzino was expelled from Rome, a lighter punishment than the one the Pope had first threatened – execution. And so from this we have another ‘head’ connection.

Ippolito and Lorenzino also shared an interest in deposing Alessandro de’ Medici from his position as Governor and Duke of Florence. However, Ippolito wanted the title for himself and lobbied Clement VII for the position, but the Pope’s choice was his own son. Ippolito never tired of conspiring against Alessandro and seemingly paid the the price for his efforts when he became ill on a journey and died a few days later after claiming he had been poisoned on the orders of the Florentine duke. He was just 24 years old.

Vasari’s image of Cardinal Ippolito is probably based on his portrait painted by Titian in 1546.

It’s hardly apparent, but as in the Pontormo portrait, Lorenzino is wearing a red cap. Neither is his head completely visible. It is eclipsed by the head of Francis I.

Here, Vasari, has referenced the mythological “cap of invisibility” also known as the “cap of Hades” that turns the wearer invisible, a cunning devise to conceal their true nature – as in the perceived ‘friendship’ offered by the assassin Lorenzino to Ippolito.

Hades helmet of invisibility was also shared with the messenger god Hermes who wore the cap in his battle with Hippolytus the giant. And so this makes the connection with the name of Cardinal Ippolito, who wears a red biretta in the painting.

The cap or helmet of invisibility also features in Botticelli’s Primavera painting and in a section referencing Hades (god of the dead and the underworld) and the watchdog Cerebus. The symbolism also points to the Dominican Order of Preachers sometimes known as the “Hounds of the Lord” or “God’s Dogs”.

In the clip below (left) is the ‘shade’ of an ‘invisible’ monk’s cowl and hood; and (right) the outline of a hound’s head.

• More on this in a future post.