From the December 2025 issue of Apollo. Preview and subscribe here.

Alexander Noelle of the Cleveland Art Museum explains why Filippino Lippi excelled at the circular ‘tondo’ form of painting.

In 1488, Filippino Lippi, then in his early 30s and one of the most revered painters in Tuscany, was called away from his most prestigious commission to date – decorating the family chapel of the banker Filippo Strozzi in Florence – to relocate to Rome. This unusual request came about by two luminaries pulling rank. It was Lorenzo de’ Medici, de facto ruler of the Florentine republic, who plucked Filippino from his home city and packed him off down south. But he did so at the behest of the Neapolitan cardinal Oliviero Carafa, who wanted to commission a major cycle of frescoes for his own chapel in Rome, in the Dominican basilica Santa Maria sopra Minerva.

Filippino began work on the chapel that year – a project that would take him half a decade. But frescoes are best painted in warm conditions and, with time on his hands during the winter months, the artist took on another commission from Carafa: the exquisite tondo The Holy Family with Saint John the Baptist and Saint Margaret (c. 1488–93). A ‘tondo’ is a type of circular work of Renaissance art, and Filippino had tondi in his blood. He learned his craft from his father, the Dominican friar Filippo Lippi, and was later taught by Botticelli; both were noted for their skill in painting devotional works in a circular format. We take these works somewhat for granted now, but tondi were uniquely Florentine and uniquely challenging: it’s not easy to squeeze four or five people into a circle.

A few years before he began work on The Holy Family, Filippino completed a diptych of tondi depicting the Annunciation for the government of San Gimignano. Splitting one scene into two was groundbreaking in itself, but he also orchestrated a complicated series of perspectival coups that were unique to each tondo as well as harmonious across both. It was an ingenious approach to a traditional subject and, with The Holy Family, his most detailed tondo yet, he took his mastery to a new level. Monumental in scale and composition, it is only slightly smaller than the largest tondo he ever made: Virgin and Child with the Young Saint John the Baptist and Angels (c. 1483), the second-largest extant tondo produced in Renaissance Italy.

In The Holy Family, the Virgin dandles the Christ Child on her knee. To her left is Saint Margaret, who holds young John the Baptist as he grasps the arm of Christ. These characters constitute an overlapping, interconnected unit; meanwhile, Saint Joseph sits outside this group on the left of the painting. Partly obscured by the Virgin’s drapery, he seems to be divided from the others by an ancient column. Nonetheless he is a significant part of the composition. Joseph, like Mary, was mortal – the adoptive father of Christ. He indicates how we are meant to interact with this painting: serenely, in adoration and contemplation. Joseph draws you in to the composition. We look at him and he’s looking at them, but he’s also removed from them just like we are.

Equally inviting are the objects on the parapet, which seem close enough that we might almost reach out and touch them. They betray signs of Netherlandish influence: Filippino painstakingly captures the weave of the little reed basket and adds items such as the small ovular box and the reed cross on top. Devotional paintings from Northern Europe were full of such finely detailed still-life elements. Between the box and the basket lies a book, in which the text is worth noting: it is made up of recognisable characters but the words they form aren’t real, they just vaguely resemble words. The first word on the right-hand page, for example, almost resembles ‘Lumen’, a Latin word for ‘light’, but doesn’t quite get there. The Holy Family is the only known work by Filippino that does this: depictions of writing in all his other paintings are either clearly legible, if the work was large-scale, or totally illegible if the work was intended for private devotion.

The book, placed facing the Madonna as if she had just put it down to pick up her child, is one of several references to Filippino’s patron. A proud theologian, Carafa claimed Thomas Aquinas as not only his patron saint but also his ancestor, and an open book was one of the cardinal’s personal symbols. But the painting also hints at a more violent side of Carafa, who, alongside his ecclesiastical duties, served as admiral of the papal navy. The cardinal surely requested Saint Margaret’s presence in the painting: Margaret was believed to be from the coast of Asia Minor and it was this coast to which Carafa had laid siege in 1472, returning with Ottoman prisoners and spoils of war. On the capital of the column in the mid ground, the hunched figures holding shields – which closely resemble figures found in the Carafa family chapel – are thought to represent the prisoners he brought back.

The reliefs of arms and armour on the column capture Carafa’s military prowess and his erudition simultaneously. They refer to Ephesians, in which it is said that the faithful should wear the ‘armour of God’, complete with the ‘breastplate of righteousness’, the ‘shield of faith’, the ‘helmet of salvation’ and the ‘sword of the Spirit’. All are visible on the column, which has been carefully painted to look like a ruin, with pieces chipped off and vegetation growing on the capital. As in several works by artists including Botticelli, it implies Christ is the new order, rising from the ashes of the pagan world of old.

Filippino may well have based the column on a specific piece of ancient architecture he saw in Rome. Of course, Florence had its fair share of antiquities, but there were far more in the Eternal City and, in c. 1480, after a teenager accidentally fell into a grotto that contained the long-forgotten ruins of Emperor Nero’s Domus Aurea, Rome became a destination for antiquarians and artists keen to descend through holes in the ground to draw inspiration from the ancients. Filippino filled whole sketchbooks with records of architecture, sculpture and murals he discovered in Rome; he transformed one sketch of an ancient sculpture of Venus into an idealised female saint, which he used as a template for holy women in multiple paintings – including Saint Margaret in The Holy Family.

The years Filippino spent in Rome were the fulcrum of his career. Not only did he start incorporating decorative elements he’d seen in his studies of antiquity, but his conception of space also evolved. He began to pull the principal figures closer to the foreground, informed by his study of ancient reliefs such as those on sarcophagi. In The Holy Family it’s remarkable how he manages to balance the intricate, intimate still-life elements in the foreground with the monumental sacred vision behind them, filled out by hierarchical-scale figures – the Madonna is by far the largest character – and expanses of flowing drapery.

Fabric was central to the Florentine economy. Like Botticelli and Filippo Lippi before him, Filippino knew good silk and understood that painting it well created the impression of wealth and magnificence, an impression Carafa was keen to furnish. Lapis lazuli, which had to be imported from the Middle East, was far more expensive than gold; where normally this pigment was reserved for the Virgin’s mantle, there is lapis lazuli over everything in this painting, even on the roofs in the background and in the sky. The voluminous jewel-tone fabrics in The Holy Family cast their own deep shadows: sculptural and craggy, they are almost like mountains, giving heft and weight to the figures who wear them.

It is perhaps here that Filippino departs most from ancient tradition, in which fabric was depicted as skin-tight or designed to accentuate certain muscles or parts of the body. In The Holy Family we can’t get much of a sense of anyone’s physique except that of Christ, who is swaddled in a diaphanous veil. Filippino’s handling of Christ demonstrates his extraordinary delicacy, from the opalescent halo that glints like the skin of a soap bubble to the child’s translucent garment. Not only is the veil supremely well rendered, it also tells a story: see how it ascends from the half-open box on the parapet like a wisp of smoke, past the reed cross and up to encircle Christ. The Crucifixion, the Entombment and the Resurrection are there to see in this one vertical line, which, in a final masterstroke, continues upwards to seemingly become one with the Madonna’s own veil.

Also evident in the focal point of the painting is Filippino’s strength of line. Though influenced by Botticelli’s talent for graceful figures defined by clear outlines, Filippino took his command of line a step further to indicate space and collapse space at the same time. If we look closely at the way the Virgin’s hand reaches over John the Baptist’s shoulder, we see a very clearly defined border between her index finger and the Christ Child’s pinkie. But look even closer and it’s impossible to tell whether it’s hovering over his hand or actually touching it. In fact, no one in the painting is touching Christ directly; he is always mediated either by a veil or by an ambiguous space. The children’s faces overlap while not overlapping: the line that defines Christ’s cheek is the same one that defines John the Baptist’s little nose.

Filippino wasn’t the first artist to ever show children with overlapping faces, but his distinctive way with collapsing space was seized upon in Florence by Raphael and other major artists. Although the painting itself didn’t travel to Florence as far as we know, Filippino’s cartoons for it did, and this is how the motif gained currency. Upon his return to Florence after the Carafa commission, Filippino counted Leonardo da Vinci as a peer and took over three of his commissions in the city when Leonardo moved to Milan.

Now in the collection of the Cleveland Museum of Art, The Holy Family is generally thought to be the most important work by Filippino in a collection outside of Europe. The manner in which the painting came to Cleveland is rather more dramatic than most museum acquisitions. After spending most of its life in Carafa collections in Rome and Naples, it was acquired at the turn of the 20th century for Susan Cornelia Clarke, a Boston socialite and philanthropist who was second only to Isabella Stewart Gardner in the avidness of her collecting. Clarke was a major donor to the Museum of Fine Arts in Boston, where it was generally assumed that the painting would end up. Her children, however, had concerns about the conditions of the museum’s galleries. They tried to give it to Gardner, an avowed super-fan of Filippino Lippi. But she had already finalised the hang of her namesake museum and the tondo was too magnificent a painting simply to be slotted in; and so, tearfully, she declined. The dealer Joseph Duveen was interested for a time, furtively sending telegrams in code to his London office (codename of Bernard Berenson, agent and advisor to the firm: ‘Doris’), but ultimately Clarke’s heirs were so insistent that the painting remain on public display and in suitable conditions that the Cleveland Museum of Art emerged the surprise winner in 1929. The rest, as they say, is art history.

As told to Arjun Saijp.

Alexander Noelle is curator of European paintings and sculpture from 1500–1800 at the Cleveland Museum of Art.

‘Filippino Lippi and Rome’ is at the Cleveland Museum of Art until 22 February 2026.

From the December 2025 issue of Apollo. Preview and subscribe here.