An Eternal Dialogue: Holbein’s Portraits of the Thomases

Hanging side by side at Frick Madison, Holbein’s portraits of the rivaling Thomases from the Tudor dynasty confront each other once again.
An Eternal Dialogue: Holbein’s Portraits of the Thomases
Holbein’s portraits of the Thomases face-off at the Frick in New York City. Public Domain
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One of the most dynamic displays of portraiture can be found at The Frick Collection. Its face-off presentation of Hans Holbein’s portraits of Sir Thomas More and Thomas Cromwell spark an eternal dialogue, as these men were bitter rivals who each met a dramatic end in the Tudor court.

Normally, these paintings are arranged on either side of the Living Hall’s mantelpiece in the museum’s historic New York City mansion, which is how they were presented while the Frick family was in residence. This edifice has been closed, however, for an ambitious renovation and enhancement project, during which time the museum has taken up temporary residence at the modernist Breuer Building.

Currently called Frick Madison, this exhibition through March 3, 2024, allows visitors to see these Holbein portraits hung directly side by side, amplifying their unspoken debate.

A Meticulous Technician

Self-portrait of Hans Holbein the Younger,  circa 1542–1543. Pastel on paper. Uffizi Gallery, Florence, Italy. (Public Domain)
Self-portrait of Hans Holbein the Younger,  circa 1542–1543. Pastel on paper. Uffizi Gallery, Florence, Italy. Public Domain

Hans Holbein the Younger (1497/1498–1543) is considered one of the greatest portraitists of all time. In the National Gallery of Art’s catalog “German Paintings of the Fifteenth Through Seventeenth Centuries,” John Oliver Hand and Sally E. Mansfield write: “An assured, meticulous technician, Holbein’s insights into the character of his sitters are achieved, somewhat paradoxically, through his cool, emotional detachment and objective, astonishing realism.” In addition to his painterly genius, Holbein is lauded for his great skill and inventiveness in making prints, miniatures, and designing jewelry.

Born in Bavaria into a family of artists that included his father, brother, and uncle, it is likely that Holbein first received instruction from his father. By his late teenage years, he was working in the city of Basel, Switzerland, where he quickly received civic and private commissions. The artist traveled in the humanist circle of the eminent Northern Renaissance philosopher Desiderius Erasmus. It was Erasmus who introduced Holbein to the British intellectual and statesman Sir Thomas More.

In 1526, Holbein traveled to England and worked there for two years, staying with More, who became an important patron. In 1532, Holbein returned to England after four years back in Basel. It was during this second period that Holbein achieved his greatest success—becoming court painter for King Henry VIII. His portraits of the king and his family are emblematic of the Tudor era. Holbein died in London of the plague in 1543.

Sir Thomas More

A portrait of Sir Thomas More, 1527, by Hans Holbein the Younger. Oil on oak wood, 29 1/2 inches by 23 3/4 inches. The Frick Collection, New York. (Public Domain)
A portrait of Sir Thomas More, 1527, by Hans Holbein the Younger. Oil on oak wood, 29 1/2 inches by 23 3/4 inches. The Frick Collection, New York. Public Domain

Hans Holbein’s portrait of Sir Thomas More is one of the most beloved objects at the Frick and is considered a high point of the artist’s career. More was a lawyer, nobleman, humanist, and man of letters. His most famous work is “Utopia,” which is set on a fictional island and describes his ideal type of government. This book coined the word “utopia,” and its ideas have spread and influenced global thinkers throughout the centuries.

More was active in Henry VIII’s government, as well as being a close friend of the king. He served as Lord Chancellor from 1529 to 1532, succeeding the once all-powerful Cardinal Wolsey. Holbein’s portrait was painted before More ascended to this role, but it shows him wearing a gold chain pertaining to his status as a statesman. Scholars know that More owned a chain that he refused to take off, even during his later imprisonment. The chain in the portrait may have been gifted to him when he was made a knight or became a privy councillor. Art historians believe that its golden letters may stand for the motto “Souvent me souvient,” or “Think of me often.”

Much of this painting’s brilliance lies in the details. In addition to the chain, Holbein renders with virtuosity fabrics and textures, such as More’s red velvet sleeves and the fur trim of his coat. His face, framed by a striking black cap, shows a subtle stubble of beard. The background is an extraordinary green curtain bound with a rope, which casts a shadow on the curtain itself. More’s realistic hands draw the viewer’s attention to the ring on his left hand and the letter in his right. The inclusion of the letter has contributed to scholars’ belief that the purpose of the portrait may have been as a gift to a friend, which was common practice in humanist circles.

A detail of hands from a portrait of Sir Thomas More, 1527, by Hans Holbein the Younger. (Public Domain)
A detail of hands from a portrait of Sir Thomas More, 1527, by Hans Holbein the Younger. Public Domain
More’s political downfall coincided with Henry’s 1531 break with the Catholic Church. The pope refused to grant the king a divorce from Catherine of Aragon so that he could marry Anne Boleyn. After resigning the chancellorship because he was a devout Catholic, More ran into great difficulty in 1534 when Parliament passed a bill that mandated all subjects take an oath that upheld the king’s supremacy over all foreign leaders, including the pope. More’s refusal of the Act of Supremacy led to his imprisonment in the Tower of London for high treason. He was executed in 1535 and is considered by many to be a martyr. Four hundred years later, More was canonized by the Catholic Church.

Thomas Cromwell

A portrait of Thomas Cromwell, 1532–1533, by Hans Holbein the Younger. Oil on oak panel; 30 3/4 inches by 25 1/4 inches. The Frick Collection, New York. (Public Domain)
A portrait of Thomas Cromwell, 1532–1533, by Hans Holbein the Younger. Oil on oak panel; 30 3/4 inches by 25 1/4 inches. The Frick Collection, New York. Public Domain

The engineer of More’s treason trial, though he had implored More during his imprisonment to sign the Oath of Supremacy, was Thomas Cromwell. Cromwell was born into a working-class family, the son of a blacksmith. Thus, his meteoric rise to the upper levels of power as Henry’s closest adviser was astonishing. His career prominence began while working for Wolsey. Though the cardinal fell from favor, Cromwell secured the approval of the king and Anne Boleyn by championing the cause of their marriage. An ardent backer of the English Reformation, Cromwell supported the Act of Supremacy. Later, when Henry tired of Anne and hoped to marry another, Cromwell was the architect of the treasonous charges leveled at Anne, who was beheaded in 1536.

Holbein’s portrait of Cromwell dates to 1532, a year before Cromwell helped arrange the annulment of the king’s first marriage. Compared to More’s portrait, this work has cooler tones and a simpler background, elements that are typical of the output from Holbein’s second English period. Cromwell is depicted with a severe expression. He is shown seated on a bench and separated from the viewer by a table, in contrast to the small ledge in the painting of More that allows for a greater sense of intimacy.

A detail of the alluded coronet (crown) on wallpaper above Cromwell's head, from the portrait of Thomas Cromwell, 1532–1533, by Hans Holbein the Younger.
A detail of the alluded coronet (crown) on wallpaper above Cromwell's head, from the portrait of Thomas Cromwell, 1532–1533, by Hans Holbein the Younger.

Both men hold letters and have a ring on their finger, though in Cromwell’s case these objects, including the bejeweled book in the foreground, emphasize his recent appointment as Master of the Jewel House. Just above Cromwell’s head, one can make out a coronet embroidered in the blue wall covering. This may be an allusion to his political and social ambitions. Cromwell was, in fact, granted the earldom of Essex and made Lord Great Chamberlain in 1540. That same year, five years after More’s death, Cromwell, too, fell from Henry’s favor and was executed at Tower Hill.

Cromwell’s “crime” was his role in organizing Henry’s failed union with Anne of Cleves. Henry’s displeasure with this wife stemmed from high expectations of her beauty that he thought were unfounded upon meeting her. He formulated his preconceived notions from Holbein’s portrait of her. One of the artist’s duties as court painter was traveling throughout Europe to record likenesses of potential brides for the king.

A portrait of Anne of Cleves, 1539, by Hans Holbein the Younger. Oil and vellum on canvas. Louvre, Paris. (Public Domain)
A portrait of Anne of Cleves, 1539, by Hans Holbein the Younger. Oil and vellum on canvas. Louvre, Paris. Public Domain
Another prominent portrait Holbein made of a potential bridal candidate is that of Christina of Denmark, Duchess of Milan. Though a marriage with her did not materialize, Henry kept the portrait until his death. It ended up in the collection of an aristocratic British family. In the early 20th century, the picture was put up for sale and Henry Clay Frick was eager to purchase it. However, there was national outcry at losing such a prestigious work to an American buyer. An anonymous donor contributed key funds to keep the work in Britain and it is now part of the National Gallery in London.
In an episode of “Cocktails With a Curator,” Xavier F. Salomon, deputy director and chief curator at The Frick Collection, explains that Frick was upset at being thwarted in buying this Holbein and consoled himself several years later with the acquisition of the More portrait instead.
A portrait of Christina of Denmark, Duchess of Milan, 1538, by Hans Holbein the Younger. Oil on oak wood; 70 1/2 inches by 32 1/2 inches. National Gallery, London. (Public Domain)
A portrait of Christina of Denmark, Duchess of Milan, 1538, by Hans Holbein the Younger. Oil on oak wood; 70 1/2 inches by 32 1/2 inches. National Gallery, London. Public Domain

Book of Hours

Frick’s subsequent purchase of a Holbein painting, the portrait of Cromwell, has been in the news this year. A previously overlooked prayer book, the Book of Hours, located in Cambridge’s Trinity College Library, has been identified as not only having belonged to Cromwell but also as the volume prominently displayed on the table in Holbein’s portrait.
Book of Hours from the portrait of Thomas Cromwell," 1532–1533, by Hans Holbein the Younger.
Book of Hours from the portrait of Thomas Cromwell," 1532–1533, by Hans Holbein the Younger.

Cromwell biographer Tracy Borman deems it “the most exciting Cromwell discovery in a generation—if not more.” Researchers believe that it is the only object illustrated in a portrait from the Tudor period that survives today. Its provenance can be traced from the time of its donation to Trinity College to the widow of Cromwell’s secretary and protégé.

This printed and illuminated Parisian Book of Hours is exceptionally fine. Its binding is covered with velvet and grossular garnets, and its borders are decorated with silver gilt by a goldsmith who often collaborated with Holbein. Intriguingly, historians believe that both Catherine of Aragon and Anne Boleyn owned copies of the very same prayer book, showing commonality between friends and foes.

The complexities of both Thomases and their portraits remain enigmatic and intriguing. Their current installation at The Frick Madison illustrates the impact of curatorial choice on enhancing the viewing experience.
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Michelle Plastrik
Michelle Plastrik
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Michelle Plastrik is an art adviser living in New York City. She writes on a range of topics, including art history, the art market, museums, art fairs, and special exhibitions.
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