All portraits depend on the collaboration of artist and sitter, but rarely do both parties appear to be having so much fun as in John Singer Sargent’s second portrait of the Anglo-Jewish heiress Ena Wertheimer, a work of 1904 that he playfully gave an Italian title, A Vele Gonfie—“in full sail” (see illustration below). Though in 1904 Sargent also declared himself “sick of portrait painting,” A Vele Gonfie betrays no sign of that disaffection, unless one considers the exuberance with which the image sends up the conventions at which its maker chafed. “The only expression allowable in great portraiture is the expression of character and moral quality, not of anything temporary, fleeting, accidental,” Sargent’s fellow artist Edward Burne-Jones had decreed toward the end of his career; but if the reports of A Vele Gonfie’s origins are to be credited, it was precisely the fleeting impression of how Ena swept into his studio, clothes billowing behind her, that Sargent sought to capture in paint. Rather than highlight the expanse of his subject’s bare neck and arms, as he had done in his earlier portrait of Ena with her younger sister Betty, he chose to exploit the potentially androgynous allure of her six-foot figure by transforming her—with her evident complicity—into a dashing cavalier.

Portrait of Ena Wertheimer (A Vele Gonfie); painting by John Singer Sargent

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John Singer Sargent: Portrait of Ena Wertheimer (A Vele Gonfie), 1904

Paintings are not snapshots, of course, and this effect of spontaneity is itself an artifice. The cloak that seems to puff out “in full sail,” for example, is apparently held in place with the aid of a broomstick that the artist instructed his sitter to hold—though “sitter” is hardly the appropriate term for Ena in this particular encounter, as Jean Strouse aptly observes in Family Romance. (Some viewers, she reports, understandably mistook the broomstick for a sword.) Nor, presumably, did the eldest daughter of the Wertheimer clan burst into Sargent’s studio dressed as a member in good standing of the Most Noble Order of the Garter. The painter was simultaneously at work on an official portrait of the Marlborough family that the duke had commissioned as a pendant to one painted for an ancestor by Sir Joshua Reynolds over a century earlier, and the evidence suggests that it was his plumed hat and robe—“or improvised copies”—that the pair mischievously adopted for A Vele Gonfie.

To compare the liveliness of such a picture with an exercise in dynastic portraiture like The Marlborough Family (1904–1905) may seem unfair, especially since the duke had summoned Sargent to commemorate a family on the verge of collapse: having entered into an arranged marriage with the wealthy American heiress Consuelo Vanderbilt in order to preserve his Blenheim estate, he had long been estranged from his unhappy wife, and the couple officially separated the year after the painting was completed. But to turn from the spirited performance of A Vele Gonfie to the aristocratic formality and stiff poses of The Marlborough Family—a contemporary observer called the duchess “a simpering doll”—is to understand what the artist meant when he took to writing dismissively, in private correspondence at least, of “paughtraits.” To juxtapose the two paintings is perhaps also to sense what the poet and polemicist Wilfrid Scawen Blunt had in mind a few years later when he remarked about a portrait of the former Aline de Rothschild, now Lady Sassoon, that Sargent “paints nothing but Jews and Jewesses now and says he prefers them, as they have more life and movement than our English women.”

Blunt’s report of the artist’s clientele was wildly exaggerated. Strouse calculates that no more than 5 percent of the sitters for the approximately 1,300 oils and charcoals that Sargent produced were Jewish. But among that 5 percent was the artist’s greatest patron, Asher Wertheimer, a wealthy London art dealer of German Jewish ancestry and the patriarch of the family whose story Strouse sets out to tell. Between 1896, when Asher ordered portraits of himself and his wife, Flora, to celebrate their silver wedding anniversary, and 1908, when the painter completed an Orientalized image of one of the couple’s younger daughters, Almina, Sargent produced a dozen paintings of the Wertheimer clan: the single largest such commission, viewed collectively, in the artist’s prolific career. A Vele Gonfie, which Asher presented to Ena as a wedding gift on the occasion of her marriage to Robert Mathias in 1905, was the tenth in the series. By the time Sargent put the finishing touches on the picture of Almina, he had spent over a decade engaged in what he jokingly termed “chronic Wertheimerism.” Asher in turn chose to hang most of the series in his dining room at Connaught Place, where their creator was such a frequent guest that it became known as “Sargent’s Mess.”

In 2015 the National Portrait Gallery in London and the Metropolitan Museum in New York sought to unsettle the received view of Sargent as a fashionable recorder of high society by jointly organizing an exhibition focused on his more experimental portraits of artists and friends—portraits, they emphasized, that were typically not commissioned but originated with the painter himself, often as a gesture of friendship to the subject. According to an anecdote recorded in the catalog, a visitor to his studio once pointed to a portrait of a society hostess and asked how he could bear to paint like that, when he could also paint the portrait of the musician George Henschel that hung nearby. “I loved Henschel,” Sargent simply replied.1

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But while the inscription “to my friend Henschel” implies that the musician’s portrait probably did serve as a gift, the line between painting for love and painting for money in Sargent’s case proved hard to maintain—a fact that the organizers of the exhibition implicitly acknowledged when they chose to include the painting of Asher among their “Portraits of Artists and Friends.” Though he was one of the most knowledgeable art dealers of his day, Asher was certainly not an artist himself, and it seems clear that there would have been no commission in the first place had he not been able to afford Sargent’s asking price, which Strouse reports was typically one thousand guineas per portrait in the late 1890s (approximately $170,000 today). As the commissions multiplied over the following decade, a considerable sum of money must have passed from Asher’s pockets to Sargent’s. Yet Strouse’s account of their relation is not simply a chronicle of artistic patronage. As the title of Family Romance implies, something like friendship, too, was in the air when Sargent painted the Wertheimers.

Having previously written acclaimed biographies of Alice James and J.P. Morgan, Strouse was in one sense entering familiar territory when she set out to reconstruct the Wertheimers’ world. Like Sargent, as she notes at the outset, both her previous subjects were Americans who lived transatlantic lives in the latter half of the nineteenth century and the first decades of the twentieth. Alice’s brother Henry, the novelist, was a good friend of the painter’s and an avid supporter of his work; Morgan was a prominent art collector as well as a financier and banker. By Strouse’s own account, her curiosity about the Wertheimers was also piqued by the sense of recognition the portraits elicited when she first encountered them at a traveling exhibition in Seattle more than two decades ago and saw features familiar to her from the German Jewish milieu of her childhood.

But a biographer needs more than affinity for her subject: she also requires documentary evidence. And in that respect at least, the Wertheimers initially appeared quite unpromising. Nothing like the reams of writing left behind by the Jameses or the “vaults” of uncataloged documents that Strouse discovered in the Morgan Library when she embarked on her biography of the banker has survived from Asher and his descendants. Though she did manage to turn up some unexpected finds, including a cache of letters from Sargent that she was the first to succeed in transcribing (their previous owner had found his handwriting indecipherable) and then serendipitously acquired for herself, the written record remains sparse. Indeed, one of the puzzles Family Romance helps to solve is why the Wertheimers, who in their day rivaled firms still storied in the art world like Knoedler or Agnews, more or less vanished from public consciousness—except, of course, as a collective subject of Sargent’s brush. Portraitists are often employed with posterity in mind, but Asher may have chosen even more wisely than he knew when he decided to commemorate twenty-five years of marriage to the daughter of another art-dealing dynasty by ordering up two portraits by Sargent.

The couple weren’t altogether happy with the painting of Flora—she reportedly thought her lace-trimmed gown, adorned with diamonds and pearls, made her look “too rich”—and six years later Sargent was invited to produce a second version, clad in sober black, that apparently met with more favor. Publicly, however, it was Asher’s portrait that was apt to provoke controversy. Dressed in black, a gold watch-chain dangling from his waistcoat, the subject emerges from a dark background with an amused gleam in his eye as he pinches a cigar between his fingers and gazes confidently at the viewer. A large black dog stands at his side, its long pink tongue contributing to the partly comic effect, even as it threatens to echo—and exaggerate—the moist red lips of his human companion. Hovering between caricature and an exercise in grand portraiture in the tradition of Titian and Velázquez, the painting has long tended to divide its viewers, functioning as something of “a cultural Rorschach test”—the phrase is Strouse’s—for perceptions of antisemitism.

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When Asher’s portrait was first exhibited at the Royal Academy in 1898, The Athenaeum could hardly contain its enthusiasm. Invoking the painting’s “profound and courageous sense of humour” and “extraordinary simplicity of technique,” the review concluded by cheerfully hailing the subject of this “masterpiece”: “Happy is the man whose portrait has been painted thus.” But other observers were far less ready to sing its praises. The American architect I.N. Phelps Stokes, who figured in a double portrait by Sargent painted around the same time, saw the unfinished picture of Asher in the artist’s studio and remarked that he seemed “pleasantly engaged in counting golden shekels.” A Punch cartoon of 1898 under the heading “Unconscious Humour at the Royal Academy” enlarged the sitter’s nose and paunch, replaced the cigar with coins, and added a speech bubble in the form of a caption. “What only this monish [money] for that shplendid dog,” the figure appears to be saying: “Ma tear it is ridic’lush!” When Asher later pledged nine of the Wertheimer portraits to the nation, a member of Parliament dispensed with the joking and simply demanded that the authorities store the “repulsive” paintings out of sight.

Asher Wertheimer; painting by John Singer Sargent

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John Singer Sargent: Asher Wertheimer, 1898

Writing of Asher’s portrait in a book revealingly entitled John Singer Sargent: The Sensualist (2000), one of the artist’s most acute critics, Trevor Fairbrother, observed that the sitter’s “Jewishness, masculine self-confidence, entrepreneurial power, and sensuousness all radiate from the picture,” and despite the alarms that cluster of nouns might set off, the evidence suggests that Asher was inclined to agree. (Elsewhere Fairbrother has termed the dog, a black poodle named Noble, “the happiest pet in all of Sargent.”) The Wertheimers were clearly capable of registering their dissatisfaction with a picture—witness the request for a second attempt at Flora—but rather than seek out a more conventionally flattering portraitist, Asher responded to Sargent’s work by ordering up ten more portraits over the following decade. Not all of these have the vitality of Asher Wertheimer, but the best of them, like A Vele Gonfie and the double portrait of Ena and Betty, are among the most arresting images Sargent painted. Though Strouse reports that some of the Wertheimers’ friends took offense at Sargent’s portrayal of Asher, his decision to memorialize himself by bequeathing the portrait to the nation testifies that he felt otherwise.2

Most of what we know about Sargent’s side of the relationship must be deduced from the paintings themselves, but Strouse’s book helps to fill in the picture. His mock complaint about “chronic Wertheimerism” notwithstanding, the evidence she has collected tends to confirm that he, too, shared in the high spirits and sense of warmth captured by his portraits of Ena and Asher. Sargent seems to have been particularly close to Ena—so close, in fact, that her husband later wondered if they had been lovers, though the Wertheimers’ apparent lack of concern about this testifies to the easy rapport they seem to have established with the artist. An anecdote variously attributed to Flora in the early days of the friendship and to Betty after Ena’s death suggests that the family had a standard response to such worries. “Of course not,” Flora replies in one version of the story, “he’s only interested in Venetian gondoliers.”

Robert’s question about his late wife’s sexual history appears to have been motivated by his discovery of the same cache of seemingly illegible letters that Strouse later deciphered. But rather than a scandalous secret, the brief extracts she reproduces offer intimations of the playfulness—and exuberance—on display when the artist painted his favorite Wertheimers. Over the course of his career, Sargent produced some spectacular portraits of sisters: Henry James’s first view of The Wyndham Sisters at the Royal Academy in 1900, for instance, prompted him to compare the experience to watching “the lady…shot from the cannon.” But while it was clearly the artist’s bravura performance that blew James away, viewers’ responses to the double portrait of Ena and Betty appear to have been provoked by artist and subjects alike.

The picture shows the two women boldly striding forward, Ena’s arm wrapped around Betty’s waist, their low-cut gowns a vivid juxtaposition of gleaming ivory and crimson that simultaneously heightens and reverses the contrast between the rosy-cheeked older sister and her paler sibling. When Ena and Betty, Daughters of Asher and Mrs Wertheimer (1901) took its turn at the Royal Academy, The Times pronounced it “instinct with life,” a verdict that even Roger Fry, who typically had no use for Sargent, managed to echo when he followed up his qualified praise of the picture—“in its way a masterpiece”—by remarking on its subject: “The poses of the figures are full of spontaneity and verve, and the contrast between the leaning figure of the younger girl and the almost exaggerated robustness of her sister is entirely felicitous.” As Strouse pointedly observes, “the lacy strap sliding off [Ena’s] right shoulder summons the ghost of Madame X,” whose similarly placed strap had precipitated a minor scandal at the Paris Salon almost two decades earlier. But rather than “the icy artifice” of that “professional beauty,” with her “powdered pallor, theatrical sexuality, and air of arriviste hauteur…these young women are warm, natural, radiantly alive.” Unlike that solitary beauty, one might add, they face the viewer directly, and what they are proudly putting on display is also their affection for each other.

It’s easy to imagine why Sargent might have been drawn to their company. In an influential essay on the painter timed to coincide with his first professional visit to the United States, James simultaneously paid tribute to the “slightly ‘uncanny’ spectacle” of his young friend’s talent and worried that that very precociousness might tempt him to relax and take things easy. “Having knowledge to spare he may be tempted to play with it and waste it,” the novelist brooded, but to judge by the rest of Sargent’s career, more play—James’s other word was “larkiness”—may have been just what was needed. Though Asher’s commissions might not have afforded Sargent the kind of freedom he eventually attained when he took off for the Continent and plein air watercolors, the informality of the Wertheimer household must still have been a welcome respite from the constraints of aristocratic portraiture.

At the time he was painting Ena and Betty, Sargent brought Claude Monet, who was in London for his Houses of Parliament series, to dine at the Wertheimers’. (The two had known each other for a quarter-century, ever since the twenty-year-old Sargent had excitedly rushed up to the older artist at a gallery in Paris.) Monet later wrote an enthusiastic account of the occasion to his wife:

The house is indeed quite extraordinary, a palace with some very beautiful things and a quite distinctive society, nothing but Jews, or almost, an infernal din and very relaxed manners despite a high degree of elegance, ten children, five daughters, three of them married and several quite beautiful; dinner lavish and quite good…. As Sargent and I were leaving, they sat down to play games. It’s a really extravagant, crazy place; the father and mother are good people.

Monet’s numbers are slightly off—there were six daughters, not five, and only one was married at the time—but he still appears to have gotten the atmosphere right. When Sargent once told Ena that he would try to stop by after dinner, “& if I do I shall crawl in on all fours straight to you,” he was writing very much in the same spirit.

Of course, the Wertheimers hadn’t always lived on such a lavish scale. Strouse closes her narrative by invoking “a world in radical flux,” and it was the mobility of that world—not just the social mobility but the physical circulation of people and art objects alike—that brought an expatriate artist like Sargent into conjunction with a family like theirs. Though Asher could trace his lineage back to a distinguished rabbi and financier, Samson Wertheimer, whose service as a “court factor” to three Holy Roman Emperors had earned him the title of Judenkaiser (emperor of the Jews), his own father, also named Samson, had simply identified himself as a “merchant” when he emigrated from Bavaria to England in 1839. Like many such immigrants, this Samson settled in the East End of London, married a woman from his native town, and proceeded to work his way up, moving first from Spitalfields to Soho and then to Mayfair as his fortunes improved.

Specializing in decorative objects made of bronze, including the gilded type known as ormolu, Samson ran his shop with the aid of craftsmen recruited from Paris, and by 1854 he had acquired a royal warrant, signifying that his firm had supplied goods or services to royal households for at least five years. Two decades later he received a commission to redecorate Clarence House, the neoclassical mansion in which the present king and queen have chosen to remain rather than move to Buckingham Palace after Charles’s coronation.

Among Samson’s other valuable clients were Lionel and Anthony de Rothschild, and Rothschilds continued to cross paths with the Wertheimers, both professionally and socially, for over half a century. Indeed, the Rothschilds’ reliance on the Wertheimer firm became such common knowledge that when Samson paid 9,900 guineas in 1887 for a portrait by François Boucher, The Times of London mistakenly reported that he was acting as their agent, only to issue a hasty correction: “Mr. S. Wertheimer, of…New Bond-street” had purchased the portrait of Madame de Pompadour “on his own account.” After his death five years later, the same paper duly took note of the impressive stock Samson had left behind: “Messrs. Wertheimer have always been fastidious buyers, and there is surprisingly little in the collection that can be set down as common or ordinary.”

Though both of Samson’s sons followed him into the business, it was Asher, rather than his older brother Charles, who succeeded in building on that legacy. While “wicked Uncle Charlie,” as he was known in the family, traded—sometimes dubiously—from the treasure-filled home into which he had settled with his mistress, Asher took over his father’s Bond Street gallery and proceeded to make some remarkable purchases. Among the most important was a collection of eighty-three Dutch and Flemish paintings that had been amassed over generations by a family of Scottish bankers and traders named Hope, who had settled in Amsterdam before moving to England at the close of the eighteenth century. The Hope collection included pictures by Rembrandt, Vermeer, Rubens, and Van Dyck, as well as other famous artists, and its appearance on the market had understandably aroused stiff competition. But if Asher’s success is a tribute to his acuity, the subsequent history of the transaction also helps to explain why the Wertheimer firm may have left fewer marks on the official record than some of its less scrupulous rivals.

Though the story is somewhat tangled and hard to reconstruct, Asher seems to have invited one of those rivals, P. & D. Colnaghi, to share in the purchase—probably, Strouse speculates, in order to help with the placement of so many pictures—only to have Colnaghi proceed to cut him out of the negotiations and offer the best works to its own clients. In addition to a Colnaghi partner named Otto Gutekunst, the participants in this scheme notably included Bernard Berenson, who operated with his characteristic slipperiness, especially when it came to fronting for the firm with the distrustful Isabella Stewart Gardner. Having previously been burned by Colnaghi, Gardner wanted nothing to do with it, but Berenson shamelessly lied his way into the deal, inflating both prices and his own involvement in the process. At the same time, another Colnaghi partner was busy elbowing Asher aside in negotiations with the distinguished director of the Gemäldegalerie in Berlin, Wilhelm Bode, despite the fact that the Wertheimers had been working with Bode for over a decade.

Since the Wertheimer records have disappeared, Strouse has to deduce Asher’s side of the story from the evidence left behind by others, but she argues plausibly that he lost out because he lacked the aggressiveness and capacity for self-promotion required to maneuver amid “the brutal tactics of the modern competitive marketplace.” Her narrative suggests, in fact, that his comparative lack of aggression and the gaps in the documentary record are related. “The Colnaghi partners commandeered the Hope sale so thoroughly,” she writes, “that Asher’s name has been obscured in accounts of it for more than a hundred years.”

Between his experience with Colnaghi and a protracted lawsuit to recover an unpaid debt that also involved some shady moves by his estranged brother, Asher seems to have decided that he preferred quietly financing deals behind the scenes rather than actively participating in them up front—yet another reason, of course, why his name could sometimes disappear from the official record. Though Strouse reports, for instance, that he jointly purchased Vermeer’s Mistress and Maid with the London art dealer Arthur J. Sulley before selling it to the German entrepreneur from whom it was later acquired by Henry Clay Frick, Asher’s part in the affair doesn’t currently appear in the account of the painting’s provenance on the website—essentialvermeer.com—that otherwise documents such matters meticulously. The site does, however, credit Asher together with Colnaghi for the transaction that resulted in transferring Vermeer’s The Glass of Wine from the Hope collection to the museum in Berlin.

Nor did the rules of patrilineage help to perpetuate the family name, despite the fact that the Wertheimer brothers had six sons between them. Asher and Flora’s eldest son, Edward, had been destined to take over the firm, but he had barely begun his career when he died of typhoid contracted from eating raw shellfish on his honeymoon in Paris. (Sargent’s portrait of Edward, who was twenty-nine at the time, remains appropriately unfinished.) The loss was all the more poignant because it had been preceded some four months earlier by the death of the Wertheimers’ second son, Alfred: a more troubled figure than Edward, he had quarreled with his father over his wish to be an actor and overdosed on morphine at the age of twenty-six. Sargent, whose portrait of Alfred had turned the young man into a minor celebrity when it appeared in 1902, apparently tried to mediate between father and son, to no avail.

Both of Charles’s sons also died childless within five years of each other, reportedly from typhoid, though Strouse speculates that the official explanation in their cases may have been a screen for suicide. The only males of their generation to outlive their parents were Asher’s two younger sons, Conway and Ferdinand (“Bob”), but since they responded to the outbreak of World War I, as did other British Jews at the time, by anglicizing their names, they too helped to obscure the Wertheimer inheritance. Neither one had any children, so the Conways, as both confusingly chose to call themselves, died out as well. Ena, on the other hand, managed to produce five children in seven years, but these, of course, were not Wertheimers, though their rapid appearance did occasion a further bit of playfulness from Sargent, who mischievously coined the term philoprocree—lover of procreation—in order to inscribe a sketch of their mother.

Of all Asher’s offspring, it was Ena who came closest to perpetuating his legacy, even if she didn’t do so as a Wertheimer. Her initial hopes of becoming a painter may have been dashed when Walter Sickert, with whom she studied at the Slade, told her she’d “better go home and learn how to wash and iron,” but she seems to have had no intention of settling in as a housewife. Seven years after her father’s death, she, too, opened a gallery and marked the event with a loan exhibition of works by Sargent, who had died just a few months earlier. Tellingly, however, the show primarily featured his watercolors rather than portraits in oil: a choice underlined by the accompanying catalog, which made a point of the liberation they represented. Questioning whether “the real John Sargent” was “the rather unapproachable chef d’école in his great studio or the happy wanderer in his gondola moored off the Salute, painting furiously between sun and water,” the catalog went on to announce that, in the present show, “we shall only find…the great man at play” and will be “free to enjoy ourselves with something of the pleasure that was his as he worked.”

The avowed aim of Ena’s gallery was to promote the work of younger artists, and whether or not she consciously intended the show as a farewell gesture, that is more or less how it functioned. A week after it closed, the gallery followed it with an exhibition of stage designs for the Ballets Russes, whose founder, Serge Diaghilev, had become a friend and frequent guest at Ena’s dinner table. Subsequent shows included work by Fernand Léger, Raoul Dufy, Pavel Tchelitchew, Ben and Winifred Nicholson, and Vanessa Bell, among others. One acquaintance dubbed Ena “a kind of high priestess of modern art,” and from the perspective of art history, there is something satisfying about the way in which a woman once close to Sargent now socialized with the likes of Diaghilev and Picasso.

But it’s harder to understand—and forgive—her decision to sell off A Vele Gonfie. Though Strouse speculates that she may have intended the proceeds to support the new gallery, she also notes that Ena was a wealthy woman with a generous inheritance. Perhaps the fact that her less aesthetically adventurous husband opposed the sale encouraged her decision, since the couple were by this time increasingly at odds.3 That Sargent had been aware of Ena’s wish to “get rid of” the picture before his death—the phrase is his—only deepens the puzzle. To quote her otherwise sympathetic biographer: “How could she?”