Cowan has painted sixteen monarchs during his sixty-eight-year career. His elite subjects include Prince Rainier III and Princess Grace of Monaco, Augusto Pinochet, Imelda Marcos, the Sultan of Brunei, and His Majesty King Hassan II of Morocco. He’s been handsomely paid for many of these pictures. Your average sheik could spend $250,000 for a portrait of himself, and then be nudged into buying paintings of his brother, his falcon, and four of his favorite horses. 

The artist works in a style he calls “romantic realism.” In his paintings people are twenty pounds thinner and twenty years younger, often surrounded by heavenly light, riding exotic animals, or framed by mountain ranges. This willingness to flout the laws of space and time and his largely unflappable good nature have allowed Cowan to form relationships with the kind of people who will pay for a portrait of themselves with a lion, at the mast of a ship, or gliding through a Venetian dreamscape. 

On display throughout Cowan’s home and adjoining workspace were pictures and memorabilia of his clients, many of whom he considers friends. The photographs both commemorate these relationships and function as visual reminders when Cowan cannot immediately recall an esteemed person’s name. In his painting studio—past the dining room table set for ten with red goblets, out the kitchen door, and across a cement patio—a wide table was crowded with pictures in rusting frames. The day before, while describing for me a portrait of Elvis he sold to “a guy who built all these hotels,” he scanned the cluster of photos—“Wynn!” He had spotted the CEO on the table. It was Steve Wynn who paid $85,000 for the painting of Elvis in his white jumpsuit. 

Cowan’s connections are a big part of the reason people hire him, and many have appreciated in value over the years. Grace Kelly, whom he painted in 1956 and again in 1981, was an ideal subject. The American actress, whose stunning looks and bland public image made her a worthy match for a European prince, satisfied Cowan’s obsession with Hollywood glamour and his desire to rub elbows with royalty. “She called me ‘Maestro’ and I loved it,” Cowan told me. She was also good for business. His status as “official portrait painter to the Family of Monaco” means that all of Cowan’s clients share a portraitist with Princess Grace. An invitation to the palace from Her Serene Highness hung on the wall above the front door. 

Like these pictures and mementoes, all the ornamentation in the house serves a more-than-decorative purpose. Cowan believes his friends and clients expect an artist’s home to reflect his imagination and lifestyle. Behind us, two white columns with gold accents stood in front of ornately framed mirrors. A pair of eight-foot-long tusks framed the archway to the dining room; Cowan assured me they were copies. The rhino head on the wall to my right was also fake, though the antique zebra hide that used to hang below it was authentic. “Animal skins make great backgrounds for paintings, but I got tired of them,” he said.

“I’ve got something on every door,” Cowan told me, and he gestured to a reproduction of Anthony van Dyck’s portrait Charles I at the Hunt on a bedroom door. The monarch looked almost sassy with a hand on his hip. “Nobody ever thinks of a door as a frame for a painting.” 

Cowan first began copying the masters during days spent at the Metropolitan Museum of Art when he was a teenager studying at the Art Students League of New York. He has studied the premier portrait artists carefully, and he is attentive to history. When it was painted, around 1635, Van Dyck’s Charles I was notable for its informal setting and the king’s casual posture. Cowan’s portraits often enhance his subjects’ nobility and splendor, but both artists tend toward complimentary representations. He can’t help but compare himself to the Flemish master. 

“I got a reputation of painting more kings than any portrait painter,” Cowan told me. In case I mistake this for a boast, he clarified that back in the heyday of royal portraiture, travel was so costly and time consuming that even someone as revered as Van Dyck could only hope to visit two or three European monarchs in his lifetime. “It’s not because I’m that good,” he said. “It’s because of airplanes.” 

His ability to be simultaneously irreverent and fawning and, when warranted, intensely loyal has also contributed to his popularity with world leaders. Cowan often takes umbrage at criticism of his more notorious subjects who have shown him kindness. His opinions about a particular queen, businessman, or politician come from personal experience rather than echoing the attitude of a faceless public.

On a small round table in the front room were some photos of standout clients: Cowan with His Serene Highness Prince Albert II of Monaco, son of Prince Rainier III and Princess Grace; Phyllis George, Miss America 1971, who married John Y. Brown Jr., the governor of Kentucky; and Ivana Trump, first wife of the man who has become Cowan’s most controversial and powerful client, the Palm Beach personality who, three days earlier, was elected the forty-fifth president of the United States.

_When Cowan was a boy in Portsmouth, Virginia, his three brothers would go see cowboy movies on Saturdays. He chose the Technicolor musicals showing across the street instead. From an early age, he found that portraiture was the perfect way to combine his passions for painting and celebrity. “I used to love going to the movies and seeing Maureen O’Hara in all these pirate movies and the big ships,” he told me. “I said, one of these days I was going to grow up and meet all these people and paint their portraits—and I did.” 

In the 1950s he painted Debbie Reynolds in casual attire and Liz Taylor in white silk pajamas. The three of them would hang out together in Miami Beach, Los Angeles, and New York City before Taylor ran off with Reynolds’s husband, Eddie Fisher. Cowan wanted to paint Betty Grable, but he says by the time he met her she couldn’t afford it. Elvis paid for his eight-foot-tall portrait with $10,000 in cash and carried it home before the paint was dry. When country singer Kenny Rogers was newly divorced and feeling unsexy, Cowan painted him in a coat that concealed his waistline “and I put a big dick down there,” he said.

I’d arrived at Cowan’s home around noon to find him in the studio at work on a nearly finished portrait of Michel Roger, the former Minister of State of Monaco. In the picture, the politician is wearing a black suit and standing placidly in front of a golden sky more celestial than naturalistic. I dragged over a stool so we could talk while he worked. 

Magazine photos of desert scenes, jewelry ads, and paparazzi shots of British royals were taped to the edge of a table and had formed a thick fringe off the side. Cowan had hundreds of classic films and musicals on VHS stacked on a shelf in his studio, and a video compilation of songs from Andrew Lloyd Webber musicals blared from a big-screen TV across the room.

Cowan dabbed at the crest of Monaco he was adding to the corner of the Roger portrait. On the table to his right was his palette, a piece of plexiglass covered in globs of apricot- and rust-colored paints. Everything in the studio was worn, dusty, and dotted with flecks of paint, except for the dozens of completed paintings displayed under spotlights or propped against the walls. 

At five years old, Cowan taught himself to paint with a set of oils he found at church. His ultra-religious parents discouraged it. When he was eight, he painted a ship sailing against a background of clouds on his bedroom wall, and his mother threatened to whip him. “My father kept saying, ‘artists are a dime a dozen.’ His whole line was ‘get a job,’” Cowan said, as he put down his brush. “I’ve gotta let that dry.” He’d smeared a bit of red across some wet white paint. “Dammit. It puts me back one more day, but I don’t have to have this finished at a certain time.”

Cowan had been asked to donate the portrait of Roger, but he does not paint anyone for free. Once the country of Monaco had raised the funds to pay for the painting, he got to work. Michel Roger was not present. Cowan typically paints from photographs rather than live models. Few rich, powerful people have the time to model for a portrait, and few painters want their rich, powerful subjects in the room while they work. Cowan does travel to meet his subjects, however. Depending on their wealth and status, this could mean an afternoon taking photos at their home or several days spent touring a palace and attending banquets. Then he returns to West Palm Beach to paint. 

Hanging above his easel was a partly finished portrait of Pope John Paul II created for one of Cowan’s most treasured clients, the former first lady of the Philippines, Imelda Marcos. Once lauded for building “welfare villages” and a multimillion-dollar cultural center, now ostracized for cronyism and excessive luxury (she famously spent $2,000 on gum at the San Francisco airport), Marcos first commissioned Cowan to paint her portrait in the early 1980s. He waved away my question about her legacy of corruption. “I found her to be one of the sweetest, most knowledgeable people. She would know what the short-term political outcome is gonna be, and the long-term one, and she built all these recreation centers for her people,” he said. When I had planned this trip months earlier, and even as I packed on the afternoon of November 8, I had imagined that this indifference to fraud and graft would place the artist on the wrong side of history. However, less than one hundred hours after the 2016 election, my assumption that virtue overcomes corruption seemed utterly naive.

Cowan has completed at least seven portraits of Imelda Marcos and her family, some supposedly after she was forced into exile following mass protests over rigged elections and human rights abuses. (He has refused to paint two world leaders: Fidel Castro and Muammar Gaddafi.) Marcos had also facilitated a number of paintings of world leaders and royalty, by commissioning them herself or introducing and recommending Cowan to the client. In addition to Pope John Paul II, the list includes Mikhail Gorbachev, whom he painted as a gift from Marcos in the mid-1980s; the Sultan of Brunei, at the time the richest man in the world; Ronald and Nancy Reagan; and His Majesty King Hassan II of Morocco, whom Cowan has painted three times. 

“These people, everything they want they already have it, but very few people in very few countries get good portraits,” Cowan explained. Marcos commissioned him to paint her friends, “because she could give them something that was going to just knock ’em to the floor.” In return, he said, “she might ask for a fleet of airplanes or something else for that favor—I never knew what she was up to.” He laughed. In The Painted Face, a book about Cowan’s life and work that his manager, Steve Mohler, wrote and self-published in 2015, there is a photograph of Imelda Marcos introducing Cowan to Adnan Khashoggi, the Saudi arms dealer and alleged weapons smuggler who was indicted in U.S. federal court—along with the president and first lady of the Philippines—on charges of racketeering, corruption, and obstruction of justice. 

While Cowan and I were talking, Mohler came in to check on us. The artist had a stroke in 2013. His hands are steady, but he can paint for only a few hours at a time. He was done for the day, so Mohler scraped a glob of white paint off the canvas and wiped it on the palette, which he placed in the freezer. Cowan directed him to take the painting into the kitchen to dry.

Cowan has come to depend on Mohler for help with his day-to-day tasks and business, and Mohler credits Cowan with saving him from a boring corporate job. Twenty-eight years ago, he knocked on Cowan’s door selling insurance. The painter answered wearing red silk pajamas and invited him inside. Mohler stayed there all day trying to fill out the insurance forms. Every question led to a lengthy digression, but he didn’t mind. The following week Cowan took him to lunch and asked if he’d ever considered working with an artist. “I guess he knew he was difficult and needed someone patient,” Mohler said.

“Steve, she’s asking me the most god-awful questions about my parents beating me,” Cowan complained in mock anguish. I had asked about his childhood, but he’d volunteered the stories of corporal punishment. “Oh really?” Mohler replied with a tone of benevolent distraction. He has pale blue eyes and light brown, curly hair. Though he frets over signs of aging, he looks young for fifty-four. He was excited to show off Cowan’s work, and he pulled one of his current favorites off the shelf. It was a surrealistic landscape in which a blue ball and a soccer cleat float next to a shirtless man with a perfectly chiseled body.

Cowan and Mohler occasionally have heated arguments over things like travel plans and fee negotiations, which Cowan attributes to Mohler’s inability to transcend his ego and Mohler blames on Cowan being an artist who is too emotional to see the bigger picture. But Mohler plans to stick with Cowan until the artist dies—a subject they discuss often. 

“I asked Steve, ‘What are you gonna do with all the photographs after I die?’” Cowan said, referring to the framed pictures of his clients crowded on the table next to him. Mohler teased: “I’m going to get a big trash bag for them.” 

_“Certain people, I don’t like to talk about, because nothing good happens to me from talking about them,” Cowan said. We’d left the studio to have lunch at an Italian restaurant near the house. That afternoon, Mohler had agreed to take me to see the portrait of Donald Trump that hangs in the Mar-a-Lago library, and Cowan was dodging my questions about the painting and its subject. “I don’t let anybody say anything unkind about anybody I’ve painted,” he said with another wave of his hand and then launched into a story about swordfighting with Tyrone Power on a tall ship in the Bermuda Triangle. 

After lunch, Mohler dropped Cowan at home, and he and I drove south to Mar-a-Lago, Trump’s private oceanfront club in Palm Beach. The property was built in 1927 by General Foods owner Marjorie Merriweather Post; Donald Trump bought it from Post’s daughters in 1985 for eight million dollars, furniture included. He keeps a residence on the seventeen-acre estate, but it mostly serves as a lavish private club and event space. Today, members pay a $200,000 initiation fee (the price doubled one week after Trump’s inauguration) and $14,000 in annual dues for access to the pristine beach and the “Trump Spa and Salon” and for golf privileges here and at eight other Trump Golf courses around the world. 

Like much of the rest of the country, the small, tony community of Palm Beach was still coming to grips with the fact that one of its most substantial and controversial property owners was going to be president. Entry to the club was heavily restricted. “We’re very lucky. [They’re] bending the rules for us,” Mohler told me as he arranged our visit. I was appreciative of Mohler for being such a gracious host, but I did not feel lucky. I felt sick. Still, I was determined to see the painting, now one of Cowan’s most famous works. 

On the way to the club we picked up a friend of Mohler’s, socialite and local real estate agent Pamela O’Connor, at her 1940s Art Deco home near Worth Avenue, Palm Beach’s luxury shopping district. Cowan has painted portraits of O’Connor, her son Morgan, and her mother. O’Connor describes herself as “eccentric” and told me she recently moved to a house near the water in West Palm Beach because Morgan, a former Ralph Lauren model and aspiring musician, is currently staying in the family home. She is his manager and the previous night, while talking with a music producer on his behalf, she got emotional when she heard Trump’s helicopters overhead. “That’s our president,” she thought, but stopped herself from saying it out loud, assuming the woman she was talking to wasn’t a Trump supporter. Like many on the island, she’s crossed paths with Trump over the years. “I think he can be good,” she said. 

“I wish I’d joined when it only cost $50,000,” O’Connor murmured as we turned onto Ocean Boulevard. We passed colorless, sprawling homes cordoned inside the ubiquitous green hedges that conceal some of the world’s wealthiest people from our prying eyes. “That is Yoko Ono’s house—or it was. And there’s the Woolworth home,” Mohler said. 

Cowan had moved to the Palm Beach area expecting that proximity to extreme wealth would be good for business. It hasn’t quite worked out that way. While he has painted some prominent locals, he’s struggled to break into the more established and exclusive social circles here. Unlike families who for generations have wintered in Palm Beach and summered in Newport or Saratoga or Nantucket, Mohler said he and Cowan feel more comfortable with “rich people who started off more modest.” This describes many Mar-a-Lago members. 

Thinking the best way to make inroads with this crowd was through its owner, Cowan pursued Trump as a client. When he’s after a commission, Cowan told me, “I don’t take no for an answer. If you slam the door in my face, I go around to a window. If you slam a window, I go to the top of the house and come down the chimney. I keep going until I get the portrait. I never get mad if somebody says ‘no’ to me,” he said. This can take years, and while Cowan doesn’t mind waiting for a commission, he does not like to cut a deal. In the late eighties, Donald Trump agreed to be painted, but he didn’t want to pay full price. 

There have been conflicting news reports about the negotiated fee for the painting and about Cowan’s attitude toward Trump. Cowan and Mohler do not like to say what he was paid for particular works because his prices have gone up over time. They confirm that Trump received a sixty percent discount on the piece; once Mar-a-Lago became a private club, the artist was given regular access. (Later, Trump paid Cowan a negligible amount to have his hand, which Cowan had originally sketched in sepia, painted over in oil.) Cowan has grumbled about the way Trump does business. Mohler, however, believes that a de facto membership to the club is worth more than a portrait’s fee, as it allows them to meet potential clients. Cowan says Trump has also referred to him as “the greatest portrait painter.”

Under the ornately carved and gilded wooden ceilings, the Mar-a-Lago receptionist and a few staff members were quietly chatting. Mohler rushed us past walls tiled in elaborate, Mediterranean-inspired patterns and into the library. On a wall paneled in dark wood, one of the few surfaces in the club smooth enough for a portrait, hung the painting of Trump.

The picture is of a man younger, slimmer, and possessing a complexion significantly healthier than today. He is wearing a white V-neck tennis sweater; Cowan had been adamant about painting Trump in casual clothes, his Palm Beach look. Behind him is a standard Cowan sky shot through with beams of divine light. “I’ve been in other homes in Palm Beach—same exact painting,” Mar-a-Lago butler and historian Anthony Senecal told the New York Times of the portrait, and this is basically true. 

Our pretense for visiting was to take photos in front of the portrait, and as Mohler snapped away, the news of the president-elect’s first visit to the White House played on a television above the bar. On our way out, O’Connor left a note for Trump at the front desk, telling him she was Ralph Wolfe Cowan’s friend and that Cowan had painted her son’s portrait. 

“Has Ralph painted the children, too?” she asked Mohler. 

“Everyone but Barron,” he replied. 

“He’s a very good-looking boy—well, they’re all good-looking,” O’Connor remarked. 

Several times during my visit Cowan reminded me that few people know what they actually look like and that even fewer would pay for a realistic painting of their true selves. But in a world that believes beauty, power, wealth, and virtue are correlated, artful obsequiousness can take you to weird and wonderful places. Here, flattery is the local currency. In moments when I’d spent some myself, with an insincere compliment or a smile to disguise my disapproval, I could feel who I wanted to be—independent, critical, strong-willed—superseded by who I feared I was—obliging, avoidant, submissive. One of the keys to Cowan’s success is that most of the time his unctuousness is genuine. His warm feelings toward many of his subjects are enhanced by the belief that generous and good-natured rich and powerful people are even more virtuous than your average nice guy or girl because, being so rich and powerful, they don’t have to be kind. 

As the car pulled out of the Mar-a-Lago driveway, we kept pace with a yacht cruising on the emerald green water to our right. It was the epitome of romantic realism. In Palm Beach during the first days after the 2016 election, corruption and cruelty had been expertly painted under a halo of clouds and a bath of heavenly light.

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