Skip to main content

Charting Meghan Markle’s rise from Hollywood nobody to Duchess-to-be

Meghan Markle had had it with Hollywood—big-time. She’d just turned twenty-nine. It had been seven years since she’d graduated from the prestigious Northwestern University in Chicago with a double major in theater and international studies, and instead of being hailed as the next Angelina Jolie, she was stuck in the professional equivalent of Nowhere-stan.

Four years after her General Hospital debut, she was still hoofing it as one of twenty-six “briefcase girls” wearing a shimmery sateen minidress and gold stilettos on the NBC game show Deal or No Deal. The girls—all beauties, but none as viv­idly gorgeous as number twenty-four, Meghan Markle, with her blaz­ing smile—were required to descend a neon-lit staircase en masse at the opening of the show to a raucous soundtrack of pelvic-thrusting electronic guitar music, and chorus “Hi, Howie!” at the rollicking game show barker Howie Mandel. The girl who opens the winning silver briefcase holding anywhere between one cent and a million dol­lars gets the most airtime. “I would end up standing up there forever in these terribly uncomfortable and inexpen­sive five-inch heels just waiting for someone to pick my number so I could go and sit down,” she has said.

Backstage, the other briefcase girls noted that she was always working, reading scripts, calling her agent, or practicing her lines for her next audition. At night, she would go home and write a doleful anonymous blog about her rejections under the title The Working Actress. “I’ve had to freeze my [acting] union membership, borrow money, work jobs that I hated, endure being treated like s**t on a set, kiss actors with smelly breath and cry for hours on end because I just didn’t think I could take it any more,” la­mented one entry. To make extra money, she freelanced as a calligra­pher writing out wedding invitations and Dolce & Gabbana holiday correspondence.

From 2002 to 2011, Meghan’s show clips are a parody of a young actress trapped in the male gaze. A 2006 episode of the CBS crime pro­cedural CSI: NY features her wearing a sexy maid’s outfit and deliver­ing the line, “I may have slept with Grant Jordan, but I didn’t kill him.” In a 2008 episode of the Fox sitcom ‘Til Death, she’s a car salesperson in a tight blue bustier over a T-shirt stroking a red open-topped Cor­vette. Her opening gambit, “You fellas interested in checking this baby out?,” earns the reply, “We’re here for donuts so you can save your seductively minty breath.” In the morose 2010 melodrama Remember Me, panned for its “thunderously overwritten screenplay,” she plays a bartender with one line and an attitude. In Horrible Bosses, shot the same year, she has a thirty-second cameo in a baseball hat on the receiving end of Jason Sudeikis’s assessment, “You’re way too cute to be just a FedEx girl.”

In The Palace Papers, Tina Brown sheds new light on the royal family’s major players

In the early years of her career, her ambiguous ethnicity presented a problem for casting directors. Despite a ‘closet filled with fashionable frocks to make me look as racially varied as an Eighties Benetton poster,’ she wrote in an essay for Elle, ‘I wasn’t black enough for the black roles and I wasn’t white enough for the white ones, leaving me somewhere in the middle as the ethnic chameleon who couldn’t book a job.’

Meghan Markle on the set of Deal Or No Deal.NBC/AFP/Getty Images

To make matters even more galling, Meghan did not feel that her producer boyfriend, Trevor Engelson whom she met when she was 23, was helping her get good parts. (He certainly didn’t in Remember Me, which he produced.) Engelson was a shaggy, genial, high-energy producer and talent manager with a baritone Long Island voice. He had hustled his way to the middle of Hollywood’s B-list and had his own management company. Nearly five years older than Meghan and included in The Hollywood Reporter’s “Next Gen 2009,” a list of up-and-comers ages thirty-five and under, he was used to being the one she needed for connections in the indus­try.

In the summer of 2010, when her agent got her a read for the new USA Network drama A Legal Mind (as Suits was initially titled), Meghan was beside herself. Rachel Zane was a dream role. Set in the gleaming glass offices of a fictional Manhattan law firm, the script by former banker Aaron Korsh was—for a change—snappy and sophisti­cated. The Rachel Zane character was a self-confident paralegal who exuded Upper East Side class and had enough edge to make her a cred­ible sparring partner of a cocky, boyish new associate attorney.

Casting director Bonnie Zane went through 150 auditions before she sent her top choices up to the Suits decision makers. One morning in January 2020, I sat in the Terrace Room of the Sunset Tower Hotel in West Hollywood and watched Meghan’s auditions for Rachel on Zane’s iPad. The clip shows Meghan in a youthful spaghetti-strap dress, less polished and more California than she is today. She is natural and freckly with too-shiny lip gloss, but she plays her Rachel lines with unpretentious poise. ‘I loved her,’ Bonnie says simply. “She was just an actor for hire,” she told me. " No reputation … I didn’t know Meghan because her résumé was Hot Girl [in an Ashton Kutcher movie].” Happily this was one audition where Meghan’s indeterminate ethnicity was an asset.

By the time of the Suits casting in 2010, issues surrounding mixed-race identity were beginning to bloom in the national consciousness. The New York Times noted in January 2011 that the latest crop of college students included the largest group of mixed-race people ever to come of age in the United States, a generation at the forefront of a demographic shift driven by immigration and intermarriage. Suddenly, after a long history of sparse roles for people of color, a fluid racial identity offered Hollywood cachet. Suits director Kevin Bray is biracial himself and was actively pushing for diversity on the show, while middlebrow USA Network was trying to upgrade from being what James Wolcott in Vanity Fair called “a spa resort for tired eyes.” “They wanted someone more street smart and urbane” for the Rachel part, Bray told me. “We didn’t want the trope of the bouncin’ and behavin’ Breck hair ad, slow-motion girls coming in … . As soon as she walked in, Meghan blew that trope up.” The zeitgeist had turned in Meghan’s direction at last.

Bray remembers: ‘Everyone to a man in the room said, “Where did she come from?” It was like group hypnosis.’ Meghan projected such an uptown aura you would never know that she had arrived at the audition in a rattling second-hand Ford Explorer that required her to climb in through the trunk, as her dwindling bank account would not allow her to get the broken door locks fixed. She got the call from her agent on August 24, 2010: Rachel was hers. It was validation after eight scrappy years.

In be­tween shooting the pilot in New York and the seismic news that the show had been greenlit for the next TV season, Trevor Engelson pro­posed to her on a romantic vacation in Belize. Suits required a five-year commitment to live in Toronto for nine months at a stretch of shooting. She signed on without hesitation. The first season debuted in June 2011 to strong reviews and pleasing attention. Shortly after it wrapped, Meghan married Trevor in a barefoot wedding in Ocho Rios, Jamaica.

The wedding earned a brief write-up in The Hollywood Reporter. The bride wore a simple white notch dress with a sparkling silver waistband. A planeload of entertainment indus­try friends came down for four days of partying on the white beach. The only jarring note, one wedding guest remembers, is that in the itinerary Meghan sent out was a note requesting “No social media, please.”

“We were all laughing because she had been on Suits for a few months at that point and we were like, is she kidding me?” the guest told me. “She was already like, ‘I’m a really big actress.’ " Afterward, the bride returned to Toronto and the groom to L.A. The new Mr. and Mrs. Trevor Engelson settled into a married life that would primarily be conducted on Skype.

Gabriel Macht as Harvey Specter and Meghan Markle as Rachel Zane in Suits.USA Network/Handout

Meghan was now earning around $50,000 an episode. Her Working Actress blog, that anonymous ballad of thwarted ambi­tion, had to find a new author. Meghan’s next online literary offering would be a stylishly designed lifestyle effort she called The Tig after her favorite full-bodied red wine, Tignanello. The Tig was an exfoliated, liberal-leaning world of undiscovered travel destinations, soft chats with “influencers” synonymous with Meghan’s upward trajectory, and women’s empow­erment causes where even victims looked their best. Plugs for cosmetics, travel destinations, restaurants and self-care products made The Tig a dragnet for luxury freebies. She won a reputation amongst the marketers of luxury brands of being warmly interested in receiving bags of designer swag.

The airbrushing of Meghan’s life had officially begun. One who swiftly found he didn’t fit the new picture was her husband, whose ca­reer was not on the upswing. For nearly two years, Trevor rearranged his life to spend sojourns working from Toronto, but Meghan rarely reciprocated. Trevor started to dread she was going to dump him. A friend tells me she remembers running into him at a wedding where he confided mournfully, “She’s not coming back anymore. We are not really talking that much. This is getting ridiculous. She’s in another country and we’re barely seeing each other. … [I have] this awful feeling she’s just going to become huge and leave me.”

One weekend when he came to see her in Toronto, Meghan told him she was out of love and it was over. Shortly after Meghan delivered the coup de grâce, a package arrived for Trevor by registered mail in Los Angeles. It contained his wife’s diamond en­gagement ring and her gold wedding band.

Had Suits been shot in New York as the producers and stars so ar­dently wanted, Meghan might have been swallowed up by a city unim­pressed by minor cable stars. In L.A., the entertainment world is sprawling yet insular. Thousands of Meghans churn through unre­marked. Toronto’s charm is that it’s both cosmopolitan and provincial. There’s a permeable elite that’s easy to navigate. Toronto resembles London in that the political, journalistic, and theatrical worlds all sit at the same table, but it’s profoundly different from London in its equable absence of snark. When Soho House, the London-based membership club for status cultivators, opened an outpost in 2012 in a three-story Georgian building known as the Bish­op’s Block, Toronto could officially claim a cool factor.

For an aspiring cosmopolite like Meghan, who had always felt oth­ered by her mixed race, the city’s ambience provided a heady cultural and social accelerant. Within a couple of years, she was hobnobbing with TV host Ben Mulroney and his style-queen wife, Jessica; the heartthrob crooner Michael Bublé; and an assortment of celebrity chefs and film and fash­ion floaters. As soon as Trevor was ushered out of the picture, she started dating, first linked to a hockey hunk named Michael Del Zotto and, for the two years before she met Harry, the golden-boy chef Cory Vitiello, who was named as one of Canada’s most beautiful people and whose restaurant, the Harbord Room was a hangout for le tout Toronto.

Now that she’d had her big break, Meghan was desperate to make Rachel Zane more than a support player in the Suits lineup. It was vexing that she was not listed higher on the call sheet, that all-important document in the world of film and TV production that’s sent out to the cast and crew as the strategy map for the next day’s shooting. The call sheet is more than a memo to actors stipulating what time and where each should show up. It’s also a status register, which makes the whole concept fraught.

The dream of every rising player is to be listed on the call sheet at number one, with all the perks that go with it—car and driver, your own trailer on location, the first consult on disruptive schedule changes, and generous expenses that include a sheaf of airline tickets for week­ends. For the seven years she performed on Suits, Meghan Markle was number six on the call sheet.

She quickly sensed the clout of the veteran TV character actor Rick Hoffman and convinced him to secure from the producers a car and driver for her, a bold move be­cause a chauffeured car is a much-desired perk allocated to players listed at number one and two.

Meghan was beloved by the show’s producers because she never said no to promotion. “Anytime we asked anything extra to be done, whether it was a fundraiser or glad-handing at the Television Critics Association event. … Meghan always said, ‘Sure, I’ll do it,’” In return, Meghan was able to make Suits executives powerful sounding boards. She sought advice on how to increase her part “without looking like it’s a land grab … and expand her role.”

While Meghan worked to enhance Rachel, Rachel also enhanced Meghan. Jolie Andre­atta’s polished wardrobe choices of tight pencil skirts that fit within an exhale, tastefully unbuttoned fitted white shirts, and sky-high nude heels were wrapped into Meghan’s psyche as much as her person. Pro­motional junket videos show her more confident and sleek with every performance.

The buzzed-up Jessica Mulroney was Meghan’s thirty-something role model in style and new BFF. Meghan has always been astute in flattering fashionable and famous women and absorbing their networks. Physically, Jessica could have been Meghan’s sister and was just as tireless. She had turned her private life into a permanent destination wedding, posting a ceaseless flow of images about her glossy existence. As a fashion stylist cum marketer, Jessica marked everything in her world with a hashtag. Her own three-day nuptials were covered on Canadian television news, her parenting became a partnership with Pampers, and her trips to the gym a promotional op­portunity for Adidas. It could not have escaped Meghan’s notice that a crucial factor in Jessica’s commercial leverage was her famous Mulroney hus­band. “The Brandtastic Life of Ben and Jessica” was the title of a To­ronto Life magazine puff piece on the Mulroneys.

Meghan Markle and Jessica Mulroney in 2016 in Toronto.George Pimentel/iStockPhoto / Getty Images

Meghan absorbed Jessica’s tactics like a sea sponge. But what sealed Meghan’s upward trajectory in Toronto was her alliance with the Canadian-born global membership director of Soho House, Markus Anderson, the chain’s global arbiter of who was—and wasn’t—worthy of the exalted status of “influencer.” Soho House was Meghan’s glide path into a newly porous and ag­gressively mobile world of shortcut social climbing. The blended affluence and social and attitudinal aesthetic of its “curated” membership defined Meghan’s relentlessly ambi­tious world. The rest of the Suits team were unaware of Meghan’s strenuous efforts to move upward. ‘You didn’t hear about it and she didn’t put it up front, but she’s playing three-dimensional chess with you,’ Kevin Bray told me.

By 2014, Meghan was famished for prestige, frantic for validation. Stars like Angelina Jolie, Cate Blanchette, and Nicole Kidman were UN goodwill ambassadors, travelling the world in their halos and talking about hunger and refugees. That should be her! The challenge was to break into the celebrity and humanitarian nexus that would spring her from the cable ghetto. It did not matter that her first foray—a One Young World panel at their fired-up 2014 leadership summit in Dublin about “the role media plays in the gender gap”—featured a less than stellar lineup of a YouTube makeup star, an Anheuser-Busch executive, and corporate suit from GE. At least it was a start.

To penetrate the United Na­tions, she pitched herself to learn more about its mission by shadowing Elizabeth Nyamayaro, senior adviser to the executive director of UN Women. Meghan had come to the right place. Nya­mayaro, a stunning forty-year-old Zimbabwean overachiever, was considered something of a piece of work herself, mowing down the stuffier old guard at the UN in the launch of a flashy, celebrity-heavy campaign called HeForShe whose mission was to co-opt men to advo­cate for women. It launched with a bang at the 2014 UN General As­sembly in New York with an address by UN goodwill ambassador Emma Watson (that netted over four million views on YouTube.)

Meghan was determined to be next and got her humanitarian break at the UN Women’s 2015 summit, marking the twentieth anniversary of the Fourth World Conference on Women in Beijing, where Hillary Clinton had first uttered the words “Women’s rights are human rights.” Behind that podium at the United Nations, wearing a serious black dress on International Women’s Day, Meghan kicked off her speech with dazzling aplomb. In all, it was a tour de force one might think would elevate her to the main stage at the World Eco­nomic Forum at Davos the next year.

Meghan Markle in Rwanda in 2017.P0009/The Associated Press

And yet … the traction after that day was minimal. She did an enthusiastic interview about a UN Women trip to Rwanda with Larry King, but by then he had lost his CNN show. It was on a digital channel and he seemed half-asleep. Meghan was always so close to fame, but never quite there: basic cable, not premium cable; inside the magazines but not on the cover. A UN advocate but not a UN ambassador, a local celebrity in Toronto but an unknown in New York. As she filmed the fifth and sixth seasons of Suits, she was well aware of the clock running down. She was about to turn thirty-five and still had not gotten the call from Anna Wintour to join the red carpet at the Met Gala.

Meghan’s love life was equally trapped in a cul-de-sac. In 2016, Cory Vitiello, with whom she and her dogs had recently moved in, clearly had no plans to marry any time soon. Meghan’s sights once again turned to London. It was the height of the 2016 summer season. Princess Diana used to love this time of year, with the influx of what she called the “July Americans” in town. Meghan’s reps scored her a stylish invitation to wear Ralph Lauren clothes in a celebrity box at Wimbledon, where Serena Williams was playing. Markus Anderson ginned up a discount room for Meghan at her favorite Soho House, the Dean Street Townhouse. She hit the Lon­don scene in June with glamor guns blazing.

One stop was a charity dinner hosted by Phones 4u billionaire John Caudwell at his Mayfair mansion where Meghan confided to Lizzie Cundy, host of an obscure reality show titled So Would You Dump Me Now?, that she’d love to move to London and have a celebrity boyfriend.

Meghan pushed ever onward to a strategic drink at the Scarsdale Tavern in Kensington with former tabloid editor Piers Morgan. After a successful run in L.A. and a less successful attempt to fill Larry King’s shoes on CNN, Piers had returned to London, hungry for the rude, punchy ebullience of his tabloid days of the nineties. He now had a new vehicle (and massive Twitter following) in ITV’s Good Morning Britain. He often tweeted about Suits, of which he happened to be a fan, and struck up a social media friendship with Meghan. “I’m in London for a week of meetings and Wimbledon,” she DM’d him. “Would love to say Hi!”

It was a cor blimey moment for all the men propping up the bar when she walked into the Kensington pub for her charm offensive. “She looked every inch the Hollywood superstar,” wrote Piers in a 2017 column in the Daily Mail, “very slim, very leggy, very elegant, and impossibly glamorous. She was even wearing the obligatory big black shades beloved of LA thes­pians.” He was impressed with her undisguised ambition.

But it was thanks to Violet von Westenholz, who had issued Meghan the Wimbledon invitation from Ralph Lauren, that the cards fell into place. As the daughter of one of Prince Charles’s best friends, Violet knew everybody. Her sister Victoria had been romantically linked with Harry. When Meghan once again dangled the bait that she was looking for a boyfriend, Violet suggested an idea that was too good to be true. How to make it happen? Markus, of course. No one knew better than he about choreographing high-end social collisions.

Meghan’s UK agent Gina Nelthorpe-Cowne had lunch with her at London’s Delaunay restaurant on July 1, 2016, and thought her client had never looked more beautiful. Meghan, unable to contain her excitement, shared the secret of whom she was going to meet that night for drinks at Soho House. “There’s no way he’s going to be able to resist her,” Cowne thought.

Excerpted from The Palace Papers by Tina Brown Copyright © 2022 Tina Brown. Published byDoubleday Canada, a division of Penguin Random House Canada Limited. Reproduced by arrangement with the Publisher. All rights reserved.

Expand your mind and build your reading list with the Books newsletter. Sign up today.