Prince Harry and Meghan Markle, the Duke and Duchess of Sussex, have been playing a game of royal tug-of-war with the British monarchy for years now.

Stepping back as senior royals might have seemed like a liberating move, but freedom comes with its own set of golden handcuffs. Since then Harry has been making one misstep after another in his quest to carve out a new life with Meghan while simultaneously airing family laundry in public. But perhaps Harry’s “greatest mistake,” according to royal expert Katie Nicholl, can be traced back to the very beginning of his relationship with Meghan.

In their official engagement photos from November 2017, Nicholl notes that Harry appeared overly protective and defensive of his then-fiancée after keeping their relationship and her presence in his life a secret for very long.

“It’s like he’s making that physical connection. He’s presenting her to the world for the first time, because he’d kept her in secret. I still think one of his greatest mistakes was never introducing her to us, the press, and allowing that connection to be forged. It’s like, ‘She’s mine. I’m presenting you to her, but hands off. “

This possessive stance, she not-so-subtly suggests, may have set the tone for the couple’s rocky relationship with the royal family and the treatment Meghan has received at the hands of the paparazzi, the fans of Prince William and Kate Middleton, and every person online willing to indulge in gossip. In a way, it is being suggested that Harry’s decision to not put his budding relationship with Meghan through media scrutiny in its initial phases since he knew that she would face discrimination and ridicule for not being of royal heritage was a mistake that set the tone of how the Duchess of Sussex will be treated out in the world, now and forever.

A seemingly benign coincidence of Meghan’s products getting some promotion the very day Kate broke her isolation to appear at the Trooping Colors with only a few hours of notice got the Suits star criticized for trying to “upstage” the ailing the Princess.

Harry’s prioritization of Meghan over his royal duties and family ties has had far-reaching consequences. Fast forward to 2024, and the couple’s decision to move to California has only widened the rift. Rumors swirl that Harry is feeling the weight of his family’s rejection, with some even suggesting that Meghan is concerned for her husband’s mental well-being.

Prince William, once a close confidant and ally, is said to be angry and hurt by his brother’s actions. Reports suggest that William holds more sway over royal decisions than King Charles and has already decided his brother’s fate. Moreover, the fact that Charles has offered Frogmore Cottage, Harry and Meghan’s former home in England, to Prince Andrew sends a clear message that even the black sheep of the family is more worthy of a royal roof over his head than his own son and daughter-in-law.

To add insult to injury, Meghan’s attempts to rub elbows with the A-listers have also hit a few snags, like her personal letter to Taylor Swift, asking the pop princess to grace her podcast Archetypes with her presence, was met with a resounding “thanks, but no thanks.” But this one loss has been phrased as a brutal loss that somehow describes the status of her whole life in California. As the Daily Mail writes:

“They thought when they moved to California, ‘we’ll be at the centre of this sort of royal court and everyone will come to see us.’ But it never seems to be working out like that.”

At the end of the day, Harry’s love for Meghan is undeniable, but there might just be some truth in what Nicholl says. There is a high probability that the U.K. tabloids would have still bashed Meghan after their Royal demotion, but in trying to initially shield her from the media and Royal scrutiny that hounded Princess Diana all her life, Harry may have alienated her in ways he didn’t even comprehend.