Playboy Earl’s Son Stuns High Society With Engagement to Billionaire Heiress — Just Five Years After His Split From 72-Year-Old Hollywood Star
It’s the kind of plot twist even a tabloid editor wouldn’t dare invent.
Garrett Moore — society party king, son of the Earl of Drogheda, and a man once engaged to a Hollywood icon nearly twice his age — has announced a new engagement that is sending shockwaves from London to Manhattan.
This time, his bride-to-be is Hope Chilton, the elegant 25-year-old daughter of American billionaire investor Richard Lockwood Chilton Jr.
And yes — the age gap headlines have already begun writing themselves.
At 39, Moore is no stranger to public fascination. His events have entertained supermodels, rockstars, and royalty. His former engagement to actress Colleen Camp, now 72, was a society spectacle of its own. But this new romance marks a dramatic pivot — one that has catapulted him from eccentric London playboy to future member of one of America’s most powerful financial dynasties.
From Drama to Dynasty: A Relationship Rewrite
Moore’s engagement to Camp in 2020 stunned both Hollywood and the British aristocracy. Camp, known for Apocalypse Now, Police Academy, and Clue, later dismissed the relationship with her famously sharp humour:
“A joke that went too far.”
The pair broke things off the same year — and Moore retreated from the spotlight.
Now, insiders say the match with Hope represents something entirely different.
“She’s warm, brilliant, grounded — and they’re incredible together,” a family friend revealed. “Both families couldn’t be happier.”
For a man once defined by flamboyant parties and tabloid curiosity, this engagement feels less like a headline grab… and more like a long-awaited landing.
Who Is Hope Chilton? The Billionaire Daughter Joining London’s Aristocratic Map
Hope Chilton grew up in Darien, Connecticut, attended the prestigious Greenwich Academy, and later studied criminal science at UNC.
She is the daughter of hedge-fund titan Richard L. Chilton Jr, founder of Chilton Investment Company, which has managed billions of dollars across global markets.
Her father’s net worth is estimated at $1.3 billion — with art museum board seats, luxury properties, and deep philanthropic ties shaping the family’s public identity.
Hope’s mother is equally influential, active across charity boards in arts and education.
If Moore once lived on the edges of high society, he’s now right in the centre of it.
A Match Made in Mayfair (and Manhattan)
The pair reportedly met through businessman Robin Birley, the powerhouse behind London’s elite clubs such as 5 Hertford Street. Moore has long been part of Birley’s inner social orbit, organizing high-glamour events for Louis Vuitton, Chanel, and global A-listers.
Hope, meanwhile, worked with Birley on membership operations at Maxime’s in New York — a crossover of worlds that brought the future couple face to face.
The connection was instant.
The relationship, quiet at first, gradually blossomed into something serious — culminating in the surprise engagement announcement now sending society tongues wagging.
The Wedding Everyone Already Knows Will Be a Spectacle
Although no date has been set, insiders say the ceremony is expected to be “extraordinary” — a union of:
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British nobility
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American billionaire wealth
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and two of the world’s most photographed social circles
If Garrett’s party-planning résumé is any indication, invitations will be gold-edged, champagne will pour freely, and the guest list will be a surreal blend of aristocrats, Hollywood names, hedge-fund moguls, and fashion royalty.
A Family Lineage Written in Cameras, Power, and Prestige
Garrett Moore’s own family tree is nothing short of iconic.
His father, Derry Moore, the 12th Earl of Drogheda, is one of the most celebrated portrait photographers of his generation, having photographed:
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Princess Diana
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William and Harry
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Ronald Reagan
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David Bowie
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Mahatma Gandhi
His work hangs across the National Portrait Gallery, and he has published more than 30 books.
Garrett’s mother, Alexandra Henderson, built her own legacy at the BBC as a producer and editor.
With Hope’s billionaire lineage and Garrett’s aristocratic and artistic heritage, their marriage unites two worlds rarely seen on the same page — unless it’s the front page.
From Hollywood Scandal… to High-Society Power Couple
Once known for glamorous chaos, dramatic headlines, and unconventional romances, Garrett Moore is now stepping into a new identity:
Fiancé. Future son-in-law to a billionaire.
Heir to a noble title.
Architect of one of the most anticipated society weddings of the decade.
Whatever comes next, one thing is certain:
London high society will be watching.
New York high society will be watching.
And the rest of the world will be watching too — because this “perfect match” may be the most fascinating one yet.