November 23, 2025 • 14 mins
In the late 1990s, a socialite named Ghislaine Maxwell introduced Andrew to Jeffrey Epstein. What began as friendship eventually became a public relations nightmare. As Epstein’s crimes came to light, photographs of Andrew ignited global outrage.
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Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!
Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!
We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com
Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
This is Crown and Controversy, an entertainment series inspired by
true events inside the modern British monarchy. While no one
truly knows what happens behind closed palace doors, this story
draws from public records, news reports, and on the record quotes.
Some scenes have been dramatized for a storytelling effect Calaroga
(00:24):
Shark media.
Speaker 2 (00:46):
There are photographs that do not fade. They live in archives,
in documentaries. In the quiet pause before a statement, three
particular images would come to define a royal crisis and
a personal downfall. The first is said to have been
taken in a London flat. A young woman, Virginia Gufre,
(01:07):
then known as Virginia Roberts, smiles faintly next to her,
A man with a familiar face, relaxed, confident, unaware that
the moment would outlive him. Behind them, Guilaine Maxwell, half
in shadow. The image surfaced in early twenty eleven and
became one of the most widely circulated royal photographs of
(01:29):
the modern era. Andrew said he had no recollection of
ever meeting the young woman and denied all allegations connected
to her. Still, the picture became a symbol that the
palace could not contain. The second image shows a walk
through Central Park in the winter of twenty ten. Andrew,
(01:50):
wearing a coat and scarf, is beside Jeffrey Epstein, the
American financier who had been convicted two years earlier of
sex offenses involving a miner. The meeting came after Epstein's
first release from jail. Andrew would later say that he
went to New York to end the friendship. The world
was not persuaded. The third photograph shows the doorway of
(02:14):
Epstein's Manhattan townhouse. The Prince stands there smiling as a
member of staff closes the door behind him. That photograph,
taken during the same trip, would appear in newspapers around
the world and come to represent what many believed was
the tone of the entire scandal, careless, privileged and entirely
(02:36):
out of touch. Before the photographs, there had been private dinners, introductions,
and meetings arranged quietly. After them, there were headlines that
did not stop a royal household scrambling to manage a crisis,
and the slow realization that a friendship, once tolerated, had
become a national embarrassment. This is Crown and controversy Prince
(03:00):
Andrew Episode four, The Epstein Connection. In the late nineteen nineties,
London society often mixed with New York wealth. Among the
guests who floated easily between those worlds was Geelane Maxwell,
daughter of the late publisher Robert Maxwell. She was known
(03:22):
for her charm, her confidence, and her access. Around that time,
she reportedly introduced Prince Andrew to Jeffrey Epstein. Epstein was,
by all appearances the kind of man a trade envoy
might wish to know. He owned private jets and properties
from Palm Beach to Paris. His connections extended from Wall
(03:43):
Street to the White House. He moved through social circles
that prized influence, and he understood that a photograph with
a royal could open doors far faster than a handshake
with a minister. Andrew, recently retired from the Royal Navy,
had been a tented Britain's Special Representative for Trade and Investment.
(04:03):
The job was not glamorous, but it gave him purpose.
He traveled constantly promoting British industry, attending conferences and shaking
hands with world leaders. Epstein's circle seemed like an efficient
shortcut to the kind of people who could invest in Britain.
For a time, the friendship seemed useful. The two men
(04:25):
appeared at events together, dined in London and New York,
and were often photographed with wealthy acquaintances. The relationship drew
little attention at first. Epstein was a financier with money
to spend, and Andrew was a prince who had always
been comfortable among the powerful. Inside Buckingham Palace, courtiers noticed
(04:47):
the names appearing beside Andrew's in the social pages. Some
of them carried reputations that raised quiet concern, yet few
believed it would lead anywhere dangerous. After all, Andrew had
long been considered the Queen's favorite son. To question him
too forcefully would have been to question her judgment. Then,
(05:09):
in December twenty ten, came the walk in Central Park.
Epstein had already served time in Florida after pleading guilty
to offenses involving a minor. His conviction was public record.
When photographers captured Andrew walking beside him in New York.
The images ignited immediate outrage. The timing seemed impossible to defend.
(05:33):
Andrew's office said little. The palace, too, remained silent. Within days,
the photographs appeared across front pages on both sides of
the Atlantic. Commentators speculated about how long the friendship had
continued and why Andrew had chosen to visit Epstein at all.
Andrew would later explain that he went to New York
(05:53):
only to end the relationship, Yet his decision to stay
at Epstein's home for several days undercut the story. Witnesses
recalled dinner parties and meetings during that visit. The image
of a royal staying with a convicted sex offender was catastrophic.
The Queen was reportedly distressed, Charles, already preparing for his
(06:16):
future as king, urged caution. William watched and learned how
swiftly one man's poor judgment could threaten the dignity of
the institution itself. The Queen's affection could not erase the storm.
(06:44):
By early twenty eleven, the headlines had hardened into something permanent.
Newspapers printed the photograph taken years earlier in the London flat.
The young woman at the center of the image identified
herself publicly Andrew meeting her. The denials did not matter.
The public had the picture. Around this time, pressure built
(07:08):
on the government to review Andrew's role as trade envoy.
Officials received quiet messages from diplomats who said the Prince's
name was being met with raised eyebrows at meetings abroad.
The Foreign Office found itself defending an arrangement that had
once seemed harmless. There were reports of extravagant travel. Journalists
(07:31):
calculated flight patterns and hotel stays, pointing to a preference
for private jets and expensive delegations. The nickname air Miles Andy,
once a tabloid joke, returned with a new edge in private.
Andrew's team insisted the trips were legitimate. He had helped
British firms win contracts. They said he had promoted innovation
(07:54):
and goodwill, but perception mattered more than paperwork. The friendship
with Epstein coloured everything that came after. Diplomats whispered that
the Duke spoke with more confidence than discretion. One account
from an overseas reception described him as outspoken to the
point of rudeness. Another described an entourage that seemed unusually
(08:17):
large for a man who claimed to work without pay.
There was even amusement later retold by former embassy staff,
about a personal valet traveling with an ironing board that
followed Andrew everywhere. The anecdotes became symbols of tone deaf excess.
They confirmed what many already believed that the Duke had
(08:38):
lost touch with public expectation. Then came a new embarrassment.
Sarah Ferguson, Andrew's ex wife but longtime companion, admitted that
she had accepted fifteen thousand pounds from Jeffrey Epstein to
help settle her debts. She called it a gigantic error.
The revelation compounded the crisis. What had begun as a
(09:02):
friendship now reached into every corner of Andrew's life. The
Queen remained outwardly calm. Behind the scenes, courtiers described a
sovereign torn between maternal instinct and constitutional duty. Her son's
behavior was not criminal, but it was indefensible for a
monarch who valued discretion above all else. The headlines were intolerable.
(09:26):
The Palace confirmed that Andrew would step down as Britain's
trade envoy. The announcement was short and stripped of emotion.
Inside Whitehall, relief was palpable. The scandal had embarrassed ministries
from London to Washington. Andrew was said to be angry.
He believed he had served well and unfairly become the
(09:47):
target of gossip. To the public. It looked like consequence
at last, for a brief period, he retreated from view.
The news cycle moved on, but scandals have long half lives,
and the next wave would be worse. In twenty fifteen,
(10:15):
new court filings in the United States again referenced Andrew's name.
The same photograph reappeared, reprinted endlessly. Commentators debated what it meant,
what could be proven, what was speculation. Each repetition deepened
the damage. In twenty nineteen, Jeffrey Epstein was arrested again,
this time on federal charges of sex trafficking miners. He
(10:40):
was found dead in his jail cell weeks later, in
what authorities ruled a suicide. That same year, renewed focus
turned to Ghislaine Maxwell, who would later be convicted in
the United States of conspiring to recruit and groom victims
for Epstein's abuse. She is serving a lengthy sentence. Today.
(11:00):
Andrew was not charged with any crime, but he was
again in every headline. Each new revelation in the United
States reignited questions. In Britain, charities began to distance themselves.
Military units quietly sought reassignment of their royal patronages. Public
support evaporated. In early twenty twenty two, Virginia Juffrey filed
(11:25):
a civil lawsuit against Andrew in New York. The case
was settled that February. The settlement included no admission of wrongdoing,
but the damage was complete. After that, the process of
separation between the Duke and the institution accelerated. Honorary military
roles were removed, public appearances were curtailed, invitations dried up.
(11:47):
The Palace phrased its statements in language that balanced compassion
with finality. Throughout Andrew maintained his innocence. He continued to
deny all allegations, insisting that the truth would vindicate him,
but in the court of public opinion, verdicts rarely wait
for evidence. Within the family, the response was quiet but decisive.
(12:10):
The Queen, ever loyal to her children, reportedly continued to
offer private support. Charles, who would soon become king, believed
that the monarchy could not afford sentiment. William, now watching
the machinery of consequence up close, understood that the survival
of the institution would always outweigh personal ties. Three images
(12:33):
remained at the center of it all. The London flat,
the New York Park, the Manhattan doorway. They were not
proof of guilt, but they were evidence of judgment, or
the lack of it. For the monarchy, the lesson was
sharp and enduring. Reputation is inheritance. Once lost, it cannot
(12:54):
be reclaimed. The Queen lived her entire reign by the
idea that the crown must be seen to endure. In
the end, it did. The cost was a sun next time,
a single interview meant to clear the air, instead destroys
what little remained. While no one truly knows what happens
(13:30):
behind closed palace doors.
Speaker 1 (13:32):
This entertainment series uses news sources, on the record, quotes,
and some artistic license. Some moments have been dramatized for
storytelling effect. To keep up with the modern day Royal family,
follow our sister podcast, Palace Intrigue, a seven day a week,
(13:53):
ten minute update on the Royals, Crown and Controversy, is
a production of Caloroga Shark Meets Executive producers Mark Francis
and John McDermott
This is Crown and Controversy, an entertainment series inspired by
true events inside the modern British monarchy. While no one
truly knows what happens behind closed palace doors, this story
draws from public records, news reports, and on the record quotes.
Some scenes have been dramatized for a storytelling effect Calaroga
(00:24):
Shark media.
Speaker 2 (00:46):
There are photographs that do not fade. They live in archives,
in documentaries. In the quiet pause before a statement, three
particular images would come to define a royal crisis and
a personal downfall. The first is said to have been
taken in a London flat. A young woman, Virginia Gufre,
(01:07):
then known as Virginia Roberts, smiles faintly next to her,
A man with a familiar face, relaxed, confident, unaware that
the moment would outlive him. Behind them, Guilaine Maxwell, half
in shadow. The image surfaced in early twenty eleven and
became one of the most widely circulated royal photographs of
(01:29):
the modern era. Andrew said he had no recollection of
ever meeting the young woman and denied all allegations connected
to her. Still, the picture became a symbol that the
palace could not contain. The second image shows a walk
through Central Park in the winter of twenty ten. Andrew,
(01:50):
wearing a coat and scarf, is beside Jeffrey Epstein, the
American financier who had been convicted two years earlier of
sex offenses involving a miner. The meeting came after Epstein's
first release from jail. Andrew would later say that he
went to New York to end the friendship. The world
was not persuaded. The third photograph shows the doorway of
(02:14):
Epstein's Manhattan townhouse. The Prince stands there smiling as a
member of staff closes the door behind him. That photograph,
taken during the same trip, would appear in newspapers around
the world and come to represent what many believed was
the tone of the entire scandal, careless, privileged and entirely
(02:36):
out of touch. Before the photographs, there had been private dinners, introductions,
and meetings arranged quietly. After them, there were headlines that
did not stop a royal household scrambling to manage a crisis,
and the slow realization that a friendship, once tolerated, had
become a national embarrassment. This is Crown and controversy Prince
(03:00):
Andrew Episode four, The Epstein Connection. In the late nineteen nineties,
London society often mixed with New York wealth. Among the
guests who floated easily between those worlds was Geelane Maxwell,
daughter of the late publisher Robert Maxwell. She was known
(03:22):
for her charm, her confidence, and her access. Around that time,
she reportedly introduced Prince Andrew to Jeffrey Epstein. Epstein was,
by all appearances the kind of man a trade envoy
might wish to know. He owned private jets and properties
from Palm Beach to Paris. His connections extended from Wall
(03:43):
Street to the White House. He moved through social circles
that prized influence, and he understood that a photograph with
a royal could open doors far faster than a handshake
with a minister. Andrew, recently retired from the Royal Navy,
had been a tented Britain's Special Representative for Trade and Investment.
(04:03):
The job was not glamorous, but it gave him purpose.
He traveled constantly promoting British industry, attending conferences and shaking
hands with world leaders. Epstein's circle seemed like an efficient
shortcut to the kind of people who could invest in Britain.
For a time, the friendship seemed useful. The two men
(04:25):
appeared at events together, dined in London and New York,
and were often photographed with wealthy acquaintances. The relationship drew
little attention at first. Epstein was a financier with money
to spend, and Andrew was a prince who had always
been comfortable among the powerful. Inside Buckingham Palace, courtiers noticed
(04:47):
the names appearing beside Andrew's in the social pages. Some
of them carried reputations that raised quiet concern, yet few
believed it would lead anywhere dangerous. After all, Andrew had
long been considered the Queen's favorite son. To question him
too forcefully would have been to question her judgment. Then,
(05:09):
in December twenty ten, came the walk in Central Park.
Epstein had already served time in Florida after pleading guilty
to offenses involving a minor. His conviction was public record.
When photographers captured Andrew walking beside him in New York.
The images ignited immediate outrage. The timing seemed impossible to defend.
(05:33):
Andrew's office said little. The palace, too, remained silent. Within days,
the photographs appeared across front pages on both sides of
the Atlantic. Commentators speculated about how long the friendship had
continued and why Andrew had chosen to visit Epstein at all.
Andrew would later explain that he went to New York
(05:53):
only to end the relationship, Yet his decision to stay
at Epstein's home for several days undercut the story. Witnesses
recalled dinner parties and meetings during that visit. The image
of a royal staying with a convicted sex offender was catastrophic.
The Queen was reportedly distressed, Charles, already preparing for his
(06:16):
future as king, urged caution. William watched and learned how
swiftly one man's poor judgment could threaten the dignity of
the institution itself. The Queen's affection could not erase the storm.
(06:44):
By early twenty eleven, the headlines had hardened into something permanent.
Newspapers printed the photograph taken years earlier in the London flat.
The young woman at the center of the image identified
herself publicly Andrew meeting her. The denials did not matter.
The public had the picture. Around this time, pressure built
(07:08):
on the government to review Andrew's role as trade envoy.
Officials received quiet messages from diplomats who said the Prince's
name was being met with raised eyebrows at meetings abroad.
The Foreign Office found itself defending an arrangement that had
once seemed harmless. There were reports of extravagant travel. Journalists
(07:31):
calculated flight patterns and hotel stays, pointing to a preference
for private jets and expensive delegations. The nickname air Miles Andy,
once a tabloid joke, returned with a new edge in private.
Andrew's team insisted the trips were legitimate. He had helped
British firms win contracts. They said he had promoted innovation
(07:54):
and goodwill, but perception mattered more than paperwork. The friendship
with Epstein coloured everything that came after. Diplomats whispered that
the Duke spoke with more confidence than discretion. One account
from an overseas reception described him as outspoken to the
point of rudeness. Another described an entourage that seemed unusually
(08:17):
large for a man who claimed to work without pay.
There was even amusement later retold by former embassy staff,
about a personal valet traveling with an ironing board that
followed Andrew everywhere. The anecdotes became symbols of tone deaf excess.
They confirmed what many already believed that the Duke had
(08:38):
lost touch with public expectation. Then came a new embarrassment.
Sarah Ferguson, Andrew's ex wife but longtime companion, admitted that
she had accepted fifteen thousand pounds from Jeffrey Epstein to
help settle her debts. She called it a gigantic error.
The revelation compounded the crisis. What had begun as a
(09:02):
friendship now reached into every corner of Andrew's life. The
Queen remained outwardly calm. Behind the scenes, courtiers described a
sovereign torn between maternal instinct and constitutional duty. Her son's
behavior was not criminal, but it was indefensible for a
monarch who valued discretion above all else. The headlines were intolerable.
(09:26):
The Palace confirmed that Andrew would step down as Britain's
trade envoy. The announcement was short and stripped of emotion.
Inside Whitehall, relief was palpable. The scandal had embarrassed ministries
from London to Washington. Andrew was said to be angry.
He believed he had served well and unfairly become the
(09:47):
target of gossip. To the public. It looked like consequence
at last, for a brief period, he retreated from view.
The news cycle moved on, but scandals have long half lives,
and the next wave would be worse. In twenty fifteen,
(10:15):
new court filings in the United States again referenced Andrew's name.
The same photograph reappeared, reprinted endlessly. Commentators debated what it meant,
what could be proven, what was speculation. Each repetition deepened
the damage. In twenty nineteen, Jeffrey Epstein was arrested again,
this time on federal charges of sex trafficking miners. He
(10:40):
was found dead in his jail cell weeks later, in
what authorities ruled a suicide. That same year, renewed focus
turned to Ghislaine Maxwell, who would later be convicted in
the United States of conspiring to recruit and groom victims
for Epstein's abuse. She is serving a lengthy sentence. Today.
(11:00):
Andrew was not charged with any crime, but he was
again in every headline. Each new revelation in the United
States reignited questions. In Britain, charities began to distance themselves.
Military units quietly sought reassignment of their royal patronages. Public
support evaporated. In early twenty twenty two, Virginia Juffrey filed
(11:25):
a civil lawsuit against Andrew in New York. The case
was settled that February. The settlement included no admission of wrongdoing,
but the damage was complete. After that, the process of
separation between the Duke and the institution accelerated. Honorary military
roles were removed, public appearances were curtailed, invitations dried up.
(11:47):
The Palace phrased its statements in language that balanced compassion
with finality. Throughout Andrew maintained his innocence. He continued to
deny all allegations, insisting that the truth would vindicate him,
but in the court of public opinion, verdicts rarely wait
for evidence. Within the family, the response was quiet but decisive.
(12:10):
The Queen, ever loyal to her children, reportedly continued to
offer private support. Charles, who would soon become king, believed
that the monarchy could not afford sentiment. William, now watching
the machinery of consequence up close, understood that the survival
of the institution would always outweigh personal ties. Three images
(12:33):
remained at the center of it all. The London flat,
the New York Park, the Manhattan doorway. They were not
proof of guilt, but they were evidence of judgment, or
the lack of it. For the monarchy, the lesson was
sharp and enduring. Reputation is inheritance. Once lost, it cannot
(12:54):
be reclaimed. The Queen lived her entire reign by the
idea that the crown must be seen to endure. In
the end, it did. The cost was a sun next time,
a single interview meant to clear the air, instead destroys
what little remained. While no one truly knows what happens
(13:30):
behind closed palace doors.
Speaker 1 (13:32):
This entertainment series uses news sources, on the record, quotes,
and some artistic license. Some moments have been dramatized for
storytelling effect. To keep up with the modern day Royal family,
follow our sister podcast, Palace Intrigue, a seven day a week,
(13:53):
ten minute update on the Royals, Crown and Controversy, is
a production of Caloroga Shark Meets Executive producers Mark Francis
and John McDermott
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