Jan. 9, 2026
Crown and Controversy - Prince Andrew - 4. The Epstein Connection
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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This is Crown and Controversy, an entertainment series inspired by
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true events inside the modern British monarchy. While no one
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truly knows what happens behind closed palace doors, this story
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draws from public records, news reports, and on the record quotes.
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Some scenes have been dramatized for a storytelling effect Calaroga
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Shark media.
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There are photographs that do not fade. They live in archives,
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in documentaries. In the quiet pause before a statement, three
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particular images would come to define a royal crisis and
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a personal downfall. The first is said to have been
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taken in a London flat. A young woman, Virginia Gufre,
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then known as Virginia Roberts, smiles faintly next to her,
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A man with a familiar face, relaxed, confident, unaware that
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the moment would outlive him. Behind them, Guilaine Maxwell, half
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in shadow. The image surfaced in early twenty eleven and
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became one of the most widely circulated royal photographs of
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the modern era. Andrew said he had no recollection of
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ever meeting the young woman and denied all allegations connected
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to her. Still, the picture became a symbol that the
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palace could not contain. The second image shows a walk
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through Central Park in the winter of twenty ten. Andrew,
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wearing a coat and scarf, is beside Jeffrey Epstein, the
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American financier who had been convicted two years earlier of
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sex offenses involving a miner. The meeting came after Epstein's
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first release from jail. Andrew would later say that he
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went to New York to end the friendship. The world
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was not persuaded. The third photograph shows the doorway of
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Epstein's Manhattan townhouse. The Prince stands there smiling as a
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member of staff closes the door behind him. That photograph,
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taken during the same trip, would appear in newspapers around
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the world and come to represent what many believed was
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the tone of the entire scandal, careless, privileged and entirely
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out of touch. Before the photographs, there had been private dinners, introductions,
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and meetings arranged quietly. After them, there were headlines that
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did not stop a royal household scrambling to manage a crisis,
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and the slow realization that a friendship, once tolerated, had
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become a national embarrassment. This is Crown and controversy Prince
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Andrew Episode four, The Epstein Connection. In the late nineteen nineties,
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London society often mixed with New York wealth. Among the
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guests who floated easily between those worlds was Geelane Maxwell,
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daughter of the late publisher Robert Maxwell. She was known
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for her charm, her confidence, and her access. Around that time,
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she reportedly introduced Prince Andrew to Jeffrey Epstein. Epstein was,
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by all appearances the kind of man a trade envoy
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might wish to know. He owned private jets and properties
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from Palm Beach to Paris. His connections extended from Wall
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Street to the White House. He moved through social circles
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that prized influence, and he understood that a photograph with
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a royal could open doors far faster than a handshake
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with a minister. Andrew, recently retired from the Royal Navy,
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had been a tented Britain's Special Representative for Trade and Investment.
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The job was not glamorous, but it gave him purpose.
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He traveled constantly promoting British industry, attending conferences and shaking
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hands with world leaders. Epstein's circle seemed like an efficient
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shortcut to the kind of people who could invest in Britain.
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For a time, the friendship seemed useful. The two men
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appeared at events together, dined in London and New York,
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and were often photographed with wealthy acquaintances. The relationship drew
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little attention at first. Epstein was a financier with money
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to spend, and Andrew was a prince who had always
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been comfortable among the powerful. Inside Buckingham Palace, courtiers noticed
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the names appearing beside Andrew's in the social pages. Some
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of them carried reputations that raised quiet concern, yet few
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believed it would lead anywhere dangerous. After all, Andrew had
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long been considered the Queen's favorite son. To question him
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too forcefully would have been to question her judgment. Then,
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in December twenty ten, came the walk in Central Park.
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Epstein had already served time in Florida after pleading guilty
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to offenses involving a minor. His conviction was public record.
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When photographers captured Andrew walking beside him in New York.
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The images ignited immediate outrage. The timing seemed impossible to defend.
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Andrew's office said little. The palace, too, remained silent. Within days,
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the photographs appeared across front pages on both sides of
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the Atlantic. Commentators speculated about how long the friendship had
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continued and why Andrew had chosen to visit Epstein at all.
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Andrew would later explain that he went to New York
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only to end the relationship, Yet his decision to stay
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at Epstein's home for several days undercut the story. Witnesses
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recalled dinner parties and meetings during that visit. The image
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of a royal staying with a convicted sex offender was catastrophic.
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The Queen was reportedly distressed, Charles, already preparing for his
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future as king, urged caution. William watched and learned how
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swiftly one man's poor judgment could threaten the dignity of
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the institution itself. The Queen's affection could not erase the storm.
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By early twenty eleven, the headlines had hardened into something permanent.
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Newspapers printed the photograph taken years earlier in the London flat.
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The young woman at the center of the image identified
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herself publicly Andrew meeting her. The denials did not matter.
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The public had the picture. Around this time, pressure built
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on the government to review Andrew's role as trade envoy.
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Officials received quiet messages from diplomats who said the Prince's
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name was being met with raised eyebrows at meetings abroad.
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The Foreign Office found itself defending an arrangement that had
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once seemed harmless. There were reports of extravagant travel. Journalists
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calculated flight patterns and hotel stays, pointing to a preference
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for private jets and expensive delegations. The nickname air Miles Andy,
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once a tabloid joke, returned with a new edge in private.
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Andrew's team insisted the trips were legitimate. He had helped
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British firms win contracts. They said he had promoted innovation
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and goodwill, but perception mattered more than paperwork. The friendship
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with Epstein coloured everything that came after. Diplomats whispered that
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the Duke spoke with more confidence than discretion. One account
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from an overseas reception described him as outspoken to the
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point of rudeness. Another described an entourage that seemed unusually
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large for a man who claimed to work without pay.
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There was even amusement later retold by former embassy staff,
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about a personal valet traveling with an ironing board that
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followed Andrew everywhere. The anecdotes became symbols of tone deaf excess.
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They confirmed what many already believed that the Duke had
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lost touch with public expectation. Then came a new embarrassment.
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Sarah Ferguson, Andrew's ex wife but longtime companion, admitted that
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she had accepted fifteen thousand pounds from Jeffrey Epstein to
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help settle her debts. She called it a gigantic error.
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The revelation compounded the crisis. What had begun as a
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friendship now reached into every corner of Andrew's life. The
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Queen remained outwardly calm. Behind the scenes, courtiers described a
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sovereign torn between maternal instinct and constitutional duty. Her son's
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behavior was not criminal, but it was indefensible for a
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monarch who valued discretion above all else. The headlines were intolerable.
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The Palace confirmed that Andrew would step down as Britain's
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trade envoy. The announcement was short and stripped of emotion.
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Inside Whitehall, relief was palpable. The scandal had embarrassed ministries
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from London to Washington. Andrew was said to be angry.
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He believed he had served well and unfairly become the
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target of gossip. To the public. It looked like consequence
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at last, for a brief period, he retreated from view.
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The news cycle moved on, but scandals have long half lives,
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and the next wave would be worse. In twenty fifteen,
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new court filings in the United States again referenced Andrew's name.
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The same photograph reappeared, reprinted endlessly. Commentators debated what it meant,
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what could be proven, what was speculation. Each repetition deepened
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the damage. In twenty nineteen, Jeffrey Epstein was arrested again,
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this time on federal charges of sex trafficking miners. He
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was found dead in his jail cell weeks later, in
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what authorities ruled a suicide. That same year, renewed focus
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turned to Ghislaine Maxwell, who would later be convicted in
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the United States of conspiring to recruit and groom victims
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for Epstein's abuse. She is serving a lengthy sentence. Today.
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Andrew was not charged with any crime, but he was
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again in every headline. Each new revelation in the United
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States reignited questions. In Britain, charities began to distance themselves.
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Military units quietly sought reassignment of their royal patronages. Public
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support evaporated. In early twenty twenty two, Virginia Juffrey filed
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a civil lawsuit against Andrew in New York. The case
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was settled that February. The settlement included no admission of wrongdoing,
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but the damage was complete. After that, the process of
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separation between the Duke and the institution accelerated. Honorary military
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roles were removed, public appearances were curtailed, invitations dried up.
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The Palace phrased its statements in language that balanced compassion
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with finality. Throughout Andrew maintained his innocence. He continued to
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deny all allegations, insisting that the truth would vindicate him,
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but in the court of public opinion, verdicts rarely wait
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for evidence. Within the family, the response was quiet but decisive.
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The Queen, ever loyal to her children, reportedly continued to
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offer private support. Charles, who would soon become king, believed
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that the monarchy could not afford sentiment. William, now watching
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the machinery of consequence up close, understood that the survival
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of the institution would always outweigh personal ties. Three images
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remained at the center of it all. The London flat,
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the New York Park, the Manhattan doorway. They were not
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proof of guilt, but they were evidence of judgment, or
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the lack of it. For the monarchy, the lesson was
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sharp and enduring. Reputation is inheritance. Once lost, it cannot
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be reclaimed. The Queen lived her entire reign by the
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idea that the crown must be seen to endure. In
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the end, it did. The cost was a sun next time,
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a single interview meant to clear the air, instead destroys
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what little remained. While no one truly knows what happens
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behind closed palace doors.
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This entertainment series uses news sources, on the record, quotes,
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and some artistic license. Some moments have been dramatized for
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storytelling effect. To keep up with the modern day Royal family,
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follow our sister podcast, Palace Intrigue, a seven day a week,
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ten minute update on the Royals, Crown and Controversy, is
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a production of Caloroga Shark Meets Executive producers Mark Francis
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and John McDermott
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00:07:17.000 --> 00:07:20.920
93
00:07:21.959 --> 00:07:25.079
94
00:07:25.079 --> 00:07:31.000
95
00:07:31.040 --> 00:07:35.319
96
00:07:35.360 --> 00:07:41.680
97
00:07:42.079 --> 00:07:46.319
98
00:07:46.639 --> 00:07:50.199
99
00:07:50.240 --> 00:07:54.079
100
00:07:54.240 --> 00:07:59.519
101
00:07:59.519 --> 00:08:04.680
102
00:08:04.720 --> 00:08:08.920
103
00:08:08.959 --> 00:08:12.600
104
00:08:12.600 --> 00:08:17.560
105
00:08:17.680 --> 00:08:20.360
106
00:08:21.360 --> 00:08:25.279
107
00:08:25.519 --> 00:08:28.680
108
00:08:28.800 --> 00:08:34.120
109
00:08:34.720 --> 00:08:38.200
110
00:08:38.240 --> 00:08:43.279
111
00:08:44.679 --> 00:08:49.480
112
00:08:49.519 --> 00:08:53.440
113
00:08:53.480 --> 00:08:57.200
114
00:08:57.960 --> 00:09:02.080
115
00:09:02.120 --> 00:09:06.600
116
00:09:06.679 --> 00:09:11.720
117
00:09:11.799 --> 00:09:17.360
118
00:09:17.360 --> 00:09:21.080
119
00:09:21.120 --> 00:09:25.279
120
00:09:26.360 --> 00:09:29.759
121
00:09:29.799 --> 00:09:34.039
122
00:09:35.360 --> 00:09:40.799
123
00:09:40.799 --> 00:09:44.399
124
00:09:45.399 --> 00:09:47.840
125
00:09:47.879 --> 00:09:51.840
126
00:09:51.919 --> 00:09:55.840
127
00:09:56.320 --> 00:10:00.960
128
00:10:01.240 --> 00:10:15.279
129
00:10:15.840 --> 00:10:19.360
130
00:10:19.879 --> 00:10:25.720
131
00:10:26.039 --> 00:10:30.240
132
00:10:30.279 --> 00:10:35.120
133
00:10:35.759 --> 00:10:40.240
134
00:10:40.320 --> 00:10:43.759
135
00:10:43.799 --> 00:10:48.440
136
00:10:48.440 --> 00:10:51.600
137
00:10:51.639 --> 00:10:55.559
138
00:10:55.840 --> 00:10:59.720
139
00:11:00.399 --> 00:11:03.440
140
00:11:03.480 --> 00:11:08.440
141
00:11:08.440 --> 00:11:14.279
142
00:11:14.600 --> 00:11:19.799
143
00:11:19.799 --> 00:11:25.120
144
00:11:25.159 --> 00:11:28.519
145
00:11:28.600 --> 00:11:33.039
146
00:11:33.399 --> 00:11:37.320
147
00:11:37.360 --> 00:11:42.000
148
00:11:42.080 --> 00:11:47.240
149
00:11:47.919 --> 00:11:51.600
150
00:11:51.679 --> 00:11:57.159
151
00:11:57.200 --> 00:12:02.080
152
00:12:02.279 --> 00:12:05.519
153
00:12:05.600 --> 00:12:09.960
154
00:12:10.879 --> 00:12:15.120
155
00:12:15.159 --> 00:12:20.000
156
00:12:20.000 --> 00:12:24.080
157
00:12:24.159 --> 00:12:28.000
158
00:12:28.000 --> 00:12:33.279
159
00:12:33.399 --> 00:12:36.879
160
00:12:37.519 --> 00:12:41.240
161
00:12:41.399 --> 00:12:45.320
162
00:12:45.399 --> 00:12:48.639
163
00:12:48.679 --> 00:12:54.960
164
00:12:54.960 --> 00:12:59.679
165
00:12:59.720 --> 00:13:03.360
166
00:13:03.399 --> 00:13:10.279
167
00:13:10.679 --> 00:13:14.639
168
00:13:14.879 --> 00:13:30.200
169
00:13:30.240 --> 00:13:31.720
170
00:13:32.240 --> 00:13:36.279
171
00:13:36.720 --> 00:13:41.600
172
00:13:41.679 --> 00:13:47.240
173
00:13:47.919 --> 00:13:52.799
174
00:13:53.399 --> 00:13:57.840
175
00:13:57.879 --> 00:14:04.120
176
00:14:04.200 --> 00:14:05.440
