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Edward VIII caused a constitutional crisis with his abdication, dismay with his wartime associations and an ongoing headache to the royal family.
Today, Prince Andrew and Prince Harry’s very different exits from their roles as working royals provide their own ongoing challenges.
Pod Save the King host Ann Gripper is joined by historian and author Alexander Larman to reflect on the echoes between then and now - including a powerful video message and royal memoirs that made uncomfortable reading.
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Writing The Windsors
Queen's message of hope on coronavirus
Harry and Meghan's new life begins
When royals visit Ireland
Prince Charles gets coronavirus
Royals respond to coronavirus crisis
Meghan and Harry's royal reunion at Commonwealth service
When the royals come to town - the reporters' view
Sussex statement ruffles feathers
Harry and Meghan's new Big Day - 100 episodes later
Meghan and Harry's exciting future and how to get there too
Queen back to work - and completes 68th year on throne
Royals remember the Holocaust and address the future
The Palace and The Press - Part 2 - Media law lecturer
The Palace and The Press - Part 1 - IPSO, the press regulator
Harry and Meghan deal done - and dissected
Prince Harry and the Cambridges back to business
Queen's Sandringham summit statement sets the tone of Sussexit
Harry and Meghan quit The Firm - now what?
Royal review of the year
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