Windsors & Losers

Latest Episodes:

Kate and William, The Royal "Good Double Act" Oct 06, 2026

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Can't you just picture it: Prince William and Princess Kate side-by-side, ignoring their dishwasher in favor of hand cleaning the plates and utensils from dinner? That's the happy domestic picture Kate painted on a recent engagement, while elsewhere in England, Princess Anne took a principled stand against... running. And finally, we recap a heck of a night in New York City that saw Charles Spencer and his wife, Former Nordic Person of the Year Dr. Cat Jarmon, venture out for a conversation with Tina Brown.

Book Club 2: Charles Spencer's Version Sep 29, 2026

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Princess Diana's little brother, Charles Spencer, has set the royal-watching world alight with his new memoir, Swan Song. In this Winsors & Losers Book Club, episode two, Eva and Allie assess Charles's version of his and Diana's childhoods and how their lives changed when she married the other Charles, the then Prince of Wales. Is Charles Spencer giving us revisionist history, or merely logging what he knows for the good of history? Is he actually continuing a feud with Diana's former butler Paul Burrell, or really just telling the world he dated South Africa's first supermodel, "Josie"? We recount all of this — and, of course — rank a Windsor and a Loser, in this week's episode.

Picking Sides in King Charles Vs. Charles Spencer Sep 22, 2026

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Earlier this year we bemoaned a lack of plot for the British royal family, and boy — have we gotten more than we wished for. On this publication day of Charles Spencer's book about his late sister, Princess Diana, we share our theories and appreciations about the revelations told so far and the damage it's all doing to the monarchy. Elsewhere, Harriet and Peter Phillips are still married and a unique rumor about William and Kate make the rounds.

Harry and Meghan's Elusive English Endgame Sep 15, 2026

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Prince Harry and Meghan Markle are settling into life in England, announcing upcoming engagements, posting lovely countryside Instagram Reels with the kids, and ruffling the feathers of their royal relatives. Business as usual, right? We muse on their English end game, and touch on two very royal scandals affecting King Charles.

Harry, Meghan, and the Hamptons of England Sep 01, 2026

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It's been a week since the news of the millennia dropped that Prince Harry and Meghan Markle were moving back to England. Well, they're there — and now, the world's press react. Eva and Allie share their four cents on the couple's quite lovely new neighborhood, while also tackling weighty issues such as a royal renaming controversy and Fergie's own return to Britain.

12 Semi-Educated Theories on Harry and Meghan's Return Aug 25, 2026

Show notes

August is usually a dull month for royal-watchers, but thanks to Harry and Meghan, the last four weeks have been a whirl of wind! Unless one resides under a sizable boulder, one would know that Harry and Meghan Sussex have decided to pick up sticks and trade Montecito, California for TBD, England. Today, hosts Eva and Allie share twelve theories about why, exactly, this move may be happening and why it matters. And, in other news, they discuss a bombshell from Princess Diana's brother and King Charles's wildly excessive gift to an artisanal craftsperson.

Book Club 1: The Serve-and-Tell Memoir That Changed Everything Aug 04, 2026

Show notes

Welcome to the inaugural edition of the Windsors & Losers Book Club. In lieu of a traditional weekly episode, Eva and Allie are launching a periodic mini-series about — in their humble opinions — the best royal biographies and autobiographies of all time.

The first episode goes back to the book that started a cottage industry of "serve-and-tell" memoirs, in which former royal employees lift the lid on what life is really like with the Windsor family. The Little Princesses, by Elizabeth and Margaret's one-time governess Marion Crawford, is a saccharine look inside the girls' wartime childhoods. But what happened next is the real story; Marion turned into something of a cautionary tale.

Have you read this book? Let us know what you think!

The Symbolism and Semiotics of Harry and Meghan's Holiday Snaps Jul 28, 2026

Show notes

It's holiday season, and that means vacation musings from Harry and Meghan — and us, as well. Hosts Allie and Eva reflect on their pilgrimages to various royal sites in England, and — more importantly — dissect what the Sussexes meant to convey with their carefully edited images from Portugal and England. In other news, James Middleton branches out in business and a storied royal home hits the market.

The Indomitable Harriet Sperling and Peter Phillips Jul 07, 2026

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The Indomitable Harriet Sperling and Peter Phillips

Radio Play: 50 Minutes at Clarence House Jun 30, 2026

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Come with us, won't you, as we imagine what exactly King Charles and Prince Harry discussed during their fateful fifty minute meeting at Clarence House last September. In Windsors & Losers's first (and possibly last) radio play, our intrepid (and unencumbered by a potential absence of acting talent) hosts take on the roles of father and son to imagine what happened on September 10, 2025. It's a timely reflection, we hope, being that Harry plans to visit London again this week with the intention of once again seeing his father after years of estrangement.

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