412: The Killing of William Woodward w/ Jerry Aylward

Most Notorious! A True Crime History Podcast

Erik Rivenes

True Crime, History, Education

4.7 • 2.8K Ratings

🗓️ 5 November 2025

⏱️ 65 minutes

🔗️ Recording | iTunes | RSS

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Summary

In the early hours on a rainy autumn night in 1955, on a lavish country estate in Oyster Bay Cove, esteemed New York socialite Ann Woodward fired both barrels of her custom-made shotgun into the head of her husband, multimillionaire William J. “Billy” Woodward Jr., killing him. She mistook him for a notorious prowler who preyed on the privileged class. At least that was what the official reports stated. The police focused on catching the prowler, as they cast an impenetrable dragnet around the “Playhouse” for the elusive intruder. However, as with many other aspects of Billy and Ann’s social circle, things were not always as they appeared. Retired detective Jerry Aylward, author of "Murder on the Gold Coast: The Killing of William Woodward", discusses with us the uncomfortable truths behind one of the Gold Coast’s most notorious murders. The author's website: https://www.jerryaylward.com/ The author's Amazon page: https://www.amazon.com/stores/Jerry-Aylward/author/B0841NGVSZ Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Hello, this is Matt and McKinley from History Dispatches.
0:07.6	We are the father-son duo bringing you the weird, the wild, the wacky, and the craziest tales from across time.
0:13.2	From the Ice Bowl to the Great Heathen Army.
0:15.8	And the head of Oliver Cromwell.
0:17.6	The same head they kept on a pike for three years?
0:20.1	Yep, all here on History Dispatches.
0:22.7	New episodes every weekday. Find out more at History Dispatches.com or wherever you get your podcast app.
0:30.2	Hi, everyone. A quick note before we start, this episode includes a homophobic slur.
0:38.1	It appears in the historical context of a true crime case
0:41.1	and is part of the true account our guest is discussing.
0:45.0	It's included to reflect the story accurately,
0:48.4	not to hurt or insult anyone.
0:51.8	Listener discretion is advised.
0:53.6	Music assault anyone. Listener discretion is advised. Welcome, my friends to another episode of the Most Notorious podcast. I'm Eric Rivenis.
1:25.0	Let's get this show on the road. It is so great to have retired detective
1:29.7	and criminal investigator, Jerry Aylward, back on the podcast. We first talked, and last talked,
1:38.7	in 2020 about Francis Tugan Crowley. That was episode number 181.
1:46.8	He has returned with another book.
1:48.9	This one is called
1:50.2	Murder on the Gold Coast,
1:52.5	The Killing of William Woodward.
1:55.3	And it is really great
	...

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