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Turncoat Generals – Commanders From History Who Switched Sides

Khalid Elhassan April 3, 2025 17 min

Turncoat - Benedict Arnold — Benedict Arnold. Smithsonian Magazine

18. Cheating Death With a Rigged Lottery

The future Emperor Titus fights his way through Jewish rebels during the Siege of Jotapata. Imgur

Vespasian surrounded Josephus and his men at Jotapata, and after a siege that lasted 47 days, successfully stormed the town. Josephus and other rebel leaders fled to a secret hiding place down a well, but a prisoner told the Romans. The victors shouted an offer down the well for Josephus to surrender, as Vespasian wanted him alive. He wanted to surrender, but the other leaders insisted that they all commit suicide instead. So Josephus suggested they do so in an orderly fashion, by drawing lots, with the loser of each round getting killed by the others. He rigged the lots, and one by one the other leaders were killed, until Josephus was one of only two men left alive. At that point, he convinced the other survivor that they should surrender. They did, and while the other man was summarily executed, Josephus was taken in shackles to Vespasian.

Written by

Khalid Elhassan

A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.