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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

19. Josephus Was One of the Jewish Revolt’s Most Brilliant Commanders

Turncoat - Ambush and destruction of a Roman column near Bethlehem early in the Great Jewish Revolt — Ambush and destruction of a Roman column near Bethlehem early in the Great Jewish Revolt. Pinterest

Josephus, a 29-year-old priest, was chosen to lead the rebel forces in Galilee. He used a combination of guile and force to bring the region under his control. In one ruse, he bluffed the town of Tiberias to surrender with an overwhelming display of force from a navy of 230 boats. Unbeknownst to the Tiberans, the boats carried no more than five men each. After early setbacks, however, the Empire struck back, and the Roman general Vespasian was sent to crush the revolt. Vespasian, with his son Titus, marched his legions from Syria into Judea, with Galilee as his first stop. Josephus gathered an army, but its undisciplined ranks broke and ran at the first sight of the Roman legions, and fled to the hilltop town of Jotapata.

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.