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During the Herodian Period 37 BCE to 4 BCE, Herod was well aware of the strategic advantages of Masada.  He chose this site as his winter palace.  During Herod’s
reign, luxurious places were built in addition to well-stocked storerooms,
and cisterns.  After Herod died in 4BCE, the annexation of Judea to Roman
Empire in 6 CE, the Romans stationed a garrison at Masada.
Josephus relates one of the first events of the Great Revolt of the Jews
against the Romans,  in 66 CE was the conquest of Masada by the Sicarii
group.  The Sicarii got their names from the curved daggers they used.  They
were headed by Menahem, son of Judah the Galilean. He was murdered in
Jerusalem in 66 CE  Then Eleazar Ben Yair fled from Jerusalem to Masada and
became commander of the rebel community on the mountain.
According to Josephus, Masada was the last rebel stronghold in Judea.  In 73
CE the Roman Tenth Legion Fretensis, led by Flavius Silva, laid siege to the
mountain with 8000 troops, you can see remnants of their eight camps around
the base, a siege wall, and a ramp made of earth and wooden supports on a
natural slope to the west.  Captive Jews brought water to the troops,
probably from Ein Gedi.  The siege lasted a few months and the Romans
brought a tower with a battering ram up the ramp.  The rebels constructed an
inner support wall out of wood and earth, which the Romans then set ablaze.
Josephus describes when the hope of the rebels dwindled, Eleazar gave two
speeches where he convinced the elders of the 960 members of the community
that it would be better to take their own lives and the lives of their
families than to live in shame and humiliation as Roman slaves.  Two woman
did not follow Eleazar’s wisdom and hid with five children in a cistern when
the rest of the community were killed.  They told the Romans what had
happened that night on 15th of Nissan, the first day of Unleavened Bread.

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