[tomatocracy]

Yes, quite remarkable. Ross Perot was described as having organised "the largest jailbreak in history" for this (though I can't find the reference now), as several thousand prisoners escaped in the ensuing chaos.

[adamw2k]

Slightly different kind of jailbreak, but quite a bit larger than this one over the course of 28 years: https://en.wikipedia.org/wiki/Judy_Feld_Carr