I’ve been playing Borderlands: the Handsome Collection lately, and Handsome Jack is definitely one of my favorite gaming villains along with Kefka Palazzo from Final Fantasy VI and Revolver Ocelot in Metal Gear Solid and Metal Gear Solid IV: Grumpy Old Soldiers. Jack’s also my favorite sort of villain, an idealist who uses questionable methods because the end justifies the means.
Game Theory tackles Jack in this video, which is actually halfway decent.
Handsome Jack’s ultimate mistake, besides yielding to his paranoia and just casually murdering anybody who might be in a position to betray him (like the scientists who helped him liberate Helios Station), is a classic: he’s trying to impose order on Pandora and its people from above in the most literal sense possible given that he oversees events on both Pandora and its moon Elpis from a Hyperion (which means “watcher from above”) space station.
When you impose order from on high, you only escalate chaos. Order must arise out of chaos if its to have any hope of enduring.
One could even argue that Handsome Jack is the embodiment of the Law of Eristic Escalation, a fundamental Discordian concept.