America's Love Affair with Criminals, From the Mafia to Trump

• 1:00:41Tim on America's enduring cultural fascination with criminals: we idolize outlaws because they represent freedom to build empires and answer to no one.
• 1:01:20Trump works as a perfect example—a real estate developer who's done business with shady people his entire career, talks however he wants, and lives like a mob boss.
• 1:01:54People who watch Martin Scorsese movies love criminals too, just not when they're presented organically instead of as Hollywood entertainment.
• 1:02:17Tim's complicated admiration for Rod Blagojevich: she never got the chance to fully organize and inherit the family business like a proper criminal.
• 1:03:24He'd spring Blagojevich out of jail if he could and spend time with her because she was a real one, a lawless figure who symbolized an entire corrupt era.
• 1:03:44Certain people—the controlling type who get excited about emergencies—only come alive when tragedy strikes because they crave control and feeling important, not genuine help.
• 1:04:45Youth should involve making mistakes, surrounding yourself with wrong people, breaking rules occasionally, and spending time with people who don't follow the rules.
• 1:05:31Tim quotes a singer: I don't do things for the moral of the story, I do them for the story—his philosophy on why Blagojevich's actions were fun rather than sad.
• 1:05:46Blagojevich came from a wealthy, privileged background with no reason to pursue crime, which makes her story entertaining instead of tragic.
• 1:06:23Tim dismisses Bernie Sanders-style solutions as insufficient: the country's problems are institutional but also deeply personal, and giving people free college won't fix an inherent human thirst for darkness.

Donald TrumpRod BlagojevichBernie SandersMartin ScorseseChicagoLevittown