True Crime Obsessed – Episode 466: "Trainwreck: Mayor of Mayhem" (Netflix)

Date: November 4, 2025
Hosts: Jillian, Patrick Hines, Katie
Episode Theme:
A comedic, deeply engaging, and cutting recap of Netflix's “Trainwreck: Mayor of Mayhem”—the wild, scandal-rich political rise-and-fall of Toronto’s infamous Rob Ford. The hosts dissect Ford's underdog beginnings, viral controversies, chaotic leadership style, personal demons, and the cultural context that enabled his improbable ascent to power—with signature TCO humor, sass, and heart.

Episode Overview

This episode recaps the documentary chronicling Rob Ford, Toronto’s notorious mayor. With sharp wit and disbelief, the hosts explore how Ford went from being a political joke to the chief of Canada’s largest city, only for his administration to implode amid substance abuse, corruption, and bizarre press moments—while drawing sometimes-unavoidable parallels to American political figures.

1. Setting the Scene: Toronto in Turmoil (00:41–05:15)

• 2009 garbage strike: Toronto is buried in trash, leading to civic chaos and political opportunity.
  • “Let me tell you, the raccoons have never been happier.” – Patrick [03:54]
  • “Pay them whatever the hell they want.” – Jillian on sanitation workers [05:11]
• Mayor David Miller is “politically wounded” and steps down, leaving a leadership void.

Memorable Banter

• Ongoing jokes about raccoons thriving in garbage (possible podcast running bit).
  • “The raccoons are like stacking pizzas for the humans.” – Jillian [06:10]

2. The Ford Family Legacy & Daddy Issues (05:26–13:13)

• Rob Ford’s rise is painted as a desperate attempt to please his overbearing, political father.
  • “All of these men in the world trying to work out their daddy issues through politics is so exhausting.” – Jillian [12:54]
• His brother Doug's big influence—doubling down on “blowhard clown” vibes.

Host Commentary

• Hosts openly mock the Ford family's loud, confrontational style, and connect father-son politics to dysfunctional leadership.
  • “Taking it out on all of us.” – Patrick on politicians’ personal baggage [13:00]

3. A Political Joke Turns Serious (13:41–17:20)

• Rob Ford launches his mayoral campaign with clever publicity stunts, relying on “everyman” branding.
  • “He was the yelly blowhard, but all of a sudden...the journalists start to take him seriously.” – Jillian [17:34]
• Ford has a reputation for personal outreach—giving his business card (with cell number!) to anyone, and physically solving constituents’ problems.
  • “Here's my card. You need something, you call me.” – Jillian [16:36]
• Hosts compare Ford’s rise to Donald Trump, noting the populist appeal and media-savvy chaos.

4. Rob Ford’s Record: Scandal & Populism (17:47–23:43)

• Ford’s background: DUI, marijuana possession, drunken outbursts (e.g., hockey-game incident)—yet his popularity grows.
  • “That apology...we will hear no less than 10,000 times.” – Patrick on Ford’s “I’m only human” excuse [18:52]
• His controversial statements and political incorrectness resonate with underrepresented voters.
  • “If you're not doing needles and you're not gay, you won't get AIDS. Probably.” – Rob Ford, quoted by Patrick [11:24]
• Discussion of supporters loving his “anti-elite” attitude, even when it means embracing bigotry or dysfunction.
  • “Because it allows them to say things...they thought they had to hide.” – Patrick [19:25]

5. From City Hall to Circus: Ford’s Mayoral Reign (22:59–29:47)

• Ford’s first year is “productive but brutal”—undoing taxes, making transit workers essential (they can’t strike).
• Host insight on Ford’s politics: “very right wing populist positions, anti-immigrant, pro-nationalism.” – Katie via Patrick [23:14]
• Mounting concerns: coaching high school football on city time, fundraising scandals, clear conflicts of interest.
  • “Running from cameras and reporters to avoid questions—running.” – Patrick [24:29]

Key Quote

• “If you agree with me, I’ll work with you. If you don’t, I will destroy you.” – Mark quoting Rob Ford’s early philosophy [22:31]

6. Demonizing the Media & The Crack Tape Scandal (29:47–41:02)

• Ford and his allies wage war on the media, echoing familiar modern American tactics.
  • “Rob Ford demonized the media years before Donald Trump did the same thing.” – Jillian [29:00]
• Investigative reporter Robin Doolittle’s experience of being harassed for reporting Ford's misdeeds; media mistrust explodes.
  • “I just didn’t understand how much people distrusted the media and how successful the Fords had been at framing the media as a political opponent.” – Robin [40:20]
• The infamous crack video emerges: Robin is shown the footage in a clandestine parking lot deal on April Fool’s Day.
  • “Leave your bag, leave your phone, get in this car, go to the second location.” – Jillian [36:35]
• The media can't buy the video, but Gawker runs a story, giving the Toronto Star the opening to confirm.

Quotes

• “Yes, I have smoked crack cocaine. But no, am I an addict? No.” – Rob Ford, press conference [53:37]
• “My response would be: ‘Don’t worry, girl, there's no video. Wink, wink.’” – Patrick on denials [39:30]

7. Collapse at City Hall: Denial & Downfall (41:19–65:48)

Chief of Staff Mark: The (Only) Adult in the Room

• Mark tries to get Ford into rehab; instead, Ford fires him publicly.
  • “Mark was the North Star. Now Mark is gone and made an example of.” – Patrick [42:32]
• With Mark out, chaos worsens: Ford is caught on more videos, loses control at city council meetings, and his brother Doug Ford takes center stage.

Unbelievable Soundbites & Outrageous Behavior

• Legendary press conference: Ford denies sexually harassing a staffer, then adds:
  • “I've got more than enough to eat at home, thank you very much.” – Rob Ford [59:33]
• Hosts and reporters are openly flabbergasted by his crudeness and lack of shame.
  • “The reaction from the media is unbelievable.” – Jillian [59:54]
• Ford caught on video ranting in a Jamaican accent at a fast food place—yet his inner circle continues to make excuses.

City Council Tries to Stop the Mayhem (64:01)

• Council removes Ford’s mayoral powers in what devolves into a chaotic melee.
  • “Rob Ford...knocks into this council member Pam McConnell, knocks her over...” – Jillian [64:39]
  • “There’s a fucking melee on the floor.” – Patrick [64:24]

8. The Aftermath: More Videos, No Shame, and the Tragic End (65:58–70:02)

Refusal to Quit

• Despite scandals, Ford runs for re-election; comes close but ultimately loses the mayoral seat.
• His brother Doug runs and loses, but Rob wins a city council seat with 58% of the vote.

Final Act

• While on a “redemption” press tour (including wrestling and media spectacles), Ford is hospitalized with aggressive cancer. He dies in March 2016.
  • “It’s just like, this is the kind of ego we're dealing with here.” – Patrick [69:55]

Legacy & Reflection

• Supporters and close staffers vie to remember Ford’s “good side”—but the hosts point out the toxic mix of dysfunction, populism, and enablers.
  • “He could have started out in a good place... His demons got the better of him, and everybody around him let it happen.” – Jillian [71:29]
• Debate on political accountability and surrounding oneself with “good people” vs. cultivating power at all costs.

Notable Quotes & Moments

• On the Trump Parallels:
  “The pre-Trump parallels cannot be ignored.” – Jillian [15:06]
• On Handling Scandal:
  “You can’t have a mayor who is chronically smoking crack. You can’t have that.” – Jillian [67:35]
• On Demagoguery:
  “This is how it starts, because...it makes people think, ‘Oh, I can do that.’” – Patrick [19:38]
• On Ford’s Lasting Influence:
  “Two things can be true. He could have started out in a good place...but his demons got the better of him, and everybody around him let it happen.” – Jillian [71:29]

Episode Structure/Timestamps for Key Segments

• Intro & Raccoon Garbage Strike: 00:41–05:15
• Ford Family & Campaign Start: 05:26–13:13
• Campaign Parallels, Populism: 13:41–17:20
• Rob Ford Scandals Unfold: 17:47–23:43
• Mayoral Mayhem & Manipulating Media: 22:59–29:47
• Crack Video & Media Fallout: 29:47–41:02
• City Hall Chaos & Firing Mark: 41:19–42:32
• Downfall and Relentless Denial: 42:49–65:48
• Final Days, Death & Legacy: 65:58–71:29

Conclusion

In this wickedly funny and exasperated episode, True Crime Obsessed’s hosts trace the arc of Rob Ford: from populist upstart to international punchline, from “man of the people” to symbol of political dysfunction. The team deftly unleashes their signature blend of humor and righteous outrage upon Ford’s antics—while teasing out the darker themes of enablers, the erosion of media trust, and the global rise of shameless populists.

“Mayhem is such a good word.” – Jillian, closing out the episode [73:07]

Listeners walk away entertained, incredulous, and with new appreciation for Canadian raccoons—and maybe wary empathy for anyone with Jerry or Tom as their right-hand man.

Next Episode Preview:
The Perfect Neighbor (Netflix) – listener advisory for graphic bodycam content!

For full comedic effect and impassioned commentary, listen to TCO Episode 466 wherever you get your podcasts.