rant · moment 10 of 15
Road Trip to Chicago and Meeting Blagojevich's Wild Mother
from #186 - Blagojevich | The Tim Dillon Show · #186
7 min
Tim recounts driving to Chicago with the dogs, meeting Blagojevich's tough trucking mother, and reflects on how the relationship eventually ended with his friend moving on to another woman and further heroin addiction and prison time.
- Tim's friend came from money in Chicago suburbs, but had just enough to want more and was drawn to scams and cons.
- They drove to Rod Blagojevich's house to drop off dogs after Tim and his friend had been squatting in another guy's apartment in New York.
- Blagojevich's mother was 300 pounds, chain-smoked Marlboro menthols, drank Grande frappuccinos, drove a big truck and screamed on the phone—a tough, no-nonsense businesswoman.
- They celebrated St. Patrick's Day together in Chicago, got drunk, and watched the river get dyed green.
- The friend later started dating another woman from Long Island, they both got into heroin, and she's now serving almost a decade in prison.
- Tim reflects that truly fun people are grifters, con artists, and criminals—not boring people like substitute teachers talking about grading papers.
- If someone is a con artist, cheater, grifter, or derelict but fun at dinner, it's worth knowing them because you're only on the planet once.
- The friend would call Tim with updates about Blagojevich being in trouble legally, then making bail and getting out so they could all go to dinner together.
BlagojevichApplebee'sLong IslandChicago