Places/place

Cuba

2017-09-03, 2 mentions 2017-09-10, 1 mention 2017-11-20, 1 mention 2018-05-09, 1 mention 2021-04-11, 1 mention 2026-03-07, 1 mention

Every mention, in time. Each mark is a day — taller means more that day — and links to the moment.

Tim’s take

Most mentions are just trip-planning banter about a cruise stop, with jokes about ending up in a Cuban prison or playing dominoes there rather than any real position 46:19 1:00:30 34:19 50:06. When the subject turns political he's inconsistent: he concedes to his step-grandfather that the embargo pushed Castro toward the Soviets 33:50, while elsewhere he cites Cubans and Venezuelans fleeing to America on rafts as proof of what people escape when things work 24:46. Cuba itself also shows up once as a punchline in a Trump-invasion joke 5:27.”}

References: 7
Span: Sep 3, 2017 — Mar 7, 2026

Every Reference (7)

48:29Sep 3, 2017neutral#
"said no tourism. Did we talk about something show them going to Cuba? Not yet. I'm going to Cuba in October first time on a flight First"
Trump as a Rejected Organ Transplant and Corbyn's Anti-Imperialism — Joel Osteen's Ark+130s into the segment
52:41Sep 3, 2017joking#
"ISIS many times. It would be great if, I wonder if we have fans at Cuba. What an interesting question. Probably not. Can they get podcasts"
Ray's Sketchy Trip to Cuba as a Fake Missionary — Joel Osteen's Ark+156s into the segment
1:00:42Sep 10, 2017neutral#
"is Columbus Day but I'm coming back I think on Columbus Day from Cuba right so we need to get in before Halloween because there's a Veterans"
Planning the Halloween Episode: Johnny Gosch Road Trip Logistics — A Country of Laws+12s into the segment
42:44Nov 20, 2017neutral#
"gonna be you're gonna be climbing the walls. Yeah, we'll be in Cuba for a couple days Yeah, it'll be fun. Yeah And I guess we're going"
Trying to Reach Jack From Bullion Shark — Always Be Capturing+506s into the segment
33:57May 9, 2018neutral#
"back to pick it up and he was like, he just started in on me about Cuba and I'm like she knows I'm like he's like you're more conservative"
Arguing About Castro With His Step-Grandfather — The Montauk Project+7s into the segment
Apr 11, 2021neutral#
"you know like venezuelans cubans when they escaped uh you know they escaped to america they swam here on rafts or on their tt's back or whatever"
Reasonable People Fleeing to Austin as Cities Die — #247 - Scream At The Sky (ft. Yannis Pappas) | The Tim Dillon Show+13s into the segment
Mar 7, 2026joking#
"said he has said like I'm on a roll. Like let's go let's let's hit Cuba. Like I'm feeling good. Like he's he's It's 3:00 a.m. in Vegas"
Grim: Trump's Venezuela High and 'I'm on a Roll' Mentality — Emergency Podcast: Iran, Israel, & Imminent Destruction | The Tim Dillon Show #486+40s into the segment