John Graham, Canada’s Quiet Spy in Castro’s Cuba.

The story of John Graham, a Canadian diplomat in 1960s Cuba who became an unlikely spy during the aftermath of the Cuban Missile Crisis. Because the United States had no embassy or formal presence in Cuba after the revolution, President John F. Kennedy quietly asked Canadian Prime Minister Lester B. Pearson for help. Pearson turned to Graham, a reserved career diplomat rather than a James Bond‑style operative, and tasked him with confirming whether the Soviets were actually removing their nuclear weapons from the island.

Graham declined CIA spy gadgets, including a covert camera, because being caught with obvious espionage equipment would have been too dangerous. Instead, he relied entirely on his remarkable memory, driving around Cuba in check shirts and khakis, observing troop movements, equipment, missile silhouettes, and radar installations from the outside, then returning to the Canadian embassy each day to reconstruct everything from memory, down to distances, serial numbers, and layouts.

His detailed reports, cross‑checked with imperfect high‑altitude spy photography, helped reassure Washington that the Soviets were indeed complying, contributing quietly but significantly to the de‑escalation of the crisis. For this work, Graham received no parade or public recognition, simply continuing his career as a successful Canadian diplomat.

0:00 – Cuba vs Canada: Setting the Scene
Jesse records from a Cuban resort, Reese in snowy Canada; resort life, Wi‑Fi and VPN woes.

2:05 – Intro: Canada Is Boring (Podcast Cold Open)
Show intro montage about Canada’s “boring” reputation and episode setup.

2:26 – Episode Start & Terrible Wi‑Fi
Hosts properly introduce the episode, joke about audio quality and Cuban “Crisis Wi‑Fi.”

2:53 – Cuban Missile Crisis 101
Reese explains the Cuban Missile Crisis, nukes in Cuba vs Turkey, and Cold War brinkmanship.

6:45 – Why Is Cuba Still Treated This Way?
Discussion about ongoing US–Cuba tensions, ideology, exiled Cubans, Obama/Trump policy swings, and the dollar vs Canadian dollar.

9:58 – Canada’s Role in Cuba
Canada’s embassy in Havana, trade ties, and why Canadians move easily through Cuba.

10:45 – JFK’s Secret Request to Canada
JFK asks PM Lester B. Pearson for help; introduction of Canadian diplomat John Graham, “Canada’s quiet spy.”

13:10 – A Very Un‑Bond‑Like Spy
John Graham’s background, attitude toward CIA/KGB, and becoming a reluctant Cold War spy.

18:04 – The Spy Who Remembered Everything
Graham refuses a spy camera and relies on his memory: troop movements, distances, missile silhouettes, guard routines.

19:36 – How He Gathered Intel on the Ground
Driving around Cuba, timing convoys, watching radar dishes, then reconstructing everything at the Canadian embassy.

21:15 – Verifying the Blobs from the Sky
How Graham’s reports complemented low‑res spy plane photos and helped confirm missile removal.

22:21 – Life After the Mission & His Book
Graham’s quiet diplomatic career and his book Whose Man in Havana: Adventures from the Far Side of Diplomacy.

27:24 – Sun‑Roasted Meatballs & Bad Champagne
Hilarious anecdote from the Dominican Republic reception: “carbonated moose piss,” food poisoning, and knocking out half the cabinet.

29:19 – Entering the Small Talk Dimension
The “STD zone” stinger and a shift into looser small talk and gross jokes.

31:10 – Modern Cuba Crisis: Fuel & Tourism (2025–2026)
Hurricane Melissa, US raid on Maduro, oil cutoff, Mexico halting shipments, and airlines repatriating tourists; Jesse’s on‑the‑ground impressions.

33:24 – Cash Problems & Two‑Tier Pricing
No cash, no cards, e‑transfers via Canadians, and learning about tourist vs local pricing in Cuba.

36:27 – Resort Culture & 24/7 Drinking
Observations about “resort people,” cheap watered‑down booze, smoking, and why people pay to drink abroad.

38:36 – Reviewing the Canadian Embassy in Havana
Reading out hilarious 1‑star Google reviews of the Canadian embassy and what people expect from an embassy.

42:29 – Fax Me Later & Sign‑Off
Running jokes about fax machines, refilling the diarrhea spy car, and episode wrap‑up with the outro song.