In this Canadian history / true crime-adjacent episode, we explore the real story of Gary Hoy, a corporate and securities lawyer at Holden Day Wilson in Toronto, Ontario, whose bizarre accidental death in 1993 became an internet meme, urban legend, and staple of “dumb ways to die” lists:

Toronto in the 1980s–1990s

The rise of glass-and-steel skyscrapers in downtown Toronto
The design and reputation of the Toronto-Dominion Centre (TD Centre) as a modern corporate landmark
Who was Gary Hoy?

A well-regarded Bay Street lawyer known for confidence, precision, and intense risk assessment skills
His work in corporate law and securities law and his reputation as a charismatic showman with law students and visitors
The famous window demonstration

Hoy’s repeated stunt: running into the shatterproof glass windows to show off the building’s engineering
How he trusted the safety glass and misunderstood the structural frame and system design
July 9, 1993 – the fatal incident

A tour for articling students / law graduates at the TD Centre in downtown Toronto
Hoy sprints at the 24th-floor window; the glass does not break, but the entire pane detaches from the frame
Hoy falls into the building’s atrium, is killed on impact, and the story hits Canadian news, radio, and eventually the internet
Engineering, safety, and design lessons

Why the shatterproof glass technically “worked” but the overall system failed
How Hoy’s death appears (often unnamed) in engineering textbooks, safety case studies, and discussions about system resilience, design strength, and misuse vs. intended use
From tragedy to meme and dark comedy

How media and the public framed him as an arrogant lawyer who underestimated risk
Why his death became a darkly comic legend, shared on Reddit, YouTube, and true weird history forums
The uncomfortable line between real tragedy, gallows humour, and viral internet stories
Small Talk Dimension (banter & personal stories)

Rhys and Jesse talk Montreal winters, Canadian weather, and the brutal cost of travel and flights
Jesse’s cheap vacation to Cuba during shortages, all-inclusive resorts, ethics, and adventure
A story about Rhys’ car (Mustang) and winter driving mishap
Running jokes about risk, bad decisions, and the recurring bit: “What’s irritating your tits?”
If you like darkly funny Canadian stories, weird deaths, and strange but true history from Canada, hit follow and support the show on Patreon at patreon.com/canadaisboring for bonus episodes, extra small talk dimension segments, and more bizarre Canadian stories.

00:00 – Intro: Canada Is Boring & Today’s Topic
00:24 – Teasing the Story of Gary Hoy
02:02 – Welcome to Canada Is Boring (Show Open)
02:26 – Toronto in the 1980s: Glass Towers & TD Centre
02:56 – Who Was Gary Hoy? Bay Street Lawyer Background
03:54 – Law Nerd, Risk Assessment & Stress-Testing Systems
05:32 – Showman Lawyer: Office Tours & Glass Demonstration
06:38 – Running at the Shatterproof Glass
07:56 – “Please Tell Me This Is How He Died”
07:56 – July 9, 1993: The Fatal Demonstration
08:41 – The Window Pane Detaches: 24-Story Fall
09:36 – Aftermath, Media Reaction & Meme-ification
11:01 – Engineering Lessons: System vs. Component Failure
12:10 – Wrapping the Gary Hoy Story

12:57 – Entering the Small Talk Dimension
13:22 – “What’s Irritating Your Tits?” Segment
13:48 – Montreal Winters & Planning a Working Vacation
14:25 – Flight Costs, Last-Minute Travel & Life Chaos
15:18 – Choosing Cuba During Shortages (Ethics & Adventure)
16:38 – Talking Cuba: Socialism, First Class, and Tipping
18:19 – Rhys’ Winter Driving Mishap & The Car in a Ditch
20:03 – Street Fucker vs. Snowstorm
20:21 – 4 a.m. Airport Run & Travel Sleep Strategy
21:01 – Maybe Recording from Cuba & Tech Limitations
21:31 – Outro: Patreon Plug, YouTube, and Rich F*ck Stories
22:10 – Closing Music / End