53: In the Bag pt.2: How to Hide a Painting

Grant Thomas
May 15, 2024
3 min read

Updated: May 1

Jump back into one of the greatest unsolved heists in history? In Part 2 of our deep dive into the Isabella Stewart Gardner Museum theft, Grant and Maia pick up the story 48 hours after 13 masterpieces vanished—and the chaos really kicks in. From a scrapped smoke-bomb plan in the ’80s to Myles Connor’s audacious Rembrandt heists, they trace a tangled web of mobsters, shady art dealers, and maybe a few guards who weren’t as innocent as they seemed. Follow the trail through Boston’s underworld, meet a cast of characters straight out of a crime novel (looking at you, Billy Youngworth and Bobby Donati), and find out how a dark warehouse, a reporter with a flashlight, and a handful of suspicious paint chips almost cracked the case—almost. With living suspects, mob wars, FBI blunders, and jaw-dropping theories about where the art could be today, this episode delivers the twists, the drama, and a few moments that'll have you shouting, "Wait, WHAT?!" right along with us. Hear the perspective of Boston Herald journalist Tom Mashberg. We chase leads and go down rabbit holes and yet are still left wondering - how to hide a painting.

Chapters/Key takeaways to listen for

[00:00:00] Catch Up
[00:18:45] How to Hide a Painting
[00:33:15] Smoke-Bomb Shenanigans: How Louis Royce’s 1982 garage pyrotechnics almost walked away with that lone masterpiece
[00:40:20] Blue-Room Blind Spot: The one painting that never tripped the alarms
[00:58:30] Warehouse Whistle-Blow: Tom Mashberg’s 1997 Boston Herald sting uncovered
[01:29:00] The Last Insider: Keys to where those masterpieces might be hiding
[01:45:00] Vault Hunters: The ground-penetrating radar sweep of Gentile’s CT lair
[01:48:30] Deathbed Confession: Hand over the art tonight, and you die a free man
[01:52:00] Case Still Open: Why this half-billion-dollar heist remains unsolved
[01:55:10] Keep Your Eyes Peeled: How rumor-hunters are scouring estate sales, private collections, and whispered mob legends for a breakthrough
[01:58:00] Sign-Off Shenanigans: A trademark banter, mac-and-cheese confessions, and how to stay in touch after the credits roll

Photos Referenced:

Quotes:

“A single paint chip can swing the tides in a half-billion-dollar crime.” - Grant Thomas
“Donati’s killing or disappearance always signals a shift in power, and the trail goes cold.” - Grant Thomas
“A simple mix-up erased the strongest physical proof.” - Maia Warner
“He showed the underworld what you can do when law enforcement negotiates.” - Maia Warner

Connect with Us

Love a good laugh? Stay in the loop with the Well, I Laughed Podcast! Hit up wellilaughed.com for all the fun, throw some love our way on Patreon at https://patreon.com/WellILaughedPodcast, and send us your wildest listener stories at wellilaughedpod@gmail.com—because let’s be real, we know you’ve got some!