The Dollop #724: Garrett Trapnell - Part Two (March 10, 2026) Hosted by Dave Anthony & Gareth Reynolds

Episode Overview

In this episode, comedians Dave Anthony and Gareth Reynolds continue their exploration of the wild true-life tale of Garrett Trapnell—a compulsive conman, bank robber, skyjacker, charming manipulator, and folk legend with a flair for the dramatic and a knack for escape. Picking up after Part One, the hosts delve into Garrett's escalating crimes, his hunger for adrenaline, bizarre alter egos, manipulative legal defenses, and the utterly chaotic trail of destruction, broken hearts, and hijackings he left behind.

Key Discussion Points & Insights

Garrett’s New Life and Cycles of Crime

• Reinvention in LA: After another escape from a mental institution in 1969, Trapnell creates the new persona "James W. Stewart", brokering a fake military background and landing a job selling cleaning chemicals to the army base. He marries Susan, confessing his criminal past—she stays loyal regardless.
  • “She’s too in love with him to care.” – Dave [05:53]
• But…The Cycle Continues: Garrett can’t escape his compulsions. He begins conning grocery stores with bad checks, netting $600,000 (in today’s money).
  • “Most people would be like, $50, and you’d scam or whatever...he made over 600 grand doing this.” – Dave & Gareth [07:52, 07:54]
• Springing an Accomplice: Garrett engineers a daring escape for his friend George Padilla from a mental institution—George simply bulldozes through during a shift change. [09:00]

Bank Robberies and International Flight

• Escalation: Not content with cons, Garrett teams up with George and robs a bank in Montreal, returning to the US successfully.
• Narrow Escapes: The duo evade law enforcement through near-comedic strokes of luck—fog at JFK allows Garrett to slip away to St. Louis unnoticed with the FBI waiting at the wrong gate. [13:10]
  • “He just jumps onto the first flight out of JFK before they could nab him.” – Dave [13:09]

Personal Chaos and Failed Attempts at Going Straight

• Attempt at Legitimacy: Inspired by guilt, Garrett tries (and spectacularly fails) to run a dog-breeding farm for security firms in Baltimore, resulting in hilarious hypothetical business pitches involving monkeys, children’s brains, and sharks.
  • “The future is monkeys with guns on the back of German shepherds that we grow in Baltimore farmland.” – Gareth [18:08]
• Backlash and Violence: His attempts at social justice, like hosting Black children on the farm (“Guilty Pastures”), provoke his racist wealthy neighbors, culminating in four dogs killed by a sniper. [22:16]

The Criminal Spiral

• Back to Crime: Fleeing Baltimore, the couple try to settle in SF, but paranoia sends Garrett on the run again. When Susan gives birth, the FBI is waiting at the hospital; Garrett flees, gets busted en route to Mexico, and faces dozens of charges. [24:10]
• The Legal Ploy—Greg Ross: Playing psychologists, Garrett claims he's sometimes overtaken by a sinister alter ego named “Greg Ross”, a Dr. Jekyll/Mr. Hyde defense that works repeatedly.
  • “He made his shrink believe that the entire crime binge had been a burst of schizophrenic mental illness and that he was now totally okay.” – Dave [26:15]

The Hustle Escalates: Showgirls, Yachts & International Crime

• Garrett charms, cons, and leaves a trail of scammed showgirls, stolen credit cards, dodged ex-wives, and elaborate thefts (robbery at a Bahamian jewelry store, then a daring plane escape). [37:05–41:36]
• Collaborates with another conman, Roger Peterson, and even attempts to blend into southern aristocracy by marrying a debutante and robbing Canadian banks monthly ("Butch Cassidy and the Sundance Kid”). [46:46–48:09]

Descent into Destruction: Skyjacking and Psychological Warfare

• Adrenaline Junkie: Increasingly reckless, Garrett’s fixation on spectacle and near-suicidal risk climaxes with a skyjacking—a fake cast hides his gun as he takes over a TWA flight, demands ransom, and requests political prisoners’ freedom.
  • “You are being hijacked. Act naturally and lead the way to the cabin...I have a pistol and there is a bomb in the aircraft.” – Garrett's note [63:01–63:42]
• Confronting the System: On the phone with a psychologist, Garrett offers a damning critique of the prison/mental health system:
  • “You rob a man of five years of his life, and he comes back in a society without having left anything for himself...these correctional institutions...they don’t build anything.” – Garrett (quoted by Dave) [69:24–69:53]
• Betrayed and Set-Up: While negotiating at JFK, Garrett surrenders leverage by freeing the hostages, is shot while being tricked by FBI agents in disguise, and tried again—still falling back on the Greg Ross defense, manipulating jurors and earning a mistrial. [71:37–73:12]

The Final Years & His Unbelievable Legacy

• Nixon’s Law & Order: The government hammers for a conviction. Garrett is finally sentenced to life in prison. [74:03]
• The Cult of Trapnell—Mother-Daughter Hijackers: While in prison, his story inspires Barbara Oswald (who dies attempting a helicopter prison break for him) and later her daughter Robin, who attempts to hijack a plane at 17 to demand his release, using road flares as a fake bomb. [77:06]
• Prison Years: Garrett becomes an infamous prison celebrity, paints, studies languages, never betrays accomplices, and dies in 1993 of emphysema. [77:30]

Notable Quotes & Memorable Moments

• “This guy’s life is insane.” – Dave [47:10]
• “He can’t be stopped...He’s like Neo.” – Gareth [56:53]
• “He finally felt free...Free of lies and deceit. Free of the world that he built around himself.” – Dave [51:02–52:00]
• “You rob a man of five years of his life...these correctional institutions...they don’t build anything.” – Garrett (via Dave) [69:24–69:53]
• “Can you imagine getting a mother-daughter hijack combo...that is nuts.” – Gareth [77:30]

Important Segment Timestamps

• Garrett assumes 'James Stewart' identity and confesses to Susan [03:35–05:53]
• Bad checks scam nets $600k [06:27–07:54]
• Breakout of George Padilla [09:00–09:42]
• Narrow escape from FBI due to fog at JFK [13:09–13:26]
• Dog-breeding farm fiasco & Baltimore chaos [16:10–20:08]
• Dog-sniper incident, return to California [22:16–22:28]
• Greg Ross defense first deployed [24:47–26:41]
• Bahamian jewelry store heist & Miami plane escape [37:05–41:36]
• Monthly Canadian bank robberies as Butch Cassidy & Sundance Kid [46:46–48:09]
• First skyjacking & manifesto on the system [62:47–69:53]
• Mother-daughter hijackings inspired by Trapnell [75:50–77:30]

Tone & Style

• The episode is filled with Gareth’s improvisational bits, inventive character voices, and surreal hypothetical business pitches (dog-growing, monkeys with guns), keeping a light, absurdist, and sarcastic tone even while discussing dark subject matter.
• Dave acts as the semi-straight man, providing historical facts and summarizing events, while Gareth reacts with incredulity, dark humor, and frequent asides.
• The episode shows a blend of true crime, dark comedy, and cultural commentary, characteristic of The Dollop.

Summary/Takeaways

This episode chronicles a true American antihero—Garrett Trapnell—whose relentless need for excitement, manipulation, and challenge led to decades of crime, social engineering, and an improbable cult following, culminating in copycat skyjackings and a lasting folk legend. The story is a wild romp through the crime-laden 1970s, skirting the absurdity of mental health defenses, the shortcomings of law enforcement, and the allure of chaos. By the end, Dave and Gareth leave listeners debating whether a life of wild, reckless adventure—even at the expense of others—is preferable to one of dull convention.

Final Question (79:07):

“Would you rather live a brief life of just total chaotic fun or a long life of boring?" – Dave

Gareth: “Let’s go.” [79:25]

Source Material Mentioned

• “The Fox is Crazy Too: The True Story of Garrett Trapnell, Adventurer, Skyjacker, Bank Robber, Con Man and Lover” by Eliot Asinoff

(Advertisements, intros, and outros omitted. All timestamps in MM:SS format.)