{"id":256010,"date":"2026-10-26T21:57:02","date_gmt":"2026-10-27T02:57:02","guid":{"rendered":"https:\/\/gunsamerica.com\/digest\/?p=256010"},"modified":"2026-10-26T21:57:08","modified_gmt":"2026-10-27T02:57:08","slug":"garrett-trapnell-hijacking-story","status":"publish","type":"post","link":"https:\/\/gunsamerica.com\/digest\/garrett-trapnell-hijacking-story\/","title":{"rendered":"Garrett Trapnell: The Con Man Who Sparked 3 Hijackings"},"content":{"rendered":"\n

<\/path><\/svg><\/span><\/span>Estimated reading time: <\/span>11<\/span> minutes<\/span><\/p>\n\n\n\n

Garrett Trapnell was a career criminal, master manipulator, and convicted airplane hijacker whose influence inspired two women to attempt extraordinary prison rescues. What followed involved a .45-caliber pistol, a hijacked helicopter, another commandeered airliner, and one of the strangest crime stories of the 1970s.<\/p>\n\n\n\n

Garrett Trapnell: The Charming Con Man With a Criminal Mind<\/h2>\n\n\n\n
\"College
My dad was an all-American football player in college. Sadly, those genes seemed to have skipped me.<\/figcaption><\/figure>\n\n\n\n

My mom was a beauty queen, and my dad was a football star. Tragically, I didn\u2019t seem to inherit any of that. Don\u2019t feel sorry for me. I still ended up with plenty of other cool stuff. My parents are both freaking awesome. Much to most of what I am today I owe to their genetic influence, longsuffering tutelage, and superlative examples. However, that nature versus nurture thing runs in the other direction as well.<\/p>\n\n\n\n

\"Photograph
This is the face that captivated at least eight different women. I honestly just don’t get it. Social media photo.<\/figcaption><\/figure>\n\n\n\n

Garrett Brock Trapnell was born in 1938 in Brockton, Massachusetts. As near as I could tell, this guy just came from the factory broken. He lied about stuff when telling the truth would have been easier. His classic old-school crime spree spanned two decades.<\/p>\n\n\n\n

Trapnell often passed himself off as a CIA agent as part of his cons. He robbed any number of banks across Canada before cleaning out a jewelry store in Freeport, Bahamas, of $100,000 worth of gems and sundry baubles. Along the way, he married at least six different women that we know of. Garrett Trapnell was a card-carrying full-time professional sociopath.<\/p>\n\n\n\n

Here\u2019s what is so weird. Despite being a pathological liar and an unrepentant polygamist, the women who hooked their wagons to Trapnell’s horse really did seem to fall for him. One in particular demonstrated her love for the man in a truly compelling fashion.<\/p>\n\n\n\n

How Garrett Trapnell Used the Insanity Defense to Escape Prison<\/h2>\n\n\n\n
\"Historical
By acting like an unhinged crazy person, Garrett Trapnell frequently kept himself out of prison. Public domain.<\/figcaption><\/figure>\n\n\n\n

Trapnell was an unrepentant criminal, but he was also exceptionally smart. This is a rare and dangerous combination. When he was inevitably apprehended, he would often act utterly deranged and have his lawyers put forth an insanity defense. This technique got him committed to mental institutions rather than prison. It was easier to break out of insane asylums or change his behavior and be declared \u201ccured\u201d so that he could once again breathe free air.<\/p>\n\n\n\n

This approach toward the criminal justice system was actually quite effective right up until 1972 when Garrett Trapnell stepped over an invisible line. That was when he hijacked TWA Flight #2 from LA to New York. Hijacking was much more common back then than it is now. Garrett Trapnell raised it to an art form.<\/p>\n\n\n\n

TWA Flight 2: A .45-Caliber Pistol and a $306,800 Demand<\/h2>\n\n\n\n
\"Historical
Garrett Trapnell put his arm in a fake cast so he could smuggle a handgun onboard a commercial airliner. That ultimately ended poorly for him. Social media photo.<\/figcaption><\/figure>\n\n\n\n

On 28 January 1972, Trapnell boarded this cross-country passenger flight with a fake cast on his arm. Concealed within the cast was a .45-caliber automatic pistol. Once airborne in the vicinity of Chicago, Trapnell broke out his hogleg and laid out his demands.<\/p>\n\n\n\n

Trapnell had lost a recent court case and owed his attorneys a great deal of money. As a result, he demanded $306,800 in cash for starters (about $2.5 million today). In addition, he mandated the safe release of Angela Davis. Davis was a philosophy professor at UCLA and an avowed communist. She purchased firearms for a small group of African-American terrorists who used the guns to kill a judge and several hostages during a failed escape attempt from a California courtroom. Acquitted of these charges later, Davis’ legal travails had become a cause celebre for the radical Left. Just to make sure there would be a happy ending to this sordid tale, Trapnell also made the safe release of the hostages contingent upon an unconditional pardon from President Richard Nixon.<\/p>\n\n\n\n

Any idiot could have told him that this ridiculous plan was destined for failure. A disguised FBI agent shot and wounded Trapnell once they landed at Kennedy Airport. No one else was hurt. Trapnell recovered in short order, but that wild adventure landed him in federal prison.<\/p>\n\n\n\n

\"Historical
This is Angela Davis, the radical terrorist UCLA college professor who was likely indirectly responsible for killing a sitting judge. Social media photo.<\/figcaption><\/figure>\n\n\n\n

Garrett Trapnell’s Insanity Defense Meets a Federal Jury<\/h2>\n\n\n\n

At his trial, Trapnell once again played the crazy card. He claimed to suffer from both schizophrenia and multiple personality disorder while vehemently asserting his innocence throughout. He explained that the guy who committed the hijacking was actually some dude named Greg Ross. The rub was that Ross seemed to have been physically occupying Trapnell\u2019s body at the time of the crime.<\/p>\n\n\n\n

The prosecution had done their homework this time. The government produced a recording made several months prior to the hijacking wherein Trapnell boasted to a journalist concerning how convincing he could be when pretending to be stark raving mad. Despite such compelling evidence, this trial still ended in a hung jury when one juror, a social worker by profession, failed to convict. This just goes to show that people are idiots.<\/p>\n\n\n\n

Four months later, Trapnell was finally convicted of hijacking during his retrial. He was sentenced to life in prison and locked up at USP Marion in Williamson County, Illinois. Marion was the country\u2019s first designated supermax prison. Now, hold that thought\u2026<\/p>\n\n\n\n

Barbara Oswald: The Woman Who Hijacked a Helicopter for Trapnell<\/h2>\n\n\n\n
\"Photograph
Barbara Oswald corresponded heavily with Garrett Trapnell in prison and eventually died trying to break him out. Social media photo.<\/figcaption><\/figure>\n\n\n\n

Once on the Inside, Garrett Trapnell kept himself busy trying mightily to get out. He had an undeniably charismatic personality in the same vein as that of Charles Manson. Manipulating people was kind of his superpower. His target du jour was a female friend named Barbara Ann Oswald. Oswald was actually a Staff Sergeant on active duty in the Army.<\/p>\n\n\n\n

On 24 May 1978, SSG Oswald took leave and hijacked a civilian charter helicopter based in St. Louis and piloted by a Vietnam veteran named Allen Barklage. Oswald forced Barklage at gunpoint to fly to Marion with the intention of liberating both Trapnell and one of his scumbag friends, Martin McNally. McNally was quite the character in his own right.<\/p>\n\n\n\n

McNally was incarcerated for having hijacked an American Airlines Boeing 727 in June of 1972. He demanded $502,500 (where do they get these specific sums?) and then leapt out of the plane with a parachute over Peru, Indiana. Unlike DB Cooper, the cops scooped him up in short order.<\/p>\n\n\n\n

Anyway, Barklage flew Oswald to the prison as directed. Just before touchdown, he grabbed the woman\u2019s gun and a struggle ensued. Here\u2019s where things got interesting.<\/p>\n\n\n\n

The Bell 206 Helicopter Hijacking That Ended in Gunfire<\/h2>\n\n\n\n
\"Bell
This is a Bell 206 not fundamentally unlike the machine commandeered by Barbara Oswald in her failed attempt to free Garrett Trapnell from prison. Wikipedia photo by MarekW.<\/figcaption><\/figure>\n\n\n\n

Google claims the aircraft was a Bell 206 JetRanger II. This is the civilian version of the militarized OH58. I flew OH58 Aeroscouts operationally for Uncle Sam myself back in the day. Fighting somebody while simultaneously flying a JetRanger isn\u2019t much like the movies.<\/p>\n\n\n\n

If you let go of the controls of an OH-58 in flight, the aircraft will gradually roll upside down and kill you. I honestly cannot imagine trying to go mano-a-mano, even with a small woman, while trying to keep the greasy side down. Tom Cruise and James Bond can do that, but I sure couldn\u2019t. Apparently, however, Allen Barklage had more in common with those awesome action movie guys than he did with me. He wrestled the gun away from Oswald and shot her dead while also successfully landing the helicopter. That’s a horrible story, but, wow, what a stud.<\/p>\n\n\n\n

Robyn Oswald Hijacks TWA Flight 541: The Nightmare Continues<\/h2>\n\n\n\n
\"Trans
This is a DC9 of the sort that Robyn Oswald hijacked in an effort to get Garrett Trapnell freed from prison. Wikipedia photo by Jetpix.<\/figcaption><\/figure>\n\n\n\n

Seven months later in December of 1978, Barbara Oswald\u2019s 17-year-old daughter Robyn boarded TWA Flight 541 in Louisville, Kentucky. Flight 541 was a McDonnell Douglas DC9 destined for Kansas City International. There were 87 souls on board.<\/p>\n\n\n\n

Once the plane reached cruising altitude, Robyn stood up and calmly announced that she was wearing a bomb and that she now had control of the airplane. Witnesses later described her as gorgeous and completely at ease throughout. News releases afterward characterized her as a \u201ccalm, cool, and collected doll.\u201d I’m not sure how that description would go over in the mainstream media today. Robyn demanded that Trapnell be freed or she would blow up the plane.<\/p>\n\n\n\n

The pilots diverted to Williamson County Regional where the FBI got involved. After a tense nine hours on the ground, FBI hostage negotiators eventually orchestrated a peaceful resolution to the crisis wherein no one was harmed. The bomb was found to have been a handful of railroad flares wired to a doorbell. As she was a juvenile at the time, the details of her charges were never made public.<\/p>\n\n\n\n

Three Hijackings, Two Women, and Garrett Trapnell’s Deadly Influence<\/h2>\n\n\n\n

If I\u2019m counting correctly, that\u2019s at least four different aerial hijackings at play in this sordid tale. Barbara Oswald considered herself Trapnell\u2019s girlfriend at the time. Right, wrong, or otherwise, Robyn either believed Trapnell to be her actual father or at least viewed him as a father figure in her life.<\/p>\n\n\n\n

Tragically, Allen Barklage perished due to injuries incurred in a helicopter crash twenty years later in 1998. McNally, the parachuting hijacker, was paroled in 2010. Despite a fair amount of effort, I couldn\u2019t figure out what became of Robyn beyond that her time in prison had been brief.<\/p>\n\n\n\n

Garrett Trapnell’s Final Years: Solitary Confinement and a Grim Ending<\/h2>\n\n\n\n
\"Historical
Garrett Trapnell’s sundry psychopathologies finally caught up with him. He spent the last portion of his life sitting alone in a tiny jail cell. Social media photo.<\/figcaption><\/figure>\n\n\n\n

By now the good folks who ran the supermax prison at Marion had lost their patience with Garrett Trapnell. He was placed under a \u201cNo Human Contact\u201d order and remanded to solitary confinement for the rest of his days. Journalist Eliot Asinof published a book about Trapnell\u2019s life titled The Fox is Crazy, Too. In it, he describes Trapnell as an inveterate career criminal with a genius-level IQ but no functional conscience.<\/p>\n\n\n\n

A decent psychiatrist could have had a field day with Garrett Trapnell. I would start with antisocial personality disorder and work out from there. However, such organically defective people seldom make wise life choices. Trapnell, for his part, was a voracious consumer of cigarettes.<\/p>\n\n\n\n

\"Garrett
Garrett Trapnell was a genuine piece of work. He spread chaos everywhere he went. Find-a-Grave photo.<\/figcaption><\/figure>\n\n\n\n

In 1993, a dying Garrett Trapnell was transferred to the United States Medical Center for Federal prisoners in Springfield, Missouri. Emphysema was predictably killing him. On 7 September of that year, the master con man who so deftly manipulated women while claiming to be a CIA agent got to meet Jesus face-to-face. He was 55 years old. I obviously wasn\u2019t there, but I suspect he had some pretty serious explaining to do.<\/p>\n\n\n\n