He Who Dies with the Most Laugh Wrinkles Wins isn’t just a punchline. It’s the actual motto behind this episode.
Chill-Rob McD grew up on Staten Island. Officer training, he jokes, was spent “validating the left side of the bell curve.” Now he joins the show to talk C-141s, close calls, and the book he wrote about surviving both.
Chill-Rob almost washed out of OTS at Lackland. Marching did him in — no rhythm, he says, a “public safety issue.” Still, he squeaked through and graduated in December 1988.
From there it was straight into jets — T-37s, then T-38s, at Columbus Air Force Base in Mississippi. He became a T-38 instructor pilot.
Then came the jump every new pilot dreads. A 12,000-pound trainer gave way to a 325,000-pound C-141 Starlifter. There was no transition training in between.
The Starlifter treated him well. Actually, he calls it “an honest plane” — reliable engines, forgiving controls, a familiar big-wing feel. It also handed him some of the wildest nights of his career.
He Who Dies with the Most Laugh Wrinkles Wins: The Devil Flight
The story he calls “flying with the devil again” starts with a rough takeoff out of Willow Grove. It gets worse from there. Somewhere over the Atlantic, at 35,000 feet, the plane slid into a Dutch roll.
A bad yaw damper turned out to be the culprit. Killing it snapped the nose hard right. Several wild rolls followed before the crew wrestled the jet level again.
Maintenance couldn’t duplicate the fault. So the crew launched for Kuwait the next night anyway.
Circuit breakers popped on taxi. The tower radioed that they were “shooting sparks” on rotation. Consequently, the crew declared an emergency and circled back.
Ground crews found the brakes glowing red hot. All four right-side tires blew on landing. A ruptured line trailed a wall of flame fifty feet down the runway.
Three days later, Chill-Rob deadheaded home with the cockpit voice recorder wedged between his legs. The safety investigator sat right across from him. “Not a lot of people have two mishaps in 48 hours,” the investigator said.
There’s more where that came from. A gunman demanded a landing fee off the coast of Africa. A loadmaster once yanked a snagged cable near the elevator controls, mid-flight.
Furthermore, Chill-Rob’s book, Flight Path: An Irreverent Aviation Tale, covers the whole career in that same voice.
However you feel about swept-wing aerodynamics, this episode earns its title. He who dies with the most laugh wrinkles really does win.








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