Dale Remling decided he’d had enough of life behind bars at Jackson Prison.
A small-time crook and big-time con man, Remling was a displaced cowboy from out west who came to Michigan and landed himself in Jackson by writing bad checks and stealing hogs. On June 6, 1975, he left the world’s largest walled prison via a helicopter flown into the prison yard.
The chopper whisked him away to the woods in nearby Leslie, where he eventually hitched a ride into town, enjoyed a good meal and then pretty much just waited for the cops to come arrest him. He was free for 30 hours total, and to hear him tell it, those were the 30 best hours of his life.
Remling’s daring escape landed him on the evening news and on the front page of every newspaper in America, and it got him his 15 minutes of fame. He deserved a lot more than 15 minutes. His story has largely been lost to history, which is too bad, because it has all the elements of a Hollywood blockbuster. Or a Netflix docuseries at the very least.
Michigan’s most famous prison break had it all: A wild plot involving a crazy gang on the outside making it all happen. A housewife with eight kids who was smitten with Remling and was the brains of the operation, hiring a bunch of 20-year-olds to pull it off. Prison guards who let a helicopter drop into the prison yard and carry an inmate away without even getting a shot off.
And most of all, this story has a charming villain the likes of which Michigan had never seen before. Dale Remling was a bad guy, sure, but a charmer just the same. He never killed or hurt anyone and even the people he swindled swore he was a great guy. He had a huge grin and looked like a cross between Clint Eastwood and Evel Knievel.
So while we wait for Hollywood or Netflix to discover the story, here’s the tale of a true Michigan original—Dale Otto Remling, the rapscallion who flew the coop and never came to regret it.
Remling was born in 1928 in a farmhouse in the Oklahoma panhandle, the son of a cattle farmer. He was one of eight children and the family moved around a lot out west, living in Kansas, Nebraska, Texas and Wyoming at various times before settling in Bakersfield, California.
They had a celebrity in the family, as well. Remling’s niece Phyllis was married to Buck Owens, the famous country singer and star of “Hee Haw.” Dale knew him well.
Remling was a cowboy through and through. He did some boxing as a kid but spent most of his younger years on the rodeo circuit riding bulls. In the early 1950s, he got married to a Native American woman in Nevada, one of three marriages he had. She had a son named Jimmy who Remling basically adopted.
It was also about this time that Remling began his life of crime, primarily small-time larcenies. He eventually got caught on a forgery charge in 1954 and sent to Soledad Prison in California. Remling didn’t much care for prison life, so in 1955, he escaped by walking away from his job at the prison dairy. They caught him and sent him back to finish the rest of his sentence.
He got out in 1962 and went back to prison in 1964, convicted of writing bad checks and stealing an airplane. Remling got out in 1966 but went back to prison six months later for violating his parole. He made another prison break in 1971, walking away from the Sierra Conservation Camp medium-security prison.
Deciding it was probably best to leave California, Remling made his way to Michigan and landed in a small town in Montcalm County called Sidney, population 100. It’s about an hour northeast of Grand Rapids.
Back in 1951, Remling had stolen the wallet of a man named Jimmy Mangan and kept the identification papers inside it. When he got to Sidney 20 years later, he identified himself as Jimmy Mangan and said he was a rich rancher from Colorado.
Dale Remling, or Jimmy Mangan, quickly began to charm the pants off everyone in Sidney. They all loved the good-looking cowboy from Colorado, and he spent time riding horses and holding court at the local bar, telling grandiose tales of his life out west.
He also began to borrow money from the locals, telling them he’d pay it back when he went back to Colorado to sell some of his cattle. The folks in Sidney were happy to give him whatever he asked for. The small-time thief was now a big-time con man.
The prettiest girl in town fell in love with Mangan. Her name was Kay Petersen and she was a local schoolteacher and the daughter of the richest man in Sidney, Don Petersen, who owned all the businesses in town. Kay and Jimmy got married in January 1973.
That’s when his lies and cons began to catch up to him. Remling had written a lot of bad checks that were about to bounce and he needed a huge infusion of cash to cover everything. He hooked up with a guy from nearby Greenville named Dennis Gerbracht and he convinced Gerbracht to help him pull off a caper.
Remling knew of a family farm in Hooper, Nebraska, that had about 400 hogs. Remling’s plan was to drive to Hooper, take the family hostage, then steal all the hogs and drive them to Iowa and sell them. Dale and Dennis took off for Nebraska and stole the hogs. The plan fell apart at the state line when they were stopped by the cops and asked to produce vaccination records for the hogs. When they couldn’t, the police realized the hogs were stolen.
Remling somehow bolted before the cops figured it out, but Gerbracht got caught, convicted, and sent to prison.
When Remling made his way back to Sidney, everybody was on to him. All the checks had bounced, the police somehow figured out that Jimmy Mangan was actually a prison escapee from California named Dale Remling, and he was arrested, convicted and given a 6- to 10-year prison sentence and sent to Jackson.
The authorities in Nebraska gave him a seven-year sentence for stealing the hogs, as well, and told him it would be served concurrently in Michigan. His marriage to Kay was annulled.
Remling went to Jackson Prison on Aug. 29, 1973, and almost immediately started planning his escape. He knew very well the story of Joel David Kaplan, an American businessman who had been convicted of murder in Mexico in 1962.
In 1971, Kaplan escaped from his Mexican prison using a helicopter his sister had rented. Kaplan and his cellmate made it to freedom because the guards mistakenly thought the helicopter landing was an official visit. They made it all the way to California and when Mexico didn’t seek extradition, Kaplan remained a free man.
This was the basis of a 1975 Charles Bronson film called “Breakout,” which coincidentally came out just three weeks before Remling’s breakout. Everyone thought that Remling had gotten the idea from “Breakout,” but it was actually the true story that was his inspiration.
Remling loved the tale of how Kaplan escaped, so he wanted a helicopter to swoop into the Jackson Prison yard and carry him to freedom. He started hatching the plan just weeks after he got to Jackson.
He was 46 years old the day he escaped, and he later told reporters that he opted for the helicopter option because, “That was the easiest way. I didn’t have enough nerve to try the wall. I’m getting a little old for that.”
He knew he needed an accomplice on the outside to arrange for the helicopter and the getaway, and he found the perfect one in Gertrude Woodbury, a 43-year-old mother of eight who lived in Webberville.
One of Gertrude’s sons, Kenneth, was doing time in Jackson for breaking and entering. Gertrude visited Kenneth often, and it was in the prison visiting room that she met Dale Remling, the handsome cowboy with the huge smile.
She began to visit Dale as often as she visited her own son and it was during one of those conversations that Dale pitched the idea of her organizing his helicopter prison break. Dale lied and told her that he had $60,000 hidden on the outside that she could use to pay the gang she assembled.
Woodbury was totally smitten with Remling, so she agreed to handle all the details. She had spent some time working at a traveling carnival, so she started by reaching out to some of the young carnies she worked with.
She needed someone who would fly the helicopter, another person to drive the getaway car, and she needed a couple more people to drive decoy cars. That way, if the cops tracked the chopper to the drop site after the escape, they wouldn’t know which car to chase.
She found her pilot: Morris Colosky, a 20-year-old fellow Webberville resident who had worked at the carnival with her. She recruited three women to be the drivers: Susan Hill and JoAnn Van Patten, both of whom lived a little north of Howell and Jolyne Conn of Webberville. Gertrude also enlisted another one of her sons, 19-year-old Calvin, to help with some of the details.
The Remling Gang was in place.
The most important job belonged to Colosky, who had to learn how to fly a helicopter and then rent one on the day of the escape. He crashed a helicopter in Howell during his first training attempt, though, so he gave up that plan and decided he would hijack one instead. He’d pull a knife on the pilot and force him to fly to Jackson.
After months of planning, the escape was set for June 6, 1975. Remling had been meticulously studying the guards and their routines. He noticed that the lone guard watching the yard always took a bathroom break at the same time every morning.
“The guy in the tower that was closest was an old guy,” he told the Detroit Free Press in 1984. “I knew that every day between 11 a.m. and 11:05, he’d be in the toilet. Imagine him when he heard that chopper.”
Remling and Woodbury set the escape for exactly 11:05 a.m. on June 6. Remling would lay down a red bandana in the prison yard so Colosky would know exactly where to land the chopper.
At 10:15 a.m., Susan Hill drove Colosky to the Mettetal Airport in Plymouth, which had a charter helicopter business on site. Colosky was wearing a suit and tie and went inside and told the pilot, a 29-year-old Vietnam vet named Richard Jackson, that he needed a flight to Lansing immediately for an urgent business meeting. Jackson told him it would cost $170. Colosky paid him in cash. Away they went.
Just a couple minutes after they were airborne, Colosky pulled a knife, held it to Jackson’s throat, and told him they were going to the prison. And they needed to be there exactly at 11:05 a.m.
Remling was at his job in the prison stamping plant, and exactly at 11 a.m., he took a break and went out to the yard. He heard the chopper before he saw it and he knew the escape was on. Was he nervous?
“I think every cowboy will tell you the same things,” he told the Free Press in 1976. “Before they get on a bull or climb down that chute, they’re afraid. You’re nervous and your hands are sweating. But when you sit down on that bull, you’re OK. When the gate opens, you’re just like we are now, sitting and talking.”
At exactly 11:05 a.m., the helicopter landed in the yard. The one guard who was supposed to be watching the yard was inside taking a dump. All the guards in the other towers looked in that direction and wondered what the hell was happening, but by the time they realized it was an escape, Remling had already climbed aboard and the chopper had taken off.
That was the first time that Dale Remling had ever met Morris Colosky, and he had no idea that Colosky had hijacked the helicopter. He thought the pilot was just another accomplice, so as soon as they took off, Remling slapped Richard Jackson on the back and said, “Great job, buddy!”
Colosky then handed Remling a knife of his own and told him it was actually a hijacking.
“After this, I think a minute,” Remling said in 1976. “What in the hell do I want with this knife? What am I going to do? Open the door and if the tower starts shooting, throw it at them?”
Gertrude Woodbury’s plan was for the helicopter to get to the ground as soon as possible to let Remling out. The longer it was in the air, the more time the cops would have to track it. So they arranged for a drop-off point near Leslie, about 11 miles north of the prison. There would be three cars waiting there—one to take Remling and the other two to drive away as decoys. Colosky would hop into one of the decoy cars.
That’s when the plan went to hell. When they landed, Colosky sprayed mace in Jackson’s eyes, but it only blinded him for a few seconds. He took off and hovered over the car that had Remling inside, ready to track it wherever it went. Remling realized what was happening, so he told the driver to beat it and he ran into the woods. He had $100 in his pocket that he’d taken from the pilot.
“All I wanted to do was get away from there,” he said. “I could just see about 15 police cars with red lights coming across the field.”
Remling spent the night of June 6 in the woods, getting scratched by bushes and eaten by mosquitoes. In the morning, he emerged from the woods and hitched a ride into Leslie with a passing motorist. He told the driver his car had broken down while on a fishing trip and gave him $10 for the ride. By now, his face was all over the news and every cop in the country was looking for him.
When he got to Leslie, he went to a restaurant, where he enjoyed a hamburger, a piece of pumpkin pie and some coffee. He said it was the best meal he’d had in years.
About 2:30 p.m., police got a tip that there was a “strange man walking around the streets.”
Several plainclothes troopers went to Leslie and spotted Remling coming out of a grocery store. They observed him as he walked into Huffie’s Bar. The cops walked in, pulled a gun and told him to raise his hands.
Dale offered no resistance. He just turned around and smiled at them. His freedom lasted all of 30 hours, and he loved every second of it.
On the way back to the state police post, Remling and the arresting officer, State Police Trooper Bill Flower, just talked about horses. After they booked him, the cops took Remling back outside and let him hold an informal press conference in front of all the reporters.
By this time, the women who had driven the cars and Calvin Woodbury had all been caught and arrested. Colosky and Gertrude, however, high-tailed it to Kansas and started working at a carnival there. They spent 18 days on the lam before they were finally caught and returned to Michigan.
When they were all sentenced later that year, the judge came down hard on Morris Colosky and Gertrude Woodbury, giving them each 20 years in federal prison for air piracy and other charges. Colosky ended up serving six years, earning parole in 1981 and keeping his nose clean since then.
Colosky is still around and living in mid-Michigan. Michigan Enjoyer contacted him for this story and asked if he’d be willing to do an interview and he politely declined. “You would probably get better information just filing a FOIA request with the federal court for my statements there,” he said.
Calvin Woodbury, Susan Hill, Jolyne Conn, and JoAnn Van Patten all pleaded guilty and only received probation.
Gertrude Woodbury served a few years in federal prison and resumed her life as a housewife and mom in the Lansing area. She passed away in 2022 at age 90, and her obituary made no mention of this adventure.
As for Dale Remling, he only served eight more years. He began the rest of his sentence in Jackson, but when the guards there started hassling him for making them look bad, he asked for and received a transfer to the federal prison in Marion, Ill.
He got out in 1983 and came back to Michigan, renting a farm in Mecosta County and generally staying out of trouble. He eventually moved back to California and passed away in 1999 at age 71. A lifelong smoker who loved his unfiltered Camels, he was in very poor health at the end.
The story doesn’t end there, though. When Remling died, his family didn’t have enough for a proper burial, so they just buried his ashes in a mobile-home park in California, underneath a rock that had his initials, DOE, on it.
In 2024, his stepson Jimmy Williams, the Native American boy he had adopted in the 1950s, decided to make it right. He dug up his stepfather’s ashes and took them to the Fish Lake Valley Cemetery, located in the middle of the desert in Dyer, Nevada, near where Remling lived when he was married to Jimmy’s mom.
Williams, who is a preacher now, dug a hole with an auger and buried Dale Remling’s ashes there. He recorded it and put the whole thing on YouTube. Then he went back to his church and delivered a eulogy.
“He may have been an outlaw part-time, but he was a great man in my life,” Williams said.
Rest in peace, Dale Remling. An outlaw, to be sure, but a Michigan original.
Buddy Moorehouse teaches documentary filmmaking at Hillsdale College.
