Dale Otto Remling, a charismatic criminal, had spent two years constructing his scheme for a third escape from prison. This elaborate plan involved a helicopter and three “get-a-way / decoy” cars. Join Chuck and I as we investigate Michigan’s malicious marauder and head to Jackson State Prison for this curious caper.

The Helicopter Escape

At 10:15 am on June 6, 1975 a white helicopter soared over the walls of Jackson Prison. It landed near the stamping plant. A red bandana left on the ground had designated the landing spot. Stunned guards simply watched as a single prisoner ran to the chopper, climbed inside and flew into the air heading northwest.

Morris Colosky, a friend of Remling’s, had hired Richard Jackson, a helicopter pilot, to charter a flight from Plymouth to Lansing. After climbing into the air, Morris pulled out a knife and instructed Richard to fly to the Jackson Prison yard and land where the bright red bandana laid on the ground.

Within moments of touching down, inmate Dale Remling had darted out from between two buildings, where he’d been waiting. The trio rose over the largest walled prison in the world with 52 acres encapsulated by brick boarders and barbed wire.

Ken Wyatt, from a local newspaper, recounted the escape. “At the Citizen Patriot, something about a helicopter landing in the prison yard crackled over the police radio. From then on it was a three-way race between the escapers, police authorities and reporters.”

The Landing Site

A little red school house at M 106 and Meridian Road, six miles northwest, marked the rendezvous site where three cars were supposed to be waiting. Two would act as decoys while Dale’s girlfriend would drive the convict away.

Remling had sprayed the helicopter pilot, Richard Jackson, with mace to prevent being followed. The escapee and his accomplice hijacker, Morris Colosy, scrambled to the awaiting vehicles. The two decoy cars sped away leaving Dale apparently waiting for his partner.

The helicopter pilot had somehow managed to pursue one of the vehicles and notified the police. Those accomplices had been quickly apprehended. The authorities suspected that Remling became nervous and had decided to go on-foot, rather than by car.

A Night Alone

Dale took cover in the swampy woods and swatted mosquitos all night. He managed to get cleaned up and dressed in civilian clothes the following day. Dale Remling made his way north to the town of Leslie.

Dale Remling’s Biography Of Deception

Who was Dale Remling? Dale Otto Remling had ironically been born on Independence Day in 1928 in Hooker, Oklahoma. As the youngest of seven children, he dazzled his family and friends with charisma and confidence. He was athletic and musically talented. Dale had a lot of friends and could influence people with his natural leadership skills.

What brings a person to a life of deception and crime? From the outside it’s difficult to understand a person’s motivation and thought processes.

In the mid 1950’s Dale had stolen the identity of a U.S. Forest Service land appraiser, James J. “Jimmy” Mangan. Using this name, Dale would purchase merchandise with fraudulent checks, then sell the items for cash. Dale was arrested in 1955. He’d escaped from Soledad Prison south of San Francisco, California. Three days later, he was recaptured and served his newly extended, full sentence.

In the early 1970’s Dale had been convicted of stealing an airplane and sent back to Soledad Prison for his incarceration. Again, he escaped, but this time he relocated to the tiny village of Sidney in Montcalm County, Michigan.

In Michigan Dale Remling absorbed the identity of Jimmy Mangan. Dale played the role well as Jimmy was a well-liked, trusted citizen. Dale or “Jimmy” had even married the daughter of a wealthy gentleman who’d stated, “He was a very nice fellow, and everyone liked him; even the littlest child loved him.” Although “Jimmy” (Dale) had taken advantage of his own father-in-law.

With creditors constantly calling, Dale (Jimmy) had hatched a plan for quick cash with a friend from nearby Greenville. The pair traveled to Hooper, Nebraska and held up a hog farm at gunpoint. The duo drove off with nearly four hundred pigs, worth $70,000, and left eleven people locked in a truck. Dale had hoped to sell the herd in Iowa. However, without the proper paperwork, the pigs couldn’t be sold for what they were worth.

Back in Michigan, Remling, known as Jimmy Mangan, began buying merchandise with bad checks again, then selling the items for cash. He was arrested in Ionia county in 1973, where his true identity had been discovered. Dale Remling had been sentenced to seven years of hard labor in Jackson Prison for stealing the hogs along with additional time for the fraud charges. Thus began Dale’s planning for the helicopter escape.

Huffie’s Bar

Back to the breakout. Dale Otto Remling had just spent a long night in the mosquito infested woods. After shaving and dressing in new clothes, he made his way to Huffie’s Bar in Leslie, Michigan.

The quiet, polite and unassuming gentleman sat himself at the bar and ordered. Most customers never suspected that he’d been the escaped convict they’d heard about and were soon shocked by his capture.

Accounts vary as to who had notified the authorities, but when State Trooper William Flowers burst into the establishment, Dale Remling surrendered with a smile. As the two men waited outside for backup, Trooper Flowers and Dale Remling had chatted pleasantly about horses.

“Thirty hours and eight minutes later, his escape ended in a Leslie bar.” newspaper man, Ken Wyatt, shook his head. “Thirteen miles from his cell.”

“I think cages are for something other than people. You talk about problems with people, the prison system breeds it into you,” Remling had said following his arrest.  

New Sentence For Remling

Unfortunately for Remling, his thirty hours of freedom resulted in an extra ten years added to his 7-10 year sentence for writing fraudulent checks and stealing hogs. With the confirmed charge of ‘air piracy,’ Remling had earned another decade onto his incarceration.

Dale Remling’s charismatic clamoring continued during his extended sentence at the Marion, Illinois Penitentiary. He had become the editor for the prison newsletter. Dale had pitched on their softball team. He even joined the prison’s country band, “The Tear Drops.”

Dale consistently corresponded with his imprisoned accomplices, his lawyer, James D. Adams, as well as reporters. Many letters condemned the prison system and pushed for reform.

Accomplices

Morris Colosky, the helicopter hijacker, along with the get-a-way drivers were all sentenced to time behind bars.

Dale Otto Remling Released

Dale Otto Remling was released on September 13, 1993. He had moved to Bakersfield, California, north of Los Angels, where he lived until his passing at 71 years old in July 1999. His family laid his ashes to rest under a rock painted marked with his initials in the mountains where he could be free.

Eerily Electrifying

I found myself enamored with Dale Remling. It was as if I was under his charismatic spell. Not that I condone crime, but he definitely thought outside societal norms. I wish we could have interviewed him.

As we sat at The Crossroads Bar I pondered questions I would have asked Dale Otto Remling, the charismatic criminal. Thank you for coming along with us! Stay tuned for our video about Remling’s helicopter escape on YouTube!

Resources:

WFMK 99.1 article

MLive 2011 article

Find A Grave website

Experience Jackson article