How One Man’s Daring Prison Break Inspired Copycats in the Milan Prison

In the shadow of Michigan’s only successful aerial jailbreak, others plotted their own flights to freedom.

Image: Newspaper clipping of a scene from the 1975 movie “Breakout,” where Charles Bronson breaks Robert Duvall out of a Mexican prison with a helicopter. The movie was shown in theaters a week before Dale Remling’s escape using a helicopter. Image: The Herald-Palladium, June 7, 1975.

Dale Otto Remling’s audacious 1975 helicopter escape from Jackson Prison became the blueprint for a series of attempted copycat breakouts at the federal correctional facility in Milan, Michigan.

1975 Dale Remling’s Famed Aerial Prison Break

On June 24, 1975, Dale Otto Remling orchestrated Michigan’s only successful helicopter prison escape when he fled from the State Prison of Southern Michigan at Jackson. Remling, who was serving time for passing bad checks, arranged for a hijacked helicopter to land in the prison yard while inmates were exercising outside. The daring escape made headlines when the helicopter, piloted at knifepoint, touched down briefly to allow Remling to climb aboard before soaring away over the prison walls. The 43-year-old convict’s freedom was short-lived, however, as authorities captured him just 30 hours later in Leslie, Michigan, only about 15 miles from the prison. The spectacular jailbreak subsequently inspired multiple attempted helicopter escapes at Michigan prisons over the following decades, though none were successful, with FBI agents often posing as helicopter pilots to foil such plots at the federal correctional facility in Milan.

1976 Roger Fry

In September 1976, the FBI arrested four people, including two couples, for plotting to help California drug smuggler Roger Alstair Williams Fry escape from the Milan Federal Prison near Ann Arbor, Michigan. The elaborate plan involved using a helicopter to land on the prison baseball field at dawn, with armed accomplices shooting guards in the watchtower. An alternative plan included driving a bulletproof garbage truck through the prison fence.

The plot was uncovered when an FBI informant inside the prison revealed details about the operation. Two of the conspirators, Joan B. Pittman and Pauline Wehmeyer (Fry’s wife), were arrested on August 20, 1976, while crossing the U.S.-Mexico border carrying $10,000 in undeclared cash, allegedly intended to purchase a helicopter. The conspirators had visited Milan prison multiple times to plan the escape, even renting a Ford Pinto and bringing a camera to scout the location. Authorities noted that Fry was not placed under special security despite the plot being known, and two conspirators allegedly visited him to discuss the plan.

In a surprise epilogue, after a 10-week trial that concluded in December 1977, Fry was acquitted of both conspiracy to escape and conspiracy to murder a federal officer, charges that could have resulted in a life sentence. His defense attorney successfully argued that Fry had been entrapped by an FBI informant who secured his own freedom by providing information about the alleged plot. Although Fry was cleared of the escape charges, his three co-conspirators, including his wife who received a 30-month sentence, had previously pleaded guilty. Fry continued serving his 10-year sentence without parole at a maximum-security prison in Marion, Illinois, for running a criminal enterprise that smuggled approximately 115 tons of marijuana daily from Mexico to the United States.

1986 Eggleton Brothers

In November 1986, an undercover FBI agent posing as a helicopter pilot foiled an elaborate prison escape plan when the brother of convicted bank robber Gary Wayne Eggleton met with the agent at a restaurant in Adrian, Michigan. Eggleton, serving a 45-year sentence at the federal correctional institution in Milan for a 1983 St. Louis bank robbery and kidnapping, had planned an aerial escape from the prison’s compound area, which despite being surrounded by double fencing and concertina wire, contained large grassy areas where a helicopter could potentially land. Prison authorities discovered the plot in October and alerted the FBI, leading to John Eggleton’s arrest and charge of aiding and abetting conspiracy to assist an escape, while Gary Eggleton was charged with conspiracy to escape.

1988 William Carroll

In March 1988, the FBI foiled an elaborate helicopter escape plot by William Carroll, a 36-year-old counterfeiter serving a 15-year sentence at the federal prison in Milan, Michigan. Carroll had attempted to hire a helicopter pilot, offering $1.25 million in counterfeit money, but the FBI responded by sending an undercover agent posing as a pilot. When the helicopter appeared over the prison yard as arranged, Carroll waved a red apron as a signal but was left behind when the aircraft flew away, at which point he angrily returned to his cell block as guards emerged.

Carroll’s scheme involved secret letters written in lemon juice that revealed details when heated, including a prison layout with the landing spot marked, a description of what he would wear, and a “recipe” for counterfeiting money that required Jimmy Buffett tapes, a cassette player, marijuana, and St. Pauli Girl beer. He also requested high-powered rifles and semiautomatic handguns to be waiting in the helicopter. The FBI documented the entire failed escape attempt on videotape, after which Carroll was transferred to segregation and faced potential charges of attempted prison escape and plotting to murder a federal witness.

After running the article, the Sun Times News received the following letter from a former Milan FIC employee who recalled Carroll’s escape attempt and another:

I read with interest the Copycats article about Milan FCI.  I was the Landscape Officer, “Grounds Maintenance Lead Foreman” in Govt-Speak there from 1966 to 1992.  The staff really didn’t know much about security matters but for the Wm. Carroll one in 1988, I was a spectator.  After I turned my detail back inside the gates for lunch that day, I was told not to bring my detail or any inmate back out outside that afternoon.  They indicated to me there would be an escape attempt from the recreation yard by helicopter.  I took my landscape truck and parked it on the road outside the fence in front of the recreation area.  I thought I could provide additional radio support if needed.  The helicopter arrived and the inmate with a shirt or towel waved around and the copter came lower, then zoomed away.  A group of Officer’s immediately surrounded that inmate and whisked him away to the cell house.  It was exciting, but it made me think of a time early in my FCI career when I had to clean up the mess of an escaping inmate who had climbed to the roof at night and then, wearing two pair of gloves jumped into the top of the fence, slipped out of the gloves, and was free until he jumped up, just as the Tower Officer fired again.  The shot hit him and he fell dead.  It was my job to “clean up the mess before the press comes.”  I will always remember that day.

Ken Baumann, Milan

Sources: Detroit Free Press: September 29, 1976. December 8, 1977. November 14, 1986. March 9, 1988.