Gangster John Dillinger Escaped the Heat (and Cooled His Heels) in the Straits of Mackinac Prior to Chicago Shooting Death

The Great Lake region is rich with gangster history, steeped in the Prohibition era of the 1920s and early 1930s. Of course, when one things of mafia leaders, Al Capone immediately comes to mind. But, another leader in underground crime was John Herbert Dillinger (born June 22, 1903 in the Oak Hill section of Indianapolis)…who apparently fled to the Straits of Mackinac (specifically, to Bois Blanc Island in northern Lake Huron, about a dozen miles east of Mackinaw City).

Bois Blanc Island (sometimes referred to as Boblo Island despite complaints from people downstate who are familiar with the Boblo Island Amusement Park in Bois Blanc, Canada, in the Detroit River) is an island in Lake Huron in the southernmost part of Mackinac County. At about 34-square miles, the island is 12 miles long and six miles long.

According to a blog post on, it is “alleged that a cabin hidden deep in the woods of Bois Blanc had once been the hideout of none other than Public Enemy Number One, notorious Chicago gangster John Dillinger. As the story goes, John Dillinger underwent plastic surgery in 1934 to disguise his identity and evade capture, and while he was recovering from this surgery he hid out for several months in a log cabin somewhere in northern Michigan.’ Local tell maintains that this hideout was in fact situated on Bois Blanc Island itself, at the eastern extent of Twin Lake, where the ruins of three log cabins are still visible today.”

Although the writer won’t disclose exactly where the remains of the hideout are located, it is noted that it is “covered in moss in a shaded glen of spruces next to a cedar swamp.”

The blog goes on to say “that if there was any truth to Dillinger’s residence on Bois Blanc, those living on the island at that time have taken the secret to their graves, as island people are naturally reticent, and loathe to meddle in the affairs of others. Another factor was the bootlegging trade, in which many islanders had allegedly been complicit. During Prohibition, there was money to be made in moving illegal booze, and many otherwise legitimate folk had a hand in keeping the spigot flowing, especially if they already made their living on the water, and needed to make ends meet. Why would they rat-out Dillinger if it would bring the attention of the law to their island and potentially to their own less-than-legal actions? Not to mention the mob might take its own retribution upon anyone who snitched on them.”

FBI records note that “Dillinger, whose name once dominated the headlines, was a notorious and vicious thief. From September 1933 until July 1934, he and his violent gang terrorized the Midwest, killing 10 men, wounding 7 others, robbing banks and police arsenals, and staging 3 jail breaks—killing a sheriff during one and wounding 2 guards in another.”

Dillinger was shot and killed in an alley next to the Biograph Theater in Chicago on the evening of July 22, 1934. This past summer, 85 years after Dillinger was buried in a family plot at the Crown Hill Cemetery in Indianapolis, his nephew and niece (Mike and Carol Thompson) have filed a permit with the Indiana State Department of Health to exhume the body. They question whether the person shot on that infamous day in Chicago (and subsequently buried in Indiana) is in fact the notorious gangster and they want to conduct DNA testing to determine the actual identity of the body. The state approved the request, but the cemetery is fighting it to preserve the integrity of the site. A court battle continues…

For more about rum running, gangsters and Prohibition in the Straits of Mackinac, read “Mackinaw City at the Heart of Northern Michigan Rum Running” by author Russell M. Magnaghi.



Mackinaw City at the Heart of Northern Michigan Rum Running

The 110-foot USRC Mackinac, later USCGC Mackinac, was built in Baltimore, MD in 1903. It was stationed in Sault Ste. Marie and served the United States Revenue Cutter Service from 1903 to 1915 and in the United States Coast Guard from 1915 to 1917 and again from 1919 to 1939, patrolling the Straits of Mackinac for rum running. 

By Russell M. Magnaghi

Today as you stand on the south shore of the Straits of Mackinac looking at the iconic bridge spanning the Straits, you can hardly imagine the activity on water and land as people sought to evade the national Prohibition law. Passed by popular vote in Michigan in May 1918, the amendment to the U.S. Constitution went into effect in 1920.

At the time Mackinaw City was a tourist destination lined with resorts. The summer resorters wanted refreshment and thus provided a market for local bootleggers or distillers. Illegal liquor was made locally within Mackinaw City, neighboring towns and on farms. Since the economy was poor at the time this was an easy way to bring in cash. Stills popped up in every hidden spot. Although the newly formed Michigan Constabulary, later known as the State Police, tried their best to end the business it was a losing proposition. The liquor poured through the countryside. The Bootlegger House at 212 Jamet was home to a widow who supported her family by selling illegal liquor out of the house.

To the north was Canada where liquor literally poured into the United States. Again private individuals with fast speedboats picked up the liquor, many times aided by young Coast Guardsmen, brought it through the labyrinth waterways of the St. Mary’s River. Mackinac Island, across the Straits from Mackinaw City, was the staging area. Liquor reached the Grand Hotel much to the delight of guests who also enjoyed gambling. Liquor landed at the island was then shipped south to Capone in Chicago and to the Purple Gang in Detroit. However Mackinaw City was the terminus of the notorious Purple Gang’s run running highway north.

Across the Straits at St. Ignace, a fellow known as Black Jack was an outlet for Canadian rye whiskey. He operated quietly using his home as a front selling maple syrup. When raided at one point by Treasury agents they wanted to know who would buy 36 bottles of maple syrup? Black Jack naturally had no idea except that they were eating piles of pancakes.

On the Straits boats plied their illegal cargoes. Sometimes coal caring boats had liquor stored in sacks beneath the coal. At one point in May 1928 the Coast Guard chased the Geronimo loaded with 4,000 cases of liquor worth $250,000 on its way to Chicago. It was in the wee hours of the morning and the captain thought either he could outrun the cutter or he would be lost in the mist. The captain refused to stop; the Coast Guard fired a warning shot, and then disabled the vessel west of the straits. Two years later it was seized again, this time loaded with $600,000 worth of booze. The placid and magnificent Straits was busy during the era of Prohibition.

For those seeking bars and restaurants with Prohibition connections within a short drive (or boat ride) from Mackinaw City should check The Antler’s in Sault Ste. Marie, which was an ice cream parlor but never ordered a gallon of ice cream; Horn’s Bar and Restaurant on Mackinac Island, which had an ice cream parlor on the first floor and a speakeasy on the second floor, and Hessel E.J. Mertaugh Boat Works in Hessel, which once sold fast speed boats that brought liquor from Canada.


Russell Magnaghi, noted and award-winning historian of Michigan’s Upper Peninsula, is the author of “Prohibition in the Upper Peninsula: Booze & Bootleggers on the Border” published in 2017 by The History Press. He is a graduate of the University of San Francisco and St. Louis University, and retired from Northern Michigan University after teaching for 45 years.