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Growing up in jail with notorious 1930s gangster Hamilton on the run

Shirley Welsh Howie was nine-years-old when her father became Chippewa County Sheriff, moving his family into the jail in 1933

Shirley Welsh Howie was nine-years-old when her family moved into the sheriff’s residence of the Chippewa County Jail in January of 1933. 

Howie’s father was none other than Sheriff Willard Welsh.

Welsh supervised county law enforcement up until 1942 when he took over as Sault Ste. Marie Police Chief. Welsh served the city as chief until his retirement in ‘59.    

Howie had many stories to share about growing up in jail during the Great Depression.

Prohibition was just coming to an end, and notorious American gangster John Hamilton was hot on the run after committing a multitude of bank robberies and killing a police officer in Chicago.

“One night, dinner was over and the kitchen cleaned up,” Howie said. “Mom (Pearl) and we children (Howie, Jack, Anne, and Richard) were in the living room. I heard a noise in the kitchen and went to investigate. There were men coming from dad's office through the short hall and into the kitchen and a side entrance, entering cars which were parked beside the house. Some were carrying large rifles and others machine guns. I rushed back… mom came to check.” 

Howie later learned that her dad had received a tip from the neighbor of Hamilton’s sister, Mrs. Anna Steve of Algonquin, Sault Ste. Marie, MI. 

“Mother later stated that she never came as close to fainting as when dad kissed her as he was leaving, and she could feel his bullet-proof vest,” Howie said, remembering the night her dad left the house with federal agents sent by J. Edgar Hoover.

According to Sault Ste. Marie Public Library archives in an article published by Soo Today, entitled, “The 'Dillinger' gangster who grew up across the river – part 1,” Hamilton was born in 1898 in Byng Inlet, Ontario. His family moved across the St. Marys during early childhood, where he became known as “Red” for having red hair and “Three-Fingered Jack” after losing parts of his right middle and index fingers in a prank involving a sled and speeding freight train. 

Hamilton married Mary Stevenson in 1921 and lived with her on Elizabeth Street.

He worked as a carpenter back then. It was a respectable but short lived life. Prohibition went into effect a year prior,  preventing the manufacturing, sales, and transportation of alcohol across the United States. Rum-running over the border from Canada meant extra cash.

Hamilton was arrested for bootlegging in Detroit in 1924, but skipped out on paying his fine only to live a life of crime comparable to a classic Hollywood western.  

He and his wife’s brothers formed the “Stevenson Gang.”

Hamilton committed his first robbery on July 25, 1925. The outlaws made off with approximately $33,000 from the Lakey Foundry Corporation’s payroll in Muskegon Heights, Michigan. Then, in 1927, they robbed a Grand Rapids bank for approximately $25,000.

Hamilton was captured on March 15, 1927, following a failed bank robbery in South Bend, Indiana.

Hamilton confessed, but was also incriminated on charges in the Grand Rapids robbery. He was sentenced to 25 years at the Indiana State Penitentiary in Michigan City.

His wife divorced him in October of 1928. Court records cite “extreme cruelty and non-support” of her and their two children.

Hamilton connected with infamous bank robber Harry Pierpont in prison, later joined by Dillinger in 1929.

Pierpont had met Dillinger at Pendleton Prison in Indiana. Hamilton and Pierpont taught Dillinger everything he needed to know about robbing banks. 

Dillinger paroled, with instructions to rob a series of banks to fund a prison break. He, reportedly, carried out 10 bank heists in five states over a short period of three weeks.

Dillinger snuck firearms into the penitentiary, and the Pierpont gang waltzed out of the prison’s main entrance. They stole a sheriff’s car and took a deputy at gunpoint.

Dillinger was arrested and thrown into the Allen County Jail in Lima, Ohio on October 19th of that same year. Hamilton, Pierpont and others busted him out of jail, killing a sheriff in the process.

They stole firearms from two police stations, and Chicago became their home base. In the midst of the Great Depression, banks were widely distrusted and disliked by some citizens. This only granted the gang great public fame. 

On April 17, 1934 while on the run for various bank robberies, as well as the death of a cop in Chicago, Hamilton visited his sister – Mrs. Anna Steve of Algonquin, Sault Ste. Marie, Michigan. He brought Dillinger along with him.

“The federal Bureau of Investigations (FBI) had not been formed yet,” Howie said. “It was established by J. Edgar Hoover on July 26, 1908.”

The Bureau of Investigation (BOI/BI), along with Howie’s dad and other members of law enforcement, raided Steve’s house on April 17, 1934. 

“When they got to the house, they weren’t there,” Howie said. “Hamilton’s sister was arrested for hiding them.”

Steve and her son were both charged with harboring fugitives. Welsh returned home to his family, safe and sound.  

“I remember seeing Hamilton and Dillinger’s car covered in bullet holes,” Howie said. 

While on vacation in a rural Wisconsin Lodge called Little Bohemia, the BOI shot up a building occupied by the gangsters. A bystander and government agent lost their lives. Only the wives and girlfriends of the gangsters were arrested. 

All law enforcement agencies were on the hunt for Hamilton, who was allegedly seriously wounded by police. But the gangsters stole another car and headed into Chicago to seek medical attention.

It was reported that the Chicago underworld had barred doctors from tending to Hamilton’s gunshot wounds. He was then taken to Aurora, Illinois where Dillinger claimed his friend had succumbed to the injuries sustained.  

Additional Sault Ste. Marie Public Library archives published by Soo Today state that Dillinger was shot in a hail of gunfire in front of the Biograph Theatre in Chicago.

The BOI uncovered what was said to be Hamilton’s body in Oswego, Illinois on Aug. 28, 1935.

The book, “Running With Dillinger: The story of Red Hamilton and other Forgotten Canadian Outlaws,” written by Edward Butts points out various discrepancies in that story.  It even tells of the recollections of great-nephew Bruce Hamilton, who claims Hamiton survived his gunshot wounds and retreated to a long life in the Canadian wilderness. There may be no telling what actually happened to Hamiton. 

Howie also remembered the months leading up to the end of prohibition on Dec. 5, 1933. 

“There was a raid on a Saturday night,” Howie said. “Dad left and we didn’t know when he would be back.”

As usual, Mrs. Welsh distracted her children with games so that they would not be afraid. Howie said she was rarely fearful. She trusted her dad knew his job, and that the inmates were separated by a thick wall. 

“The sheriff's family residence was attached to the sheriff's office and jail,” Howie said. “It consisted of a large kitchen and eating area, dining room and living room on the main floor, three bedrooms and bath located on the second floor, and a third floor with a juvenile cell and extra bedroom. The jail building and the courthouse were the main buildings on a large city block; a cement black garage with four double doors between the jail and Courthouse, plus a fenced-in area behind the jail, used for an exercise area for the prisoners, completed the scene.”

Mrs. Welsh was the "jail matron," tasked with cooking for the inmates. She would serve food through a small food slot on the kitchen wall.

“You did not go into the kitchen,” Howie said, recalling large kettles filled with enough hot soup to feed up to 27 inmates at a time. “Each morning, mom would call in her grocery order to the Soo Co-op. There was a side door off of the kitchen store room, onto an enclosed porch where these deliveries were made. In the store room, there was a large tin bin probably 3’x3’x3' with a lift-up lid, where the bread was delivered each day from the bakery.”

Howie recalled sharing most family meals with extended family, borders, and jail employees. 

“That is what people did back then during the Depression,” Howie said. “They rented rooms and that is how they lived.” 

In her free time, she enjoyed much of the same privileges as other children in the neighborhood. She and her siblings had friends over. She roller skated around the courthouse and played in all of the colorful leaves from all the maple trees that once lived on the property.  

“I learned to drive when we lived at the jail,” Howie said. “Dad would place the car headed toward the fence in the parking lot. In those days, one had to shift gears going from first to second to third. Then, there was the reverse. I would put the car in first, drive past the fence, turn south to the sidewalk on Spruce, put it in reverse and back up to the starting spot.”

Once Howie obtained her driver’s license and the freedoms it brought, she learned to dread the courthouse clock. 

“I swear, I broke the three-minute mile – or was it the two-minute mile – whatever many was the night my foot hit the bottom step of 207 East Spruce before that damn clock dinged 11 p.m., my curfew,” Howie remembered. “Mom and dad didn't have to be up early. They could lay in the darkness and hear the clock.”

Howie graduated from Sault Area High School in ‘41, a few months after America had entered World War II in December. Many men were sent off to war. Howie left the jail for Cleary Business College in Ypsilanti that fall. She went on to work as a clerk for the FBI from 1943 to '45.  

In November of 1942 Howie was involved in an automobile accident. She spent three months in the hospital and returned home to the Sault. The streets were occupied by soldiers defending the Soo Locks. 

“A Sault girl did not go out with a soldier,” Howie said with a sly grin. “I was asked to go to a dance, so I asked my dad for 10 cents. I decided I wasn’t going to go, so he gave me 25 cents to get an ice cream sundae.”

Yet, Howie fell in love with and married a soldier of her own in 1945 – Matthew Howie. Together, they had four children, eight grandchildren, and a present total of 17 great-grandchildren.

Reviewing her own childhood as the daughter of the Chippewa County Sheriff during the days of Prohibition, Dillinger, and Hamilton, Howie had this to say: “There were exciting times; there were funny times; there were lonely times. I never wanted to be a matron. I don’t know how mom did it.”          

At 99-years-old, Howie remains sharp as a tack. She has written about her childhood in an article called, "My Time in Jail (1933-1942), published in the March edition of the Chippewa County Historical Society “River Surroundings” newsletter:

“We all grew up somewhere and if you spent your favorite days in Sault Ste. Marie, we would like to hear your stories. Dee Stevens has been running articles about Sault Ste. Marie's little communities for several years, and the historical society is hoping to pull all of the columns into a volume with photos, but we need some memories and personal stories!”