When Mansfield Was Little Chicago 1: The 1920s & 1930s

The era of the 1920s and ‘30s was a truly dynamic and fulfilling period of growth for Mansfield, as is clearly evident by the skyline itself which rose at that time to new heights.  Not all that spirited energy was aspiring upwards, however: a considerable amount of it went underground.

There were a number of decades in the history of Mansfield—several whole generations on the timeline—when the city was known in Ohio and around the nation as “Little Chicago.”

The implication was that Mansfield lived up to the lively reputation of Chicago as a hive of crime, vice and corruption.

It was a reputation not without merit.

There were plenty of other towns in the American Midwest who aspired to the title of Little Chicago, and each of them had its own litany of vices and public sins to recite in establishing their claim to the title.

But Mansfield has the rare distinction of having earned the title honestly—in paperwork filed by the Federal Government in the 1920s, and by the FBI in the 1930s.

1920s: Wheels

The dynamics of traffic into and out of Mansfield—so essential to the Little Chicago sensibility—made a dramatic shift in the 1920s when people were no longer dependent on railroad travel between cities because they began driving cars.  Those people needed good roads to roll on, and the first paved surface from NY to Chicago was the Lincoln Highway, which passed right through Mansfield and placed it prominently on the U.S. map.

Automobile traffic dramatically changed the complexity of crime, and the evolution of “interstate” mobility was the single key factor responsible for creating the FBI. 

In the 1920s and ‘30s, gangsters could suddenly flee a city without having to expose themselves in a public train station. 

A perfect example of this mobility took place in 1927 when a gang of gunmen from Toledo robbed a jewelry store in Lodi, stole a car and drove it to Shelby, where they stole a different car to drive to Galion, to knock over a filling station.  They took a Galion car to Mansfield where they snagged a brand-new Cadillac on Third Street so they could escape to Akron.  When the car turned up a few days later east of town on the side of the Lincoln Highway, it had over 2,000 miles on it.

With this new agility of road traffic, the crime networks all re-aligned, and North Central Ohio found itself vulnerable to Ohio big-city gangsters who had never before given the place much attention.

This Lincoln Highway sign on Ashland Hill in 1926 clearly establishes Mansfield within the greater context of United States culture and geography, as only 599 miles from New York.

1920s: Bottles & Votes

The other dynamic of public crime that made a dramatic surge in 1920 was sparked when Prohibition came into effect and alcohol was outlawed. The Mansfield Police Department—some still on horseback—suddenly had to deal with an army of rum runners, and city blocks full of speakeasies.

Not to mention gangsters from Toledo who thought Mansfield was an excellent market for bonded whiskey.

The Feds sent a special agent to town in 1921 who reported, after three weeks of secret investigation, that whiskey was easy to find in Mansfield.  In fact, any stranger could walk into a garage right behind the County Courthouse, or next to the City Jail, and walk out with a bottle. 

“It would be difficult,’ he wrote, “to stand in Central Park and shoot a sling shot in any direction without hitting a bootlegger.”

The News-Journal was increasingly alarmed by the flagrant abuse of Prohibition, as more out-of-town hoodlums were seen spending time in downtown.  The publisher mounted a public crusade to crack down on speakeasies by implicating public officials in print.

Shortly afterward the newspaper offices were bombed.   

The guy who threw the explosives was seen leaning out of a car with Toledo plates.  The blast, in addition to attempted intimidation of the press, represented a fierce escalation in a turf war playing out in Toledo.

That North Coast contest had a Detroit gang trying to muscle Toledo out of the booze business, and in their shooting match one of the pawns was Mansfield.  A minor ploy in their strategy involved the kidnaping of a local still operator and several midnight gangster raids in the woods around Lucas.

The game ended rather quickly with the assassination of a Toledo mob boss, and the dramatic racketeering trial that ensued was big news here.  Throughout it all, however, the top of the Mansfield chain of command kept their heads down and didn’t have anything to say.

The editor of the News-Journal lamented quite publicly how the city coddled “known criminals,” and the story was picked up by leading newspapers across the country.  After that, lots of known criminals from around the country made trips to Mansfield to see what the attraction was.

It wasn’t difficult for them to discover it for themselves.

Reporters located 200 places in downtown where a drink could be purchased by any stranger. When they interviewed a number of the bootlegging barkeeps, none of them would comment on the Mayor, but they all said they regularly contributed to his re-election campaign fund.

At 4:00 in the morning, the car sped past the Walnut Street side of the News-Journal building and tossed a bomb in that blew out all the windows and wrecked the mail room. Hours before, the editor had received a message that read, “Lay off or you’ll get yours.”

It was the fifth bombing of a Mansfield paper in five years, the second in this building. The New York Times front page headline read, RACKETEERS BOMB OHIO NEWSPAPER.

Finding the addresses of Mansfield speakeasies is not particularly difficult through newspaper records of Police raids, but finding the building still standing is very rare. This view of North Main from Third Street was taken in 1932 during the Little Chicago era.

Check out the distant background: the elevators made sure everyone downtown knew where they were.

North Main Street between the Erie Tracks and Sixth Street was a dense colony of bootleggers and speakeasies in the 1920s. Of the dozens of addresses seen in this photo only three remain today, including Creamers–the tallest building seen on the left.

The Vice Squad

While there is plenty of evidence to document Mansfield’s estimable reputation for illegal booze, the city was more truly renowned as Little Chicago because of its gambling.

The phrase they used to describe the city was wide open, which meant you didn’t have to go far to find action, and you didn’t need to lower your voice asking about it because it was no secret.

The town was such a famous den of gambling that the Governor of Ohio very specifically and very publicly directed Mansfield’s Mayor in 1925 to shut it all down, after his inspector found 42 places that sold Punch Boards, or sported Black Jack tables and dice games.  The actual report listed six city blocks where these enterprises were going on, and said it “represented only 25% of the total volume of criminal gambling in Mansfield.”

Accordingly, in March all the hotels, pool halls, cigar stores, barber shops, drug stores, dance halls, night clubs and brothels were raided.  The Mayor made a large headline speech publicly berating Mansfield pikers with a fierce scolding.

In three months, by June, the rebuke had worn off, and everyone was back to business as usual with Punch Boards and card games.

That’s how it worked in Mansfield: every few years—as there were new Mayors, new Police Chiefs, and new Ministers’ Associations—headlines announced a new “war on gambling.” 

Then all of the Punch Boards would be confiscated. 

Store owners down on the street level griped that these raids targeted only small-time petty pastime games, while one floor up there were high-stakes tables and slot machines all over downtown.

The easiest place to find casual gambling would be at one of the dozens of pool rooms or cigar stores, including the Manhattan Billiard Parlor on N. Park Street, seen here in 1927. The building still stands on the Square though it bears little resemblance to this shot.

These are authentic period Punch Boards from downtown Mansfield, found among the miscellanea left in the basement of City News & Suzy’s Smoke Room at 100 N. Main Street.
Customers paid for the chance to pull or push the circles to reveal a number beneath, which may or may not pay off.

A small sampling of headlines from the Mansfield News, the Mansfield Journal, and the Mansfield News-Journal from the 1920s to the ’50s.

A careful look at the background through the trees shows the front of a well-loved landmark on the Square for many decades: Schmutzler’s Cafe at 25 N. Park Street. While the street level lunch room was extremely popular from 1918 to 1966, it was a not-very-well-kept secret that upstairs had a high stakes crap game that ran for decades. It was raided a couple of times in the 1940s and ’50s for propriety’s sake. Directly across the Square was another not-very-carefully-kept secret: Mansfield’s premiere Bookie Joint.

The Cops

City administrations came and went during the Little Chicago era, with elected officials who were sometimes less interested in maintaining strict adherence to the law, but during those decades there was one constant force that stood as a stabilizing element for the community: the Men in Blue.

There was no question about their earnest enthusiasm for doing their job. 

One day in 1932 when a call came in that hold-up men were peeling out of Mt. Vernon headed north, two MPD officers grabbed a cruiser and sped south to meet them head-on.  The confrontation and chase actually took place ripping around the blocks of downtown Mansfield. It ended quite suddenly when Captain Bates raced up beside the getaway car and Patrolman Schuck leaned out his window and pointed a machine gun into the face of the driver.

It was recorded by MPD as the “most spectacular capture in Mansfield criminal history.”

Even as late as 1938 Mansfield Police Department had a traffic cop on horseback. This photo from 1924 was taken in front of the city jail on South Walnut Street.

The Little Chicago city scape as captured in 1931. All of these tall buildings went up within a span of six years from 1925 to 1931, changing the downtown from a small town to an actual city.

1930s: The Greystone

Witnessing the age of gangsters and Little Chicago in downtown Mansfield was a landmark dinner club called the Greystone.  It stood at the corner of North Walnut Street and the Lincoln Highway, so anyone from New York to Chicago might be in there to catch the show and down a steak.

I heard this from my friend Adelia who was in her nineties when she told it to me, but she was a recent graduate of Senior High in 1936 when it happened.

She loved the Greystone not only for the food, but the orchestra as well—that glowed like a black & white Manhattan romance movie with a wonderful dance floor.  The Nite Club atmosphere had the requisite cocktail comedy roles too, like the hatcheck girls, the cigarette girls, and a beautiful hostess in a flowing gown.

The Greystone also had a camera girl.  She would snap your souvenir photo and then deliver it to your table in a cute little folder.  Dee loved to have her picture taken anywhere, and flash bulbs were her favorite entertainment.

It was the flashbulb, however, that started a ruckus that night.

Like I said—like she said—you never knew who might be at the next table.  Whoever it was sitting behind her in the line of fire did definitely not want to be captured on film.

The men in the background—who were presumably wanting to not be noticed—made quite a noticeable scene about having their faces in a picture.

It was all very romantic to Dee.  She explained that in 1934 the Chief of Police had come to Senior High to instruct her classmates how to behave if they should ever witness a bank robbery.  He brought photos so they would know how to recognize the men who accompanied John Dillinger in his hold-ups. 

The Chief told them the FBI was enlisting their help personally—each and every one of them—in spotting bank robbers and killers.

She was sure these men at the Greystone were gangsters. 

After all, it was only the year before when the headlines said, Public Enemy No. 1 Seen In Mansfield! 

When Dee gave me the Greystone souvenir she told me to find out what the Most Wanted racketeers looked like in 1936 because they were probably in the photo behind her. 

Headlines in 1935.

The Greystone opened at the corner of Fourth & Walnut in 1936 in a city landmark built in the 1880s. Live entertainment kept the place busy until 1952 when it burned.
The tall building seen in the background is the News-Journal office pictured earlier in this article.

Among the sought-after memorabilia from Mansfield’s Little Chicago era are souvenir photos from the Greystone Nite Club.

Alvin Karpis was the last of the Public Enemy class before the FBI started calling them Most Wanted. After one of his kidnaping capers on the east coast in 1934, his car was being tracked westward and eventually spotted in Ohio, triggering a wild manhunt by local law enforcement. The car, seen above, was finally recovered just over the state line in Michigan, though any number of local folks claimed to have seen it on the roads of Richland County.

Mansfield was a perfect city for “Persons In Hiding,” during the Public Enemies years because it was small enough to be without regular FBI agents but large enough that a person could remain anonymous. After the Karpis sightings, the FBI was in regular contact with local law enforcement agencies, and often seen around downtown.

A Footnote:

Of all the research and notes I’ve ever collected on Little Chicago, and all the files I’ve paged through, and all the people I’ve talked with over the years, this is the one little piece of the story that always comes to mind first.

It came from a little kid.

Actually, it came from the mouth of an old man, but he was talking about what he remembered as a child growing up in Mansfield.

As a seven-year-old boy, Lloyd walked to Main Street every day with his big brother who was a shoe shine boy, and he saw plenty of men in suits with long coats and fedoras who all looked to him like guys in the movies.

That’s because in 1937 he and his brother went to the Madison Theater every Saturday all summer to watch the cliffhanger serial drama of Dick Tracy, and there didn’t look to be much difference between those gangsters on the screen and the cigar smoking mugs getting their shoes blacked in front of Siegenthaler’s.

To an adult, Lloyd’s story is not particularly logical, but kid-sense is made of a much more tenuous system of associations. So, imagine a little boy’s imagination and how easily it can conflate all these sensory perceptions:

a) what he overheard from grown-ups: the phrase ‘Little Chicago;” with

b) what he saw: Dick Tracy in movies that had skyscrapers in the background; with

c) what he witnessed every Saturday: heavy traffic and city skyscrapers on Park Avenue; with

d) what he believed: that MPD men in uniform he saw on the street might be some kind of badass movie stars.

He assumed that Little Chicago had to do with Dick Tracy because he had a small volume comic story, called a Big Little Book, in which Tracy’s life was all condensed down to pictures only a few inches tall.  Obviously ‘Chicago’ was some kind of code name for Mansfield.  And somehow the ‘Little’ aspect and the ‘Chicago’ aspect combined meant that Dick Tracy was here in Mansfield and there was every possibility that Lloyd might see him on the street.

So, he joined the Dick Tracy Secret Service Patrol and wore his button every time he set foot outside his home so that in case he ran into him, Dick Tracy would be sure to recognize Lloyd.

I love this story because, in its own way, it makes far more sense than all the facts I have gathered.  Vice and crime are adult things, and are, essentially, as far from sense as people can  go.  The kid’s world is a way more valuable use of one’s mind.

Thank You!

Images in this article come from the Mansfield Police Department, Anna Marie McCracken, Mark Hertzler, Suzy Saprano, Richland County Chapter Ohio Genealogical Society, Dee Hautzenroeder, John Baxter Black, Sherman Room of Mansfield/Richland County Public Library, Phil Stoodt, and some old man at the Library who pulled a picture out of his shirt pocket and handed it to me.


  1. Tim,

    my father, a musician, told me stories. He was playing music in the local night clubs and back in the day, was a member of the Greystone orchestra.

    He told me when heat was on in Chicago, Al Capone came to Mansfield. Dad said Capone hung out at the old Mifflin Inn, which burned down, and the Ringside. Even as a child I was in the Ringside often. I remember floorshows, that included very young children performing strip tease. Toni Bennett played the ringside as did other note able performers, I no longer recall their names. Louie Bromfield was a frequent customer.
    Btw Dad lost his instruments in the Ringside fire.

    He told me that Capone was always accompanied by several men. When those old cars would backfire The Capone guys grabbed their guns and the musicians hit the floor. I understand there was a tolerance of errant behavior, making Mansfield a Mecca for other gangsters to frequent the area. As a young person, Dad lived in the north end. When driving through that area, Dad would point out where bootleg was made, illegal gambling, prostitution, and other errant businesses were. I recall a woman, I think her name was Frieda, down on Sixth Street pushing a baby buggy full of bootleg her father and others made. she sold it to some of the local bars.

    Thanks for posting the article on Mansfield’s past. It is colorful. You keep the history alive. Thank you


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