that toddling town

 

Chicago has long been thought of as a hard drinking town, and the thirst of the natives made Al Capone a very wealthy man.

In 1922, a man named Paul Whiteman first recorded a song titled “That Toddling Town”, but versions have also been done by Tony Bennett, Lyle Lovett, Frank Sinatra, Perry Como, The Georgians, Benny Goodman, and several other artists.

Here’s the version by Old Blue Eyes:

Frank Sinatra - Chicago (That Toddlin' Town) - YouTube

Chicago is not the only town that became famous due to alcohol, and another one those towns is my old hometown of St. Paul, Minnesota.

During Prohibition, Chicago mobsters occasionally migrated to St. Paul when things got too intense in the Windy City.  The late 1920’s to the early 30’s was known as the gangster era in St. Paul.

St. Paul in the late 1920s and early 1930s was known as a “‘crooks’ haven”—a place for gangsters, bank robbers, and bootleggers from all over the Midwest to run their operations or to hide from the FBI. The concentration of local organized crime activity prompted reformers and crime reporters to call for a “cleanup” of the city in the mid-1930s.

St. Paul earned its reputation as the “sanctuary for criminals” in the Midwest with the help of corrupt politicians and police chiefs who agreed to turn a blind eye to gangsters’ underground activities, which included smuggling, racketeering, and gambling. This collaboration began in 1900 with the Layover Agreement, an unofficial contract between criminals and Chief of Police John O’Connor.

In exchange for tip-offs about FBI raids and protection during their “layover” in the city, the gangsters first agreed to check in with the St. Paul police when they were in town. Second, they gave a portion of their gains to the police department. Finally, they agreed to commit no crimes within the city limits, though Minneapolis was fair game. Police chiefs after O’Connor, such as Frank Sommer (1922–1923) and Thomas A. Brown (1930–1932), continued to use the “O’Connor System” in an effort to keep crime levels down in St. Paul and to profit from gangsters’ illegal operations.

The prohibition of alcohol from 1919 until 1933 also encouraged the rise of St. Paul as a center for gangsters’ activities. The Volstead Act (or the National Prohibition Act), introduced by Minnesota Congressman Andrew Volstead in 1919 and made part of the U.S. Constitution as the Eighteenth Amendment, banned the manufacturing, sale, and transportation of alcoholic beverages. The closing of breweries and distilleries resulted in the rise of bootlegging (the smuggling and illegal sale of alcohol), and St. Paul became known as one of the “wettest” cities in the nation. The prohibition of liquor also led to an increase in organized crime, since mobs and gangs controlled bootlegging operations.

Knowing that they were generally safe in St. Paul, notorious criminals—including bank robber John Dillinger and his girlfriend Evelyn Frechette; racketeer and mob leader Al “Scarface” Capone; and the outlawed duo Clyde Barrow and Bonnie Parker—stayed in the city at some point, though most of their crimes were committed in other Midwestern states. In 1932, however, more than 20 percent of the nation’s bank robberies took place in Minnesota.

Gangsters frequented favorite spots throughout the city, such as the Green Lantern Saloon on Wabasha Street and Nina Clifford’s brothel on Washington Street. Some gang leaders used St. Paul as the headquarters of their operations. Leon Gleckman, known as the “Bootlegging Boss” and the “Al Capone of St. Paul,” established the base of his bootlegging business at the St. Paul Hotel.

Alvin “Creepy” Karpis and the Barker family—the core members of the Barker‒Karpis gang—set up a home in West St. Paul. FBI director J. Edgar Hoover had his eye on the gang's members after they robbed a store in Missouri and killed a sheriff on December 19, 1931. Hoover targeted Katherine “Ma” Barker, the mother of two of them, as the leader. FBI files suggest, however, that she was not heavily involved in her sons’ activities. Former gang members later claimed that she tagged along to give the impression of a mother traveling with her sons. Nevertheless, Hoover helped establish Ma Barker’s reputation among FBI agents and the American public as the gang’s mastermind.

Although the Barker-Karpis gang selected St. Paul because it was calmer than other Midwestern cities, they did not stop their criminal activities. In 1932, the gang robbed the Northwestern National Bank and Trust Company in Minneapolis and later the prominent Third Northwestern National Bank.

Although they had close calls with an FBI raid, the gang was able to flee in time to Wisconsin, thanks to tip-offs from a friend with contacts in the St. Paul police department. The gang suspected that Ma Barker’s boyfriend, Arthur Dunlop, had spilled details of their successful heists to their landlady’s son. When the police arrived at their hide-out spot in Webster, Wisconsin, they only found Dunlop’s dead body on the shores of a nearby lake.

In 1933 and 1934, the gang returned to St. Paul to plan the kidnappings of wealthy St. Paul businessmen William Hamm Jr. (president of the Hamm Brewing Company) and Edward Bremer (president of the Commercial State Bank of St. Paul), in exchange for large ransoms. Both victims were released shortly after the gang received the ransoms. But the kidnappings showed signs of the O’Connor system breaking down, since these crimes had been committed inside the city of St. Paul. Federal and local efforts to track down the kidnappers intensified as the story grabbed national headlines, and the Karpis-Barker gang members began to doubt the reliability of their police connections.

Similar FBI hunts for gangsters throughout the Midwestern states dragged on for more than a decade, while reformers such as St. Paul police chief Thomas Dahill and Mayor Mark H. Gehan called for a “war on hoodlums.” In March 1934, Dillinger had a shootout with the police and the FBI at his St. Paul residence, the Lincoln Court Apartments. Although he managed to escape to his doctor’s clinic in Minneapolis to hide and to receive treatment for his wounds, newspaper coverage of the shootout and Dillinger’s escape convinced citizens that the city needed to be “cleaned up.” This incident also made St. Paul a target of federal and state law enforcement agencies when Hoover sent in FBI agents to search the city for evidence of Dillinger.

Dillinger and other “public enemies” fascinated the American public with their ability to survive shootouts and escape police raids. Some local Minnesota residents, however, such as the members of the St. Paul Women’s Club, acted to end the crime wave. They helped elect the reform-minded Mayor Gehan and alerted the FBI to sightings of gangsters. Other Midwestern residents made deals with the FBI, offering them information about gangsters’ whereabouts. This was how Dillinger was finally caught: with a tip-off from a woman who agreed to help capture him. When Dillinger emerged from the Biograph Theater in Chicago with two women (one of whom was the informant), FBI agents cornered him in an alley, shot him five times, and killed him.

After Dillinger’s death, a number of other gangsters were killed by the police or brought to trial for their crimes. In January 1935, Ma Barker and her son Fred were killed during a shootout with the FBI in Florida. In June 1935, Doc Barker and four other gang members were brought to trial at the St. Paul federal court for the kidnapping of Edward Bremer.

In May 1936, Hoover, who had been criticized by a senator for not making any arrests himself, claimed to have personally arrested Alvin Karpis. He brought Karpis to trial in St. Paul, where he was charged for his involvement in the Hamm and Bremer kidnappings. On August 3, 1936, Karpis pled guilty to all charges and received a life sentence in Alcatraz. The “gangster era,” with its sensationalized hunts for wanted criminals throughout the Midwest, was finally winding to a close.

 https://www.mnopedia.org/event/gangster-era-st-paul-1900-1936

 Decades before the gangster era, St. Paul’s existence came about due to the activities of a guy named “Pig’s Eye” Parrant, who was the first person of European descent to live in what is not the city of St. Paul.

https://en.wikipedia.org/wiki/Pierre_Parrant

Sources disagree about Parrant's exact history before settling in the Minnesota Territory, but most indicate that he was of French Canadian origin and born near Sault Ste. Marie, Ontario, around 1777. For most of his adult life Parrant made his living as a fur trapper while working for a company called McKenzie and Chouteau During his days as a fur trapper "Pig's Eye" Parrant, so called because he was blind in one eye, started to gain a somewhat dubious reputation with law enforcement, most likely due to his dabbling as a bootlegger With the onset of age and the fur trade's decline Parrant began seeking new endeavors to earn a living. His search brought him to a fledgling new settlement near a military outpost called Fort Snelling in the Minnesota Territory.

Arriving at Mendota in 1832, Parrant began to carve out a new life for himself while residing in a squatter's colony near Fort Snelling. His new career found him distilling liquor, which he sold to other squatters, the indigenous people of the area, and even the soldiers at the fort. This new business served "Pig's Eye"  until 1838, when the squatters were forced off the land surrounding the fort due to their strain on surrounding resources. It was at this time that the 60+-year-old Parrant made a claim on a tract of land at the entrance of what was known as Fountain Cave. This cave was situated on the east bank of the Mississippi River just upstream from what is now Downtown Saint Paul. Then, around June 1, 1838, Parrant completed a small shack that, according to an 1892 publication by Albert A. Jones, became "the first habitation, and the first business house of Saint Paul.

 

Fountain Cave was an excellent location for Parrant's claim, as the spring inside it provided a steady water supply for his still. It was at Fountain Cave that Parrant opened a tavern that became wildly popular with the surrounding community. The bar, known as "Pig's Eye" or "Pig's Eye Pandemonium", was easily accessible to local residents, riverboat crews working on the river, and the soldiers from nearby Fort Snelling. Parrant had become so popular, in fact, that when a nearby resident named Joseph R. Brown sent a letter to a friend in 1839 he gave the return address simply as "Pig's Eye." Not long after, Brown received correspondence at the address he had given. As a result, the growing community around Pierre's bar became known as "Pig's Eye." The city's name might have remained Pig's Eye had it not been for the arrival of a Catholic priest named Lucien Galtier. So aghast was Galtier that the village on the river derived its name from a man of such ill repute that, when he built his small chapel in the area in 1841, he reportedly stated, "Pig's Eye, converted thou shalt be, like Saul; Arise, and be, henceforth, Saint Paul!" It is disputed whether Galtier actually said those words, but the story is part of the city's folklore.

In 1844, Parrant lost his claim at Fountain Cave and was forced to vacate the land.

It is not clear why. Some sources indicate that he was involved in a border dispute with a neighbor; others say he was forced to sell his claim because of mounting debts. Despite the fact that the new settlement became known as St. Paul, the lake near where Parrant established his tavern is known, even today, as “Pig’s Eye lake.

 

No history of St. Paul would be complete without a murder mystery or two, and Gary Brueggeman gives us one in his book, “Minnesota’s Oldest Murder Mystery”, which covers the history of St. Paul prior to 1844, when Pig’s Eye Parrant was still in business.

 On September 27, 1839, the battered body of a middle-aged Irishman was found by some Dakota Indian boys. The corpse washed up along the Mississippi River shore, about seven miles downstream from Fort Snelling near the ancient Indian landmark the non-Indians called Carver's Cave.

It was the body of Sgt. John Hays, a popular former soldier, who, prior to his disappearance twenty-one days earlier, had been sharing a log shanty a few miles upriver from the cave with his friend and business partner, Edward Phelan (or Phalen). Before the year was over, Phelan was arrested and charged with the murder of his friend.

This is the first book to focus on this historic murder and the first thorough biography of Phelan, a notorious pioneer intimately involved in the making of St. Paul and founding of Minnesota. Was he guilty? All investigative reports and records of Phelan's trial were mysteriously lost and no newspapers covered the story. However, in 1994, St. Paul historian Gary Brueggemann made an amazing discovery in the Minnesota Historical Society archives: hidden in the papers of Joseph R. Brown was Brown's original Justice of the Peace casebook which included his handwritten transcription of the Hays' murder hearing.

Using this record, other primary sources, and drawing from decades of studying Minnesota and St. Paul history, the author theorizes a logical solution to Minnesota's oldest unsolved murder.

When I lived there, St. Paul was a clone of the Ozzie and Harriet years, but if you dig a little deeper, it’s past as the “toddling town” is impossible to miss.

https://www.amazon.com/Minnesotas-Oldest-Murder-Mystery-Unsaintly/dp/1592985351