Leon Gleckman: The Al Capone of Saint Paul

In the 1920s and ’30s, Saint Paul, the capital city of Minnesota, was known as a “crooks’ haven”—a sanctuary where bootleggers, bank robbers, and gangsters of all kinds from all over the Midwest came to hide out when the heat got too heavy in their home towns.   At one time or another the likes of  bank robber John Dillinger (1903-34, with his girlfriend Evelyn Frechette, 1907-69), mob leader Alphonse “Scarface” Capone (1899-1947), Alvin “Creepy” Karpis (1907-79), Kate “Ma” Barker (1873-35) and her boys, and the outlaw couple Clyde Barrow (1909-34) and Bonnie Parker (1910-34) spent down-time in Saint Paul under the protection of the chief of police, the sheriffs of Ramsey and Hennepin Counties (Saint Paul and Minneapolis respectively), the Twin Cities’ mayors, the county DA’s, other local officials, and the cities’ own gangster bosses.

When I first learned of this history, doing some research I didn’t know was connected to any of this, I had no idea that Minnesota even had a gangstedr past.  I wonder how many others are aware of this little sliver of American history.  New York, sure.  Chicago, no question.  Detroit, L.A., even Miami.  But Minneapolis-Saint Paul?

But it did.  And it had its gangster kings, too.  New York had Arthur “Dutch Schultz” Flegenheimer (1901-35) and Chicago had Al Capone.  Well, Minneapolis had Benny Haskell—and Saint Paul had Leon Gleckman, known, because of his control of the liquor business in the state capital, as “the Al Capone of Saint Paul” and “the Bootlegging Boss of Saint Paul.”  (An odd fact about the Minnesota gangster scene is that it was largely a Jewish mob.  Among many other Twin Cities hoods, both Haskell—his father was Haskell Zuckerman—and Gleckman were Jews.  Another of Gleckman’s sobriquets was “the Jewish Al Capone” and he was raised in a traidtionally observant Jewish home.)

Leon Gleckman was born in either Minsk, Byelorussia (now Belarus), or Brody, Ukraine, both then part of the Russian Empire, on 1 June in either 1893 or 1894 (records vary).  His family emigrated to the United States in the winter of 1903 (initially settling in Michigan, by way of London and Nova Scotia), and his father, Herman (that was his Americanized name; he was apparently born with the name Gershon), who started out as a rag-and-bone man with a horse and wagon, raised six children (a seventh child died in infancy) of which Leon was the third-born.  Leon married Rose Goldstein, daughter of Austrian and Russian immigrants, in 1913; the bride and groom were both 20 years old.   Herman Gleckman managed to accumulate some money, bought stocks and property, and prospered in the new land.

Leon Gleckman began working when he was very younng, selling flowers on the street.  He was a natural-born salesman, and eventually, he became a traveling salesman—but what he wanted was to go to law school.  He was something of an autodidact, however, writing poetry and spouting philosophy.  He began supplying Saint Paul with its illegal pleasures: booze, gambling, and prositutes. He set up his clandestine operation in the Hamm Building, a 1919 limestone, terra cotta, and brick six-story commercial building at 408 Saint Peter Street at 6th Street in Saint Paul; it was built by Williiam Hamm to house offices of the Theodore Hamm’s Brewing Company.  Gleckman’s St. Paul Recreation Company, comprising a billiard parlor, cigar stand, gym, boxing ring, and bowling alley, was in the basement.  The space also housed one of the city’s biggest illegal gambling operations, the foundation of Gleckman’s criminal empire; the legitimate activities made it difficult for city authorities to close the establishment—if anyone actually wanted to do that.  

Gleckman was doing all right purveying Saint Paul’s vices, but in 1920 Prohibition began across the country after the ratification on 16 January 1919 of the 18th Amendment.  (The Volstead Act, the law that athorized National Prohibition, passed Congress on 28 October and took effect on 17 January 1920.).  From that point on, Gleckman went into the boolegging business in earnest, supplying Saint Paul with another sinful pleasure, essentially cornering the market—with the chief of police running interference with both federal and state authorities and rival bootleggers.  (In 1930, Gleckman had enough influence  in city government to get Thomas Archibald “Big Tom” Brown, 1889-1959, appointed Chief of Police in Saint Paul.  To repay the debt, Big Tom, who stood 6’5", protected Gleckman’s rackets.)  He eventually had the Mill Creek Distilleries in Cuba to supply the Saint Paul speakeasies, and another distillery in the Virgin Islands.  General disdain for Prohibition among Saint Paulites boosted Gleckman—and Haskell across the river in Minneapolis—from mere bootleggers to important figures in their cities.  

Gleckman’s circle of “friends” didn’t just extend to gangsters, corrupt politicians, and crooked cops; he cultivated businessmen, bankers, and anybody with money or influence (preferrably both).  He was in contact with Thomas D. Schall (1878-1935), the state’s Republican junior senator, and Einar Hoidale (1870-1952), a  Democratic at-large Member of Congress from Minnesota.  By 1930, he insulated his family and his legitimate enterprises from his illegal activities by keeping suite 301-303 at the Saint Paul Hotel, the city’s luxury hotel at 350 Market Street, a three-minute walk from the Hamm Building.  This was where he conducted what he called “politics”: paying off police and city officials, as well as meeting with politicans and gangsters.  The FBI—just known as the Bureau of Investigation (BOI) until 1933, when it was renamed the Division of Investigation (DOI); it was named the Federal Bureau of Inestigation in 1935—called the Saint Paul “a rendezvous for gangsters,” and T-Man Michael “Mysterious Mike” Malone (1893-1960), who had previously infiltrated Al Capone’s syndicate in Chicago, also rented room 309 at the hotel to keep Gleckman’s visitors and activities under surveillance.

The bootlegger also had legitimate businesses: in 1927, Gleckman acquired a Cord-Auburn luxury auto dealership to go with his tire store, wallpaper store, and loan company (which doubled as a cash laundry).  But Leon Gleckman’s real buisiness, the source of his power in Saint Paul, was becoming more and more the running of a political machine.  With so much of Saint Paul’s administration on his payroll, he had become adept at getting his friends into important (and lucrative) positions in city government and law enforcement (like Tom Brown’s appointment as police chief).  He’d apparently inherited (or learned) his father’s talent for hondling—dealing—and turned it to fitting the right friendly peg into the right advantageous hole.  Gleckman was a macher—a fixer, a wheeler-dealer.  And he was good at it.  He “could fix a grand jury, buy off a judge, sheriff, or prosecuting attorney, secure a governor’s pardon for a convict, and ensure the appointment of a lenient police chief,” reports Paul Maccabee in his history of the time and place, John Dillinger Slept Here: A Crooks’ Tour of Crime and Corruption in St. Paul, 1920-1936 (Minnesota Historical Society Press, 1995).  He could also decide who would be a candidate for public office in Saint Paul, all the way up to city hall.  He was, in fact, in complete control of Saint Paul’s municipal government.

Average Saint Paulites saw Gleckman as a generous neighbor—he’s reported to have kept a jar on his desk for parking tickets people wanted fixed and they’d be picked up by a cop and never be heard about again; others with a taste for gaming, drink, and women of the evening found an accommodating pleasure provider; those who sought city jobs or needed help to negotiate the Saint Paul bureaucracy—cutting red tape, say, or smoorhing over a permit or licensing snag—knew him as a powerful advocate who knew where a lot of the bodies were buried.  (He may have known where they were buried, but he never planted any of them himself.  Gleckman probably caused a rub-out or two—we’ll hear about one likely instance—but he was not prone to violence, unlike his nickname’s sake.)  

By the late 1920s, at the height of his influence, Leon Gleckman ran Saint Paul without ever holding a city or county office.  He could get anyone he wanted a job on the municipal payroll—for his future son-in-law, when the younger man started dating Florence,  the oldest of Gleckman’s three daughters, in 1929, he got the 17-year-old a job trimming trees for the city.  (When the couple got engaged, Gleckman brought his daughrer’s fiancé into the Republic Finance Company.)  Of course, the flip side was that he could also block anyone from getting city work if he didn’t want them to.  

Then, on 5 December 1933, the 18th Amendment to the Constitution was repealed, ending Prohibition—and the wind went out of Leon Gleckman’s sails, as well as those of all other bootleggers in the U.S.  Booze was no longer illegal to make or sell, and Gleckman had to fall back on the other vices he purveyed.  Of course, his legit business were doing all right, having weathered the Great Depression (1929-39), at least until the Auburn Automobile Company ceased production in 1936.  

And he still ran Saint Paul.  Florence Gleckman called him “the man behind politics.”  “One time,” she recalled, Gleckman “had an argument with the editor of the St. Paul Pioneer Press.  Then the man had a vendetta against him.  They finally locked him up.”  In any case, he asserted that “he made more money through politically secured contracts than he ever made in the alcohol business.”  He even ruminated that “with the return of legalized liquor . . . and, having a large amount of money, [I] entered the political situation in St. Paul with the hope of some day becoming Mayor of St. Paul.”

But Gleckman’s power within Saint Paul wasn’t an impenetrable shield against legal troubles.  His first arrest came in August 1922 when revenuers raided his Minnesota Blueing Company, a front for an illegal distillery which the U.S. Department of the Treasury estimated was generating as much as $1 million a year (worth $14.25 million in 2018) from its 13 stills.  Gleckman was charged with liquor conspiracy, but the bootlegger remained free on bail for five years while the case was appealed.

In 1927, he was convicted of federal charges stemming from his illegal liquor business and sentenced to United States Penitentiary, Leavenworth, a maximum-security prison, for 18-months on charges of liquor conspiracy.  After six months or a year, the jailed bootlegger became a trusty because he was so well bahaved, assigned to work in the prison greenhouse, and then paroled.  Again in 1934, he was returned to Leavenworth for 18 months for income-tax evasion.  

In a footnote to history, Gleckman had the dubious distinction of being only the second man tried for federal tax evasion as a way to prosecute him for other crimes.  The first had been Capone in 1931, and the Department of Justice brought the same prosecutor who had tried Capone to Saint Paul from Chicago, U. S. Attorney George E. Q. Johnson (1874-1949).  Johnson had to try Gleckman twice to get a conviction, the jury having deadlocked the first time.  Leon Gleckman and his brother Alexander, known as “Jap,” had bribed a juror with $695 (about $13,000 today) to hold out for acquittal.  Later, there were also state and local charges for bribing the juror in the 1934 tax-evasion case, for which Gleckman served six months in the Minneapolis workhouse in 1938.  (Florence, who’d have been 25 at the time, recalled that he tried to break out.)   

In January 1940, Gleckman had also been convicted in New York in a bank-fraud case involving the Fort Greene National Bank in Brooklyn and sentenced to six months in federal prison.  According to no less an authority on the case than FBI director J. Edgar Hoover, “Strange things were going on in the” bank, whose “accounts were a maze of queer transactions.  Names of mysterious individuals of unknown address”—which included “two-time ex-convict and former czar of the underworld in St. Paul,” Leon Gleckman—“were found on notes running into hundreds of thousands.”  Gleckman and two confederates had been alleged to have defrauded the bank of over $250,000 (now worth about $4.4 million) by overstating the value of liquor stored in several warehouses.

Personal peril,  alongside legal consequences, was also a danger of Gleckman’s gangland life.  In what Maccabee dubbed the “occupational hazard common to bootleggers of the 1930s,” Leon Gleckman, the boss of Saint Paul, was kidnapped on 24 September 1931.  

Florence Gleckman recalled: “The summer before he was kidnapped, we had a cottage by the lake.  Mom [Rose Gleckman] kept saying the furniture’s been moved.  They sent her to a neurologist.  Afterwards, it turned out it had been the kidnappers.  They were going to take him from the lake, but he was never alone.”  If the recollection of the 18-year-old Miss Gleckman is correct, the kidnappers changed their plans.  The press record says that Gleckman was taken as he left his home at 2168 Sargent Avenue, forced to the side of the road by a car.  According to Florence’s account, “Leon liked to walk.  His office was downtown [at the finance company in the Merchants Bank Building at 332 Minnesota Street, seven miles away], he used to walk to work every day . . ., [and] he was kidnapped on his way to work.  A man in a corner house gave a signal when he walked by.”  

The Gleckman house was a whirl of gangsters, politicians, and ransom notes.  Florence also recounted, “One day Rose went to a fortune teller who said she saw him in a cabin, in the woods, by a lake playing cards.  Finally they paid the ransom.  When they got him back, it was true, he’d been in the North Woods.”  Indeed, when her father was released, after eight day’s of captivity, he’d been held in a cabin 40 miles from Woodruff, Wisconsin, 220 miles east of Saint Paul.  The kidnappers had demanded $200,000 (about $3 million today) but only $6,400 ($98,000) was paid—$5,000, plus whatever Gleckman had in his pockets, which turned out to be $1,450 (apparently, the kidnappers left their victim 50 bucks for cabfare).  Gleckman was released on 2 October and within days, one kidnapper had been killed, putatively by his confederates; four others had been arrested; and about 40 men and women had been jailed.  

(The Gleckman ransom money had been recovered, but it ended up in Big Tom Brown’s campaign chest for his run for Ramsey County sheriff.  Brown lost the race and in 1932, he was demoted to detective.  In 1936, he was permanently removed from the Saint Paul police force entirely.)

The identity of the person responsible for the whole plot was a matter of endless debate—and never successfully proved—but one popular candidate was Jack Peifer, a rival rum-runner of Gleckman’s.  Peifer had actually served as a go-between for the ransom money from Gleckman’s racket and the kidnappers holding him, but Brown and the Ramsey County attorney both warned the kidnapping suspects not to bring up Peifer’s name during their interrogations “if they knew what was good for them.”  When Gleckman was informed that some of the participants might be people he regarded as friends, he told the BOI he’d “take care of them his own way”—whatever that might portend!

For six months after the kidnapping, Gleckman had a 24-hour police guard outside his Sargent Avenue house.  Then, in the summer of 1932, Florence herself was taken for a ransom of  $50,000 ($850,000), which was never paid.  The young woman had just started studying at the University of Minnesota in Minneapolis.  Driving home from class one evening, she pulled in to park near her home and someone cut her off.  He had a blackjack in one hand and maybe a gun in the other.  He came up to the side of the car, according to Florence, and told her, “Do what I say and you won’t be hurt.”  The young man handcuffed her, took her glasses, and taped her eyes.  They went through a sewer and the man took her to the woods along the Mississippi River; the man left her tied up in the woods at night.  She was very scared, she said, and in the morning she started to cry.  “I’ll take you home,” the young man said.  He never hurt her.  The authorities never found him.

On Thursday, 15 June 1933, Jack Peifer was engaged once again in a high-profile kidnapping for ransom.  This time, he was in cahoots with the Barker-Karpis gang: Alvin Karpis, Ma Barker’s sons Arthur “Doc” Barker and Fred Barker, and a couple of hangers-on.  The gang had moved on from bank robbery to kidnapping as its principal criminal activity, having engaged in at least two previous abductions before taking Willam Hamm, Jr.  Hamm (1893-1970), son of William Hamm, Sr., who built the Hamm Building where Leon Gleckman had his gamblng parlor-cum-boxing gym-cum cigar stand-cum pool hall, et al., and grandson of the brewery’s founder, Theodore Hamm, was grabbed off the street in Saint Paul in the middle of the day by Karpis and Doc Berker who put him into a car driven by a third man.  

Hamm was made to sign four ransom notes in the amount of $100,000 (about $1.9 million in 2018).  Eventually, Hamm, who had succeeded his father as president of Hamm’s Brewing in 1931, was kept at a house in northern Minnesota by five or six men.  He was held until Sunday, 18 June, when he was driven after dark to Wyoming, Minnesota, and left on a highway.  Early the following morning, Hamm called his family and shortly, police arrived and took him home.  

All the perpeterators were apprehended or killed eventually, but not before they engineered one last kidnapping: Edward Bremer (1897-1965), son of Adolph Bremer, the major stockholder in the Jacob Schmidt Brewing Company, another Saint Paul beermaker, on 17 January 1934.  The gang asked for $200,000 ($3.7 million), but police and DOI speculated that there was also a more personal motive for the abuction.  It seems that the Bremers had cooperated with bootleggers during Prohibition, making beer on the QT which the bootleggers distributed, surviving when other liquor manufacturers suffered.  When the 18th Amendment was repealed, Schmidt Brewing severed its ties to the criminals, angering their former associates enough to prompt some to take revenge.  Bremer was generally not a popular man, even to members of his family.  

Of the main gang members, Doc Barker was arrested in 1935 and Karpis in 1936; Fred Barker was killed, along with his mother, in a 1935 shootout with the FBI; other members of the gang met similar fates.  (Historical footnote: after Alvin Karpis pleaded guilty to kidnapping, he was sent to prison on Alcatraz Island, the federal prison in San Francisco Bay.  He was paroled in 1969, becoming the rock’s longest-serving prisoner.  Doc Barker was also sentenced to Alcatraz, but he was shot during an escape attempt in 1939.)

Big Tom Brown also paid consequences, obliquely related to the kidnappings.  During the investigatons of the several Saint Paul abductions, the feds suspected that Brown had leaked information to the kidnappers.  He was removed from the investigation team and after further probing, the DOI determined that Brown had been involved in the kidnappings themselves.  He was dismissed from the Saint Paul police force on 9 October 1936, though he was never successfully prosecuted for his corruption.  The former police chief moved away from Saint Paul and, ironically (given his long association with bootleggers) opened a liquor store.  He stayed in that trade for some years, but was later arrested for non-payment of his taxes (a little like Gleckman and Capone) and for selling liquor without a license (also a sort of pale imitation of Gleckman and other bootleggers).  Brown was sentenced to a year in jail for these offenses but the punishment was suspended.  He died of a heart attack in 1959 at 69.

Leon Gleckman, the bootlegging kingpin and political boss of Saint Paul, also didn’t end well.  He died on 14 July 1941 in a one-car accident.  He was 48 years old.  The St. Paul Dispatch of that date reported:

Gleckman was killed when his west-bound automobile crashed at 1:50 a.m. into a pillar supporting the Union Depot concourse across Kellogg [B]lvd.  He died in a police ambulance en route to Ancker [H]ospital.

According to the Dispatch, Gleckman had played golf the afternoon before and then spent the evening with friends at the golf club.  He was apparently driving home and, the police believed, may have fallen asleep at the wheel.  Gleckman’s blood-alcohol level was .23, the equivalent of having had nine drinks of 90-proof liquor.  Geckman’s Chevrolet hit the abutment of the Saint Paul railroad station concourse so hard that the hood and steering wheel were crushed.  A night watchman at the Union Depot Company, who heard the crash, reported that he hadn’t heard any sounds of brakes or skidding tires.  The police didn’t find any skid marks, either.  

Gleckman died of a fractured skull.  The death was declared “probably accidental,” but privately, many people, incuding Gleckman’s family, beleved he’d committed suicide.  One cop stated: “You can’t prove it, but in my heart as a policeman, I think [he] wanted to do himself in.  We all think Leon killed himself. . . .  He was due to go to federal prison.  He was the king of the bootleggers and he didn’t fancy sitting in the Can.”

Gleckman, a notorious—and, apparently, beloved—figure in the Saint Paul underworld of the 1920s and ’30s, never made it to law school and never ran for mayor.  He was, nevertheless, the chief executive of Saint Paul, at least de facto, for the years of Prohibition, 1929 to 1933—and for several years thereafter.  Something of a dandy and a man-about-town, he was judged to have been highly intelligent and insightful, with an extraordinary problem-solving acumen.  In the early 1990s, when Florence wrote down some of her memories for her son, she noted that the name Gleckman was still in the phonebook, and she wrote: “People still call to say thanks for sending me to college, all kinds of stories, everybody loved him.”  According to Florence, her father had started the Republic Finance Company because he was always lending money, helping people out.  Even his prison file  characterized him as “self-confident, glib, and respectful.” 

A musical play, Last Hooch at the Hollyhocks by Lance Belville, was presented by the Great North American History Theatre and performed at the Minnesota Arts and Science Center in Saint Paul in 1990.  It featured Leon Gleckman as a character (the Hollyhocks was Saint Paul’s spiffiest speakeasy, owned by Jack Peifer), and one of Florence’s younger sisters attended a performance.  There’s also the Eagle Street Grille, a local restauant that features “a mob-themed menu” with interesting names for the menu items.  (There used to be sandwiches and platters named for the gangsters who lived or visited the city, including Gleckman, but that no longer seems to be true.)  Even the Saint Paul Hotel invokes its gangster history on its website and tells about Gleckman’s residency there.

[I wrote above that I learned about this history when I was researching another topic.  That subject was Leonardo Shapiro, the avant-garde theater director about whom I’ve blogged many times now, and I was researching his childhood and early family life.  You see, Leon Gleckman was Shapiro’s grandfather  and Florence, née Gleckman, was his mother.  Born Leo Richard Shapiro (he adopted the name Leonardo when he was in high school in homage to Leonardo da Vinci, whom he admired), the director-to-be was named after his grandfather, whom he never knew as Gleckman died 4½ years before Shapiro was born.  He nevertheless felt a special connection with Gleckman because both men were largely self-educated, an achievement Shaprio esteemed, and they both loved and wrote poetry.  (Shapiro had started out to be a poet before turning to theater.)  Shapiro once confided to me that Arthur Miller’s Death of a Salesman held special meaning for him; it may have been significant to Shapiro that Willy Loman’s death, also a suicide, was nearly identical to Gleckman’s.]