Capone-Adjacent Guys and Shady Land Deals


On July 10, 1922, Catherine Hoffman found herself facing a federal lawsuit.1 The United States government said alcohol was being sold on a piece of property she owned, at the northwest corner of Lawrence Avenue and Broadway in Chicago—the premises known as Green Mill Gardens. It didn’t matter whether Hoffman was selling any booze herself. In the eyes of the federal prosecutors, her ownership of the land made her responsible for what was going on there.

Hoffman was the only surviving child of Charles E. “Pop” Morse, who’d opened the first saloon at this location in 1897.2 After inheriting the property when her father died in 1908,3 she’d started leasing it to in 1910 to Tom Chamales,4 who tore down Pop’s old roadhouse and built Green Mill Gardens in 1914. Although Chamales financed and built the structure, turning it into one of Chicago’s most popular nightspots, he would have to hand over the keys to Hoffman when the lease ended in 1938. The property was still hers.5 And the land just west of the building—the outdoor space where Green Mill Gardens’ guests drank and danced on summer nights—belonged to Hoffman’s husband, Charles.6

By 1922, Chamales was required to pay the Hoffmans a monthly rent of $916.67 (roughly $17,100 in today’s money). That amounted to $11,000 a year (or $205,000 in 2024 dollars).7 The Hoffmans, who lived at 4901 North Glenwood Avenue, a few blocks northwest of Green Mill Gardens,8 said the rent from Chamales was their only source of income.

In 1922, they found themselves unable to pay a $240,000 mortgage and $38,000 in other debts they owed on the property. 9 As the Hoffmans told the story, their “financial condition was very bad.”10

Catherine, who was 39 years old in 1922,11 portrayed herself as naïve in business affairs. “This woman was unacquainted with business,” a lawyer for her said. “She never handled property.”12

According to the Hoffmans, Chamales had repeatedly tried to get out his lease and acquire the property. Over the years, he’d proposed various deals to the Hoffmans. They’d rejected all of these offers.13

A turning point came in July 1922, when the U.S. government filed that civil lawsuit, seeking to shut down Green Mill Gardens. At the same time, prosecutors filed criminal charges against Chamales and the man he employed as the venue’s manager, Henry Horn.

The way the Hoffmans later told the story, prohibition laws were hurting business at Green Mill Gardens. Chamales could no longer sell liquor, which had been a major source of revenue. As a result, the money generated by Green Mill Gardens “was barely sufficient to pay the rent as provided in the lease.”14

Catherine Hoffman denied having anything to do with selling alcohol. In a document filed in court, she said had “no knowledge of her own … that there is now existing or was existing …  any public or common nuisance, as defined by the National Prohibition Act or Volstead Act.”15

Around the same time Hoffman and the others were sued by the feds, someone showed up and offered to help her out with her financial difficulties.

Otto L. Annoreno. Broad Ax, April 8, 1922.

Otto L. Annoreno was a 40-year-old16 immigrant from Sicily,17 who lived at 6002 North Winthrop Avenue in the Edgewater neighborhood.18

Annoreno had started working in Chicago’s South Water Street produce and fruit market when he was nine years old, eventually becoming the vice president of a commission merchant business at the market, F.E. Nellis & Company. According to a 1922 newspaper article, Annoreno was “considered one of the most enterprising and successful men in the produce business.”19 As 1922 began, he was elected as the vice president of the city’s Italian Chamber of Commerce, known in Italian as La Camera di Commercio Italiana di Chicago. He also became one of the chamber’s “consiglieri,” meaning “counselors.”20

Annoreno was also a member of the Unione Siciliana, a fraternal and benevolent organization whose leaders were linked to organized crime. The Genna gang and Johnny Torrio had close ties with Unione leader Mike Merlo. At this time in 1922, Al Capone was a member of Torrio’s gang, still unknown to the public at large, but as he rose to power, he would take control of the Unione Siciliana in late 1925, according to historian John J. Binder.21 But Annoreno’s membership in the Unione Siciliana doesn’t necessarily mean he was involved with these gangsters. Inside the organization, law-abiding Sicilian Americans were struggling for power with the criminals, as they tried to clean up the group’s unsavory reputation.22

Annoreno seemed to be known as just such a law-abiding businessman. I haven’t found any newspaper articles or other documents pointing to his involvement in any crimes. He did have cousins who were mobsters affiliated with Al Capone, but it’s unknown how close of a relationship he had with them.

Joseph Annerino. Chicago Daily Tribune, November 23, 1928.

The most notorious was Joseph Annerino, better known as Joseph “Peppi” Genero. Otto and Joseph were both immigrants from the town of Termini Imerese, near Palermo, so it’s possible they knew each other. Their paternal grandfathers (who’d spelled the surname Iannarino) were brothers, making Otto and Joseph second cousins.23

The Tribune described Joseph as a “Capone lieutenant who was always ready to turn a few dollars in alcohol peddling, gambling, or conducting houses of ill fame.” He would be charged with murder and kidnapping, but never convicted, before being shot down himself.24 Joseph and his brother John Genero later became suspects in the St. Valentine’s Day massacre.25 Another Annerino/Genero brother, Thomas, was convicted in 1922 and 1923 for keeping a house of prostitution at the Speedway Inn in south suburban Burnham,26 the same joint where “Al Brown” (probably Al Capone) had been arrested on similar charges in 1921.27 (I wrote about that Al Brown incident for the June-July 2024 issue of Chicago magazine.)

And these cousins of Otto Annoreno were reportedly key figures in the fight for the control of Unione Siciliana, which helped to spark warfare between Capone and his rival mobs.28 Did Otto have anything to do with all of that? Or did he just happen to be on their family tree?

Robert E. Crowe. Chicago Daily Tribune, November 2, 1924, via Wikimeida.

A few months before Otto Annoreno approached Catherine and Charles Hoffman about the Green Mill Gardens property, he’d run for election as a Republican candidate for the Cook County board. He campaigned with support from the Illinois attorney general, Edward Brundage, and the Cook County state’s attorney, Robert E. Crowe.29

As a member of Crowe’s slate, Annoreno would have been seen as a law-and-order candidate. Crowe had taken office in 1920 with the backing of the notoriously corrupt mayor Bill Thompson,30 but now he was leading a slate of candidates opposed to Thompson’s GOP faction at City Hall.31

The Broad Ax, a Black newspaper, endorsed the Sicilian produce merchant running for the county board: “Mr. Annoreno is very kindly disposed to our people, having had in his employ a colored family for more than 20 years. Mr. Annoreno seems to realize what hardships we are undergoing and … wherever he sees one of our people, he is always anxious to get acquainted with them. He is one of the successful business men of Chicago and his friends are legion.32

The Lithuanian newspaper Draugas also supported Annoreno, calling him “a successful and honest person” who would “work for the welfare of the people.” The article noted: “Mr. Annoreno is a man of wide acquaintance and a great enemy of the so-called ‘reform.’” That may well be a reference to prohibition, the reform that outlawed alcohol.33

In spite of such endorsements, Annoreno lost in the GOP primary on April 11. He was one of 47 Republican candidates running for 10 seats representing Chicago on the Cook County Board of Commissioners. Annoreno finished in 11th place—just barely missing victory.34

In the months that followed, how did Annoreno get interested in the Green Mill Gardens property? That’s unknown, but the Hoffmans later alleged that Annoreno was colluding with Tom Chamales. They claimed that Annoreno and Chamales “were for many years close friends, and were business partners in various enterprises.”35 Chamales denied that this was true.36

The Hoffmans accused Chamales of concocting a scheme to take advantage of their financial woes. They said he conspired with Annoreno to cheat them out of their property.37 According to the Hoffmans, these two men “conspired and confederated together to discourage” the Hoffmans about the value of their real estate, “with the intent … to eventually get the possession and ownership … and to divest these defendants wholly or in part of the title.”38 Chamales denied these allegations.

On July 25, 1922, Catherine Hoffman signed an agreement with Annoreno and Annoreno’s lawyer, Charles Weinfeld. She authorized Annoreno and Weinfeld to manage the property and help her pay off the mortgage and other debts. She agreed not to sell the property or add any debts without their permission. And she authorized Annoreno and Weinfeld to sell the real estate if they decided it was in everyone’s “best interest” to do so.39

Perhaps the most curious thing about this arrangement was a transfer of ownership. Catherine and Charles Hoffman signed a warranty deed, turning over 50 percent of their ownership in all of the lots making up the Green Mill Gardens site to Annoreno and his wife.40

They later denied that they ever intended to give their property to Annoreno. They said they were merely giving him a deed as a form of security or collateral. They said they didn’t realize they were losing control of the property.41 They said Annoreno took advantage of their “dire necessity and ignorance.”42

Several weeks after inking that deal, Annoreno and Weinfeld came back to the Hoffmans. Together with Chamales, they proposed a new deal on September 1. Annoreno, Weinfeld, and Chamales allegedly told the Hoffmans that “the only method of salvaging and saving the property” was to cancel their lease with Chamales.

Here’s what they proposed: The Hoffmans would sign over their remaining 50 percent ownership in the property to Annoreno. After that, Annoreno would sign over 50 percent ownership to Chamales and cancel the lease. Chamales would convey a 50 percent ownership in all of Green Mill Gardens’ fixtures and furnishings to Annoreno.

The Hoffmans would get at least $7,500 a year from the profit generated by the property (instead of the $11,000 a year they’d been getting in rent from Chamales), with a possibility of getting additional money if the profits were high enough.

Annoreno and Chamales allegedly said the property would be “hopelessly lost” unless the Hoffmans entrusted them with “the entire management and control” of it. But Chamales later denied saying any of this to the Hoffmans. He insisted that he knew nothing about this proposed agreement (a copy of which the Hoffmans presented during a later lawsuit).

The Hoffmans said they refused to sign the revised deal.43 Nevertheless, they did sign another warranty deed on September 19, turning over the remaining 50 percent of their ownership in the Green Mill Garden properties to Annoreno.44 The Hoffmans later said these transactions were “only executed by reason of the threats, intimidations and misrepresentations.”45 Chamales denied that he “entered into any scheme with … Annoreno, or anyone to compel the [Hoffmans] to yield to any request.” 46

Whether or not the Hoffmans intended to give their property to Annoreno, he now had full legal possession of it—as far as these documents showed, anyway. On September 30, he signed a warranty deed of his own, conveying 50 percent ownership to Chamales.47 In exchange for becoming half-owner, Chamales said he agreed to cancel his lease.48

As a result of all of these transactions, the ownership of Green Mill Gardens fell into question. Catherine and Charles Hoffman insisted that they still owned the property—and they still had a mortgage to pay on it. But Chamales and Annoreno had documents showing that they each had 50 percent ownership.

Making things even murkier, the deed turning over 50 percent ownership to Chamales wasn’t officially filed with the Cook County until five and a half months after it was signed.49 And the July 1922 agreement between Hoffman and Annoreno wasn’t filed in the county’s property records until four and a half years later.50

A month after Tom Chamales obtained half-ownership in the Green Mill Gardens property, his nightclub suffered a defeat at the Illinois Supreme Court in Springfield. On October 21, the justices declined to reconsider their ruling that the city of Chicago had the power to shut down entertainment at 1 a.m. in Green Mill Gardens and other cabarets.51

Chicago Daily News, November 20, 1922.

On November 20, Green Mill Gardens was the victim of another sort of indignity, when robbers invaded the nightclub and blew open a safe. Five armed men wearing masks broke in during the early morning hours that Monday. They locked up Chamales’s brother James, who was working as the night caretaker, in an icebox. And then they “souped” the safe, as the Daily News put it. They got away with about $5,000 in cash—the Green Mill’s receipts from that Friday, Saturday, and Sunday—as well as $500 worth of liberty bonds, $170 worth of government thrift stamps, and a gold mesh bag valued at $500.52

This was the second safe robbery at Green Mill Gardens in six years. Was the place being targeted by certain criminal organizations? Did the robbers get some inside information about where the venue stored its valuable items? Or was it simply an attractive target?

For one reason or another, Tom Chamales decided to get out of the business of running a nightclub, though he would stay involved in overseeing the Green Mill Gardens building. Maybe it was the criminal charges and civil lawsuits against him. Maybe he wanted to focus more on the business of real estate—the following June, Tom and his brother William would be listed in the phone book with a real estate office at 4802 Broadway, apparently on the building’s second floor.53 The recent expansion of the Green Mill Gardens building created new opportunities for Chamales to lease out storefronts and office space. And he was still the owner of the Riviera Theatre across the street, collecting an annual rent of $25,000 from the Balaban & Katz movie company.

On December 13, the Daily National Hotel Reporter reported that Chamales had new plans for the Green Mill Gardens property: He was supposedly going to turn the building into an automobile showroom, while constructing a new $500,000 dance hall on the garden west of the building, working in partnership with a restaurateur named John Raklios.54

Opening an auto dealership was a trendy idea in the neighborhood, where Broadway was becoming known as the North Side’s Automobile Row.55 Chamales himself had constructed a one-story building in 1920 at 4824 North Broadway,56 which was operating now as the Riviera Motor Sales Company in the same block as the Green Mill.57

That squat structure seems to be the same one still standing at that address,58 though its large windows were covered up by a wall of cinder blocks when it became a medical clinic in the 1970s, leaving it as what is surely the block’s ugliest building.59 It’s currently occupied by Precision Audio & Video, 4824 North Broadway.

The supposed plans for transforming the Green Mill into an auto dealer never came to be—but they suggest that Chamales was looking for different ways of using the property. On the same day those plans were reported, an advertisement in the Chicago Daily News announced that Green Mill Gardens was “Now Under New Ownership.” It also said the venue was “Under Personal Management” of Abe Arends,60 who had been the floor manager of Colosimo’s restaurant on the South Side.61

Chicago Daily News, December 13, 1922.
Joe Glaser, Chicago Daily Tribune, February 26, 1928.

The new owner was Joseph G. Glaser, who’d taken over the nightclub business on December 10,62 a week before his 26th birthday.63 Glaser’s parents were Polish Jewish immigrants,64 and his father served as the president of the Chicago Medical Society’s stockyards branch.65

Glaser himself had gone to medical school but dropped out when he couldn’t stomach the sight of dissections.66 In 1916, he was accused of peddling fraudulent medical diplomas.67 A year later, he took out an ad seeking to sell his 1917 Buick D-45 touring car, which he said he was “compelled to sell, for personal reasons.”68 Within a few months,69 he’d become one of Chicago’s first used car salesmen.70

Glaser ran “Chicago’s Largest Used Car Dealer” at 1444 to 1448 South Michigan Avenue,71 which was originally constructed in 1905 as the Ford Motor Company Showroom—the first building in an area known as Chicago’s Motor Row. (The building still stands.)72

Chicago Daily Tribune, November 10, 1917.

Glaser’s name appeared frequently in classified ads, where he came across like a printed version of a used-car salesman. For example, on May 7, 1922, he’d issued this statement to anyone who was paging through the Tribune’s classified: “Ford Touring. $195 Takes It. Just took this car in trade on larger car; must sell today in order to consummate the deal; therefore this exceptionally low price; will give a written guarantee with this car; terms arranged to suit the purchaser’s pocketbook; older Ford taken in trade.”73

Now, Glaser was getting into the business of selling Chicagoans on a night out at the Green Mill, way up on the other side of town. His background in the auto business might explain why the venue tried to attract automobile enthusiasts in late January 1923, with an ad announcing: “During Auto Show Week We Have Arranged an All-Star Show with New Entertainers.”74

That winter, Green Mill Gardens featured singers Lloyd Garrett, who’d been in George White’s Scandals revue on Broadway, and Belle Oliver.75

Other entertainers at the venue included Esther Rule, the “Toe Dancing Doll”; Milton Swartz, the “Cyclonic Jazz Dancer”;76 Percy Venerable, an African American known for performing an “oddity” titled “Dopey of the Levee”77; Eddie O’Rourke, who sang “You’ve Got to See Mamma Ev’ry Night (or You Can’t See Mamma at All)”78; and Little Mildred Manley,79 who’d been known as “Canada’s Greatest Child Vocalist” eight years earlier, when she sang the patriotic tune “‘Good Luck to the Boys of the Allies.”80


Dancing music was provided by Charley Straight and His Green Mill Orchestra.81 Straight, who was 32 at the time, had recorded dozens of rolls for Chicago’s Imperial Piano Roll Company. Over the coming decade, he was a popular bandleader, known for his “soft sweet syncopation” and described as “the aristocrat of Chicago’s musical directors.” (He would die in 1940, while working as a sanitary inspector for the city of Chicago, when he emerged from a manhole in a street and was struck by a car.)82

As Glaser took over the nightclub’s management, Chamales seemed to be stepping away from running the venue he’d created eight years earlier.83 Although Glaser was described as the venue’s new “owner,” that didn’t mean he’d purchased the building. Lawyers for Chamales told the federal court that Glaser had a lease.84 The Daily News reported that Glaser had purchased the business on contract—with a provision that he’d get his money back if the court shut down the place for a year based on evidence collected before Glaser bought it.85

Around this same time, the Green Mill Gardens corporation, led by Chamales, stopped paying fees and filing annual reports with the Illinois secretary of state’s office, leading to its eventual dissolution by court decree.86

Northwestern University sociology student Harold Charles Hoffsommer, who was writing a thesis about the neighborhood around Green Mill Gardens, mentioned the nightclub’s change in ownership. “It is also well known by those in authority that the chief reason for this exchange was the fact that the former owner did not want to bear the responsibility of violating the eighteenth amendment in connection with ‘hip-liquor’ which is constantly carried into his place by the patrons,” Hoffsommer wrote, obviously referring to Chamales.

But it’s less clear what Hoffsommer was talking about when he discussed the cabaret’s new owner. “The man who now owns the gardens is notorious in Chicago’s vice circles as a dive operator,” he wrote. “It is obviously no coincidence that such a one should buy out the Green Mill Gardens and that a Chicago court should have an injunction against this person for operating houses of ill fame and prostitution. So close is the connection between this sensual type of amusement and vice questions of the most vicious kind that it is impossible to separate the two.”

As far as I can tell from searching through newspapers, Glaser did not have any track record of running brothels, though he would become notorious in the following years. Otto Annoreno didn’t seem to have any involvement in prostitution, either. Was Hoffsommer referring to Abe Arends, who had a history of managing the mob-connected Colosimo’s, in the heart of the old vice district? Or was he getting Otto Annoreno confused with his cousin at the Speedway Inn?87 It’s hard to say, but this Northwestern grad student may have simply been hearing rumors about the guys who’d taken over Green Mill Gardens.

Meanwhile, federal prosecutors faced a puzzle: Who exactly owned Green Mill Gardens, the business they were suing for purportedly selling alcohol? In a court filing, a government official added three handwritten names to the list of defendants: Otto L. Annoreno, Joseph Glaser, and Julius Braun. The government said Annoreno now held title to the property—but it also noted that Chamales “has some equitable interest in the … real estate through some private arrangement between him and … Annoreno, which does not appear of record.”88

The feds identified Julius Braun as the manager of Green Mill Gardens,89 even though newspaper advertisements had said the place was under Abe Arends’s “personal management.” When agents raided Green Mill Gardens in mid-February, they arrested someone the Daily News described as “the head waiter,” who “gave his name as Harry Brown.”90 Was this the same person identified later in court documents as Julius Braun? Was he using “Harry Brown” as an alias—or was this simply an error by the Daily News? Was Julius Braun his true name?

This was the same time period when Al Capone was using “Al Brown” as an alias. The feds were also prosecuting a waiter at Colosimo’s Cafe identified as “John Brown.”91 Of course, it’s possible that some of these people actually were named Brown (or Braun), but it’s hard not to wonder if they were concealing their true identities.

I’ve seen no evidence that the Torrio mob or Al Capone took over Green Mill Gardens (for more about that, see chapter 22), but Abe Arends’s role as a manager suggests a connection between the Green Mill and Colosimo’s, a South Side joint tied to the Torrio gang. Annoreno’s membership in the Unione Siciliana raises suspicions of another possible link. Meanwhile, Glaser was running an auto dealership in an area of the South Side where the Torrio mob was powerful. In the years after Glaser’s short stint as the Green Mill’s boss, he would become known as an associate of Al Capone’s. Was Glaser already doing business with Capone in late 1922 and early 1923, when he ran the Green Mill? That’s unknown, but the possibility can’t be entirely ruled out.

Chamales’s attorneys told a judge that he no longer owned Green Mill Gardens. They said he was actually the president of an “operating company” overseeing the place. An assistant U.S. attorney argued that the judge should shut down this place where alcohol had been sold, regardless of any recent changes in ownership and management. “Fast shifts of ownership do not alter the situation,” he said.92

As prosecutors put former Green Mill Gardens manager Henry Horn on trial in February 1923—a case that was falling apart, amid growing doubts over the reliability of agent William Yaselli’s evidence—the government also brought charges against the new owner and manager of Green Mill Gardens. (For more about Yaselli, see chapter 30.)

Federal agent George Lee said he bought a pint of whiskey from Braun and another Green Mill Gardens employee for $10 on February 14. According to Lee’s affidavit, he observed that Green Mill Gardens was “equipped with furniture and glassware … which is appropriate only for use in the handling and sale of intoxicating liquor.”93

Chicago Daily News, February 16, 1923.

Around midnight on the following night, chief prohibition field agent John E. Early raided Green Mill Gardens with a team of agents, who “seized highballs from the tables before startled man and woman diners in evening dress, confiscated a small amount of liquor found in the kitchen and took the proprietor and head waiter into custody,” the Daily News reported. “… They remained in the garden for an hour and a half.”

But Early sounded disappointed by what the agents found during their raid. “I believe the Green Mill had been ‘tipped off’ to look out for trouble,” he told the Daily News. “We found plenty of empty bottles, but there was not a great deal of liquor in sight. That taken in the kitchen was only about an ounce. There were some bottles about which seemed to have been freshly overturned and I believe intoxicants had been hastily poured from them when it became known a raid was in progress.

“When liquor was taken from in front of men and women at the table there was considerable agitation. One thirsty man, about to set his lips to the rim of a highball glass, made a particular lot of stir and refused to be calmed by reference to the adage about there being ‘Many a slip ‘twixt the cup and the lip.’ We did not search patrons for ‘hip liquor.’

“The comparative scarcity of wet goods will not affect our case, in my opinion, however. A few days ago some of our agents visited the Green Mill and bought liquor, which was saved for evidence and will be presented in court.” The feds arrested Glaser and Braun (a.k.a. Harry Brown).94

Doraldina in 1920. Wikimedia.

On the same day when the feds raided Green Mill Gardens, Variety reported some news about an upcoming attraction at the venue: The popular hula dancer Doraldina was coming. The star of the 1921 movie Passion Fruit, she was famous for performing “many strange dances of the South Sea Islands never hitherto seen,”95 although she was, in reality, a white woman from San Francisco named Dorothy Mason.96

But Doraldina did not make a big splash in Chicago. The newspapers didn’t write about her, as far as I can tell. In fact, it’s questionable whether she actually performed at the Green Mill. I’ve found only one brief notice mentioning her appearance.98

On March 1, Variety reported that the cabarets on Chicago’s North Side were trying to outdo one another by featuring lavish shows and big-name entertainers—all of the cabarets, that is, except for Green Mill Gardens, which seemed to have fallen into the doldrums. “Green Mill Gardens, recently passing to new management, long a favorite resort with the younger set, somehow or other has not gotten its stride under the new control,” Variety observed.

Meanwhile, the nearby Rainbo Gardens was drawing big crowds with Ruth Etting, Ed Beck’s revue, and Frank Westphal’s orchestra. And Rudolph Valentino—who was on strike from the movies over a contract dispute with the Famous Players Film Company99—was performing at Marigold Garden.100

Chicago Daily Tribune, March 3, 1923.
Rudolph Valentino. Wikimedia.

“Chicago women have lost all restraint in their admiration of Valentino,” Variety reported. “There is no question but what he is the biggest card that amusements of any kind have known in all the period of commercial entertainment here.101

Nothing much seemed to be happening at the Green Mill, though the venue did send a band to the nearby Arcadia Ballroom for an April 10 contest to crown the Championship Dance Orchestra of Cook County.102 Twenty-five hundred people cheered for their favorites and danced until long after midnight at the Arcadia, which was at the northwest corner of Broadway and Montrose Avenue.103 The winner was the Edgewater Beach Hotel Orchestra, led by Paul Biese, who’d previously played at Green Mill Gardens.

As Biese celebrated on the following night, two men robbed him in his car, right outside his home at 4901 North Kenmore Avenue. They took $90 in cash and two diamond rings valued at $1,250 from Biese, as well as jewelry worth $6,000 from two women who were traveling with him. One of the robbers put a gun to Biese’s head and said: “Beat it, or I’ll shoot.” The musician ran down the street and telephoned the police. The cops believed the robbers had received a tip that Biese would be carrying valuables.104

By this time, advertisements and articles about entertainment at Green Mill Gardens had ceased appearing in newspapers. At some point that spring, the venue shut down. What happened? It’s possible that the new owner, Joseph Glaser, backed out of his deal as a result of all the federal litigation over alleged prohibition violations.

But as it happened, the feds were faltering in all of their efforts to crack down on Green Mill Gardens. Following the raid in mid-February—when Glaser and Braun were arrested—the U.S. government added the new evidence to its lawsuit against Green Mill Gardens, trying to bolster the evidence gathered the previous summer by Yaselli.105 But the case was dismissed anyway.

In April, the feds tried again, filing a new lawsuit against Glaser, Braun, Annoreno, and Chamales and seeking to shut down Green Mill Gardens,106 but prosecutors dropped their lawsuit several weeks later.107 The feds made one more attempt at holding Green Mill Gardens responsible for selling alcohol, bringing criminal charges against Julius Braun in September, alleging that he’d sold one pint of “colored spirits” to a federal agent back in February. But the feds eventually dropped those charges as well.108

As a legal matter, Green Mill Gardens still had the right to stay open. But Glaser’s time as the proprietor of Green Mill Gardens had come to an end. It’s unknown precisely when it closed, but Green Mill Gardens was out of business by July, when the cabaret space reopened under a new name, the Montmartre Cafe.

Joe Glaser.

Glaser found greater fame after leaving the Green Mill. In the mid-1920s, he owned two of the South Side’s most popular black-and-tan cabarets—the Sunset Cafe, at 315 East 35th Street, and the Plantation Cafe, at 338 East 35th Street—where he presented groundbreaking jazz shows by African American musicians. He was “the cafe king,” according to the Chicago Whip, a Black newspaper.109

“Mr. Glaser was greeting people at the door and running the club—the Sunset Cafe in Chicago,” Louis Armstrong recalled. “I was just a trumpet player in Carroll Dickerson’s band. But Joe has his ear open for me, and before I knew it he gave me featured billing. I’ll never forget the thrill when I came to work one night in 1926 and saw that big bright sign, ‘Louis Armstrong, the World’s Greatest Trumpet Player.’ Mr. Glaser was the first to put my name in lights.”110

Al Capone apparently didn’t like seeing that description of Louis Armstrong on the marquee. The legendary trumpeter later wrote a letter recalling what happened: “When this ugly Gangster told Joe Glaser that he must take the name of ARMSTRONG down – off of the Marquee and it was an ‘order from Al Capone’ Mr Glaser looked this Cat straight in the face, and told him these words – I think that Louis Armstrong is the world’s greatest and this is my place and I defy anybody to take his name down from there. And that was that.”111

Even though Glaser did much to promote Black musicians, “He was also a bullying vulgarian who spewed obscenities in all directions and called his black clients ‘shines’ and schwarzes,” Terry Teachout wrote in Pops: A Life of Louis Armstrong.112

Teachout called Glaser “a lower-tier gangster who made no secret of his ties to Al Capone, whose syndicate controlled the Sunset.”113 George Avakian, Armstrong’s producer at Columbia Records, said that Glaser “was frank to say he had worked for Capone, who eventually put him in charge of the brothels and music joints on the Chicago South Side.”114 For his part, Armstrong remembered Capone as “a nice little cute fat boy—young—like some professor who had just come out of college to teach or something.”115

The Daily News reported that the “most vicious criminals in Chicago” were congregating in 1925 at Glaser’s Plantation Cafe, where he mingled with big spenders including Joseph “Yellow Kid” Weil, the king of Chicago’s con men.116 At one time, Glaser posted bond for Weil (who also reportedly frequented the Green Mill117) to get out of jail.118

Joe Glaser, center, talks with Joseph “Yellow Kid” Weil outside of court in 1924 after posting bail for Weil. Chicago Daily Tribune, December 30, 1924.

Federal authorities later alleged that Glaser shared ownership of the Plantation with Billy Skidmore, a member of the North Side gambling syndicate.119

Glaser was also a boxing promoter120 who was renowned for his power to fix fights. According to Capone biographer Laurence Bergreen, “the Capone syndicate often dictated who fought whom and what the outcome would be. Their principal connection to the fight world was Joe Glaser.”121

In 1927, Glaser faced the sort of scandal that would end most people’s public careers: He was charged with raping a 14-year-old girl. After he was convicted and sentenced to 10 years in prison, he appealed the verdict—and married the girl in Kentucky. The Illinois Supreme Court threw out his conviction, noting that the girl’s story was uncorroborated. Two years later, she divorced him, alleging that he’d taken her to California and abandoned her there.122

Joe Glaser and Louis Armstrong.

In spite of Glaser’s checkered history, Louis Armstrong hired him as his manager in 1935. “Not only was Armstrong looking for someone who could settle his mob-related problems, but he wanted above all to be relieved of responsibility for his tangled business affairs,” Teachout wrote in Pops.123 “… It is safe to assume that he … used his gangland connections to ensure that Armstrong would no longer receive backstage visits from pistol-packing thugs.”124

Glaser tightly controlled Armstrong’s business affairs for the next three decades. Armstrong seemed to want it that way, but Glaser has been criticized for exploiting Armstrong. Glaser also represented Billie Holiday, and he ran the Associated Booking Corporation, which represented many of the era’s biggest musical stars, from Duke Ellington and Benny Goodman to Barbra Streisand, B.B. King, and the Allman Brothers Band.125

After Glaser died in 1969, it became clear that he’d lost much of the control and ownership over these enterprises to people associated with the mob. “All this points to the possibility that Glaser may have ‘settled’ Armstrong’s problems with the Chicago mob by promising them a piece of the action,” Teachout wrote.126

The illustration at the top of this chapter, drawn by Sid Nix, originally appeared in the Chicagoan magazine on March 2, 1929.



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123 Teachout, Pops, 208.

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126 Teachout, Pops, 365.