The Legend of Teddy Roe

The Legend of Teddy Roe #Southside #Chicago #TeddyRoe #PolicyKings #OrganizedCrime #TheStroll #Scarface #AlCapone #TheOutfit #Mafia #LaCosaNostra #UrbanLegend 

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     Looking at the history of organized crime we see two basic types of crime syndicates, enterprise and power syndicates.  The enterprise syndicates function as companies or firms, there focus is making money and do so by providing products and services.  They differ from normal companies however, because those products are either illegal or being sold and delivered in illicit, unregulated or otherwise unlawful means.   Smuggling, gambling, narcotics and prostitution are classic rackets controlled by enterprise syndicates.  While power syndicates often have enterprise syndicates they differ in that they use muscle or the threat of violence to impose taxes on the populace, limit access to the market and use violent intimidation to have their way.  Chicago, throughout the 1930s to 1950s was a hot bed for organized crime within which we saw both types of syndicates emerge.  While films such as Scarface have made Al Capone and his Outfit power syndicate legends of Organized Crime Lore, the infamy of Teddy Roe and his efforts to ward off the Outfit's incursions into the black belt and take over the enterprise syndicates of the Stroll and their lucrative policy wheels earned him the knick name of "Robin Hood" by his contemporaries.   

       In the first half of the 20th century, Chicago was a booming and progressive town and the Southside of Chicago rivaled Harlem as the center of the African American cultural renaissance.  The clubs, the cabarets, the jazz music, the black and tan bars and policy wheels all drew crowds along the Stroll in Southside Chicago.  In order to be elected in Chicago, you had to carry the black belt, an in order to carry the black belt you had to cut deals with Southside's power brokers to deliver votes in exchange for protection and so the black policy kings rose to prominence.  Among the most well renowned of the Policy Kings were the Jones Brothers.  Born, "poor as church mice. Now they have millions."  While their income primarily came from the gambling venues they operated, the brothers invested their profits wisely in legitimate businesses (Chepesieuk).  During a depression era when blacks were "the last hired and the first fired" they offered employment and stability, keeping money gambled away on the policy wheels within the Southside community by providing capital for locally owned banks to lend to local business  that were able to create jobs (Haller).    They invested in property, variety stores, grocery stores, hotels, beauty parlors and haberdasheries.  The Jones brothers spent lavishly, however, usually on themselves and were not the most generous in terms of social-welfare agencies and schools as many of the other local policy kings did.  Still, the fortunes the Jones brothers accumulated were impressive, they were taking millions of dollars off the street and their nephew, celebrated music composer and producer Quincy Jones, once bragged to us at the American Society of Composers Authors and Producers that in 1030 his uncles the Jones Brothers "took 30 million off the streets of Chicago;" an impressive accomplishment in the depression era.  With the politicians and police on their payrolls the Jones brothers enjoyed immunity to continue growing their fortunes. 

    Across Chicago, Al Capone and the outfit was also making their rise.  "With the start of Prohibition in 1920, the manufacture and sale of bootleg beer constituted the most lucrative source of revenue for the Outfit."  The Outfit also controlled the jukebox racket and had significant investments in the music industry.  Its said, "Capone took control of the gang in the mid-1920s, and during the next six years, he embarked on a spree of murder and violence to consolidate his control over organized crime in the Chicago area."  Capone and the Outfit's brutal ruthlessness and violent suppression of competition separate them from the enterprise syndicates of the black belt.  Capone and the Outfit would be better identified as a power syndicates.  "Capone was behind what mob historians agree is the most famous incident in U.S. organized crime lore: the St. Valentine’s Day Massacre on February 14, 1929. Scarface wanted to rub out Bugs Moran, who had tried to kill his good friend, Johnny Torrio. Capone went to winter at the lavish Miami estate he had recently bought, leaving the hit on Moran in the capable hands of “Machine Gun” McGurn. McGurn, in turn, hired out-of-town hit men to do the job. Dressed as cops, the hit men lured Moran gang members to a garage. Moran’s men mistakenly thought the police were raiding the garage. They did not have a chance and were gunned down in a hail of bullets. Ironically, Moran did not show up at the garage and survived the assassination plot. (Chespesiuk)"  Capone was immortalized by Howard Hughes famous film, "Scarface."  Make no celebrations about it, however, Capone and his men were ruthless murders without regard for anything other than their profits.  Throughout the 20s and thirties, Capone and the Outfit kept their distance from the Stroll and its lucrative policy wheels, leaving ample opportunity for African American entrepreneurs living in Chicago's South side.  

     During the 1920s, Teddy Roe was still living in Arkansas, working as a bootlegger.  He soon married and moved to Detroit to work in the Auto Industry.  When he lost his job, he moved out to Chicago and began working for Ed Jones in a tailor shop.  His real job was to do the bookkeeping for a policy wheel they operated and pulling numbers at another wheel a few blocks away.

    The old cliche, more money, more problems proved true, and as the profits soared so did the scrutiny and attention of the IRS.  With investigations continuing, "Ed Jones falls on the family sword for back taxes and serves 28 months in Terre Haute where he meets Billy Skidmore, bagman for Ed Jones and Sam "Mooney" Giancana, an "ambitious, but small-time member of the Outfit, the Chicago branch of La Cosa Nostra."  

    Neither intelligent, sophisticated or diplomatic as some of the more memorable mafiosos of the era, Giancana was described in a police report as a “snarling, sarcastic, foul-tongued, sadistic psychopath.” His nickname was a modification of “mooner,” which meant a “nut case.” Carl Sifakis, a mob historian described Giancana as “the most ruthless of the top bosses of organized crime. (Chepesiuk).”  In all I can read and research there's really not a redeeming quality to Giancana aside from a thuggish determination to squeeze his way in on money.  Ed Jones would have been wise to keep his distance and his mouth sealed however while locked up at Terre Haute Ed Jones, Giancana, and Skidmore spent their time together, reminiscing on their feats and planning for their release. Jones "bragged and talked at length about his gambling empire in the Black Belt, his immense wealth, lavish lifestyle, the legitimate business interests, and the estates he owned abroad."  Giancana is said to have "just listened, soaking it all in (Chepesiuk)."  In violation of the unwritten code of the Southside, Jones even offered to bring Giancana and Skidmore into the policy racket once they were released from prison.  

    With Ed Jones locked up his former understudy Teddy Roe shined.  "In one way, Teddy Roe was a lot like Ed Jones. He, too, had a fondness for the finer things in life. He wore custom-made suits, monogrammed silk shirts, alligator shoes, painted ties, and wide-brimmed hats." By the early 1950s Roe's reign as policy king was official and he spent $50,000 decorating his flat at 5239 South Michigan.  The Chicago Defender described the apartment perfectly with one word, "Lavish."  He had a fireplace of mirrors and a six foot tv set sitting on a turntable so that it could be viewed from any corner of the room with a touch of the button (Chespesiuk.) His gangster pad had a "cooler for rare liquor and fine champagne" and was adorned with stylish rugs and wall paper to complete the ambiance.  

   As Ed Jones and Giancana were released from Prison, Giancana and the Outfit began to take an increased interest in the policy rackets.  Slowly they began moving in, flexing on the softer policy kings for a 40% cut off the top.  As a power syndicate, the groups beneath them received nothing in return and still had to cover the costs of business.  "Teddy Roe was a tough guy, the type of ally the more easygoing Jones needed. Roe had a short fuse and was mouthy, but he could back his rap with his fists. And he never backed down from a fight." Roe refused to give in against the Outfit, and was determined to push back. "Giancana got frustrated when he realized that sweet talk and intimidation, the carrot and the stick, would not work on the brash policy operator. He could not manipulate Roe the same way he did Jones.  In 1945, Giancana tested Roe’s mettle by trying to shake him down, warning him that Giancana had the full weight of the Outfit behind him." But Roe just laughed in his face, promising to never bend under the pressure of any white gangster.  Tensions were heating up.  Roe and Giancana's egos clashed on numerous occasions and on one occasion nearly escalated to gun fire.  "It happened at an old storefront building on Roosevelt near Paulina in the West Side black district in a bar that Giancana owned called the Boogie Woogie.  The nightclub was a popular destination for Roe and other members of Chicago’s black criminal elite who came to hear Nat King Cole and other popular black performers."

Leaving his bar, Giancana deliberated bumped into the policy king and his entourage. “What are you doing in a black bar?” Roe asked Giancana. He answered, “I own it. And one day, I’m going to own you.” With Egos come tempers and "Roe turned into a raging bull, grabbing Giancana’s coat lapels and shouting, “Why you dirty motherfucker, I’ll fuckin’ kill you!”  Sam Giancana's brother, Chuck and Jimmy New York, the bar manager, stepped up, pulled out their guns and shoved them into Roe’s ribs. Giancana warned, ”You’re over your head,” as he swaggered out of the bar. Giancana left without further event, but had his fill of Roe’s stubborn bravado and began planning his next move. One night, he told Chuck, “I’ve had it with Roe. He is a no good son-of-a-bitch.” Chuck added, knowing the answer “And Eddie [Jones]?”  Sam concluded, “He’s seen his day, too. Shit. I kind of like the guy. I don’t want to take him out, but he won’t move over and let us in. I got to do something about him.”  Betraying the brain that taught him everything he knew about the policy racket, Giancana began planning an offensive into the Black Belt's stronghold.

    In 1946 "that something happened," with Giancana orchestrating “the first major kidnapping of a Negro in Chicago history.” On May 11, 1946, at about 11 P.M., Eddie Jones, along with Mrs. Frances Myles, his accountant, finished tallying the daily receipts at the Ben Franklin store he owned.   Jones and his wife, Lydia, and his driver, Joseph Brock, drove Mrs. Myles to her house at 4338 South Parkway. Brock pulled the car up to the curb in front of the Myles house.  As he got out with Mrs. Myles and escorted her to the door noone noticed the two cars waiting across the street. Brock returned to the car but before they could drive off two white males ran up to Jones’s side of the car and ripped open the door. With hats covering their eyes and long overcoats, white handkerchiefs disguising their mouths and noses, they waived sawed-off shotguns.  One of the men asked, "Is this Ed Jones?" to which Jones replied, "Yes, I'm Ed Jones. Why?"  They ordered him to get out and go with them, responding, "We wantcha."  Jones demanded, "Why are you doing this?" to which the gunman insisted he "Come on, get out.  We are in a hurry. We mean business."  Lydia tried to stop the men from taking her husband, but she was pushed back and the man took the butt of his shotgun to the back of Ed Jones neck.  They dragged Jones to the car and threw him in the back, as Lydia attempted to slow the kidnappers screaming "You're not going to take my husband, they're kidnapping my husband!"  The tussle captured the attention of some nearby police who pursued the kidnappers in their cruiser.   Policeman Michael Durrance and William Barber took up the chase with Jones' car following close behind.  One of Jones kidnappers shattered the rear window and delivered payloads from his sawed off shotgun, wounding Officer Durrance.  Officer Barber pulled to the side of the road to tend to his wounded partner, but radioed in his report to the precinct and out to other officers in the area.  Fleeing on Forty-sixth street the kidnappers somehow managed to get away.  Surprisingly, days passed with no word, no request for ransom, no calls or letters asking for money. 

     The papers and street were abuzz with speculation.  Did Jones fail to pay off Capone and the Outfit?  Was it an act of revenge from a broken promise?  Was it because Jones was making moves to enter the record vendor business the Outfit considered off limits for anyone outside of their cartel?  The newspaper, the Chicago Defender identified Sam Giancana as "the worst type of double crosser" with a "prison record as long as your arm."  The police brought in Giancana for questioning but frustrated released him without charges.  Ed Jones brother George, flew back from Mexico City with is mother but kept a low profile in seclusion.  Ed Jones was released after $100,000 was paid, an amount negotiated down by George from $250,000.  With Ed Jones freed, "Immediately, the Chicago police and the FBI began a nationwide manhunt for two suspects in the Jones kidnapping: Grover Duliard, a suspect in the killing of Harry “Red” Richmond, a West Side bookie and a former bodyguard of mobster Bugs Moran, and Virgil Summers, who was wanted in a series of bank robberies. Both had prison records (Chepesiuk)."  Ed Jones was relieved declaring, "Im the happiest man in the world" and while he was blindfolded with adhesive tape and had his ears plugged with cotton, he was kept "in a room with a bed and other conveniences."  Jones made it sound as if it had been a regular vacation. 

   It wasn't long before the true story became public, with Giancana planning and executing the entire kidnapping, watching from the second car outside of the Myles household.  The purpose of the attack was to break the Jones aura of invincibility and strike fear in the hearts of other Black Belt Policy Kings.  With Giancana issuing a "cooperate or die" ultimatum, Ed Jones agreed to surrender his entire policy operation to Giancana and the Outfit.  Two weeks after being freed, Ed Jones packed up his things and fled for Mexico City where their family owned several villas.  Its been rumored that they fled to Mexico City "with just enough time to grab Thirty million dollars."  The Jones enjoyed a comfortable retirement, and their departure opened up Teddy Roe's opportunity to star.  

     With the Jones leaving and agreeing stay out of the policy racket permanently in exchange for a $200,000 per year stipend from the Outfit, the remaining black policy kings feared for their fortunes, seeing Ed Jones inclusion of the Outfit in his racket as a plague.  It was rumored a kidnapping attempt was made on Teddy Roe.  Leaving the Boston Club he was followed in his Cadillac.  As he exited his car, four men chased and fired at him as he escaped through an alley.  Teddy Roe denied the attack, claiming, “I can walk down any street, day or night, without fear of being bothered by hoodlums.” Confidential reports to the crime commission suggest otherwise.  Just a week later, assassins shot and killed Robert Wilcox.  In 1946, Wilcox was a business partner with Teddy Roe at the Boston Club, the attack sent fear and hinted at the new administrative policy of Capone's men.  While the murder was never solved and competing theories about whether it was Capone's men that killed him for talking with the feds, for refusing to sell gambling equipment to the Outfit, or Black Policy kings who murdered him because he planning to sell gambling equipment to the Outfit. The "Police sergeant Carl Nelson, who headed the murder investigation, said he believed robbery was the motivation. “Wilcox was not a high-powered racketeer,” Nelson explained. “He was simply a machine operator and probably his only connection with any racket was as a repairman of the machinery used in the game. No guy would have to rub him out or try to muscle in. We are working on the stickup theory (Chepesiuk, Ron (2009-09-01). Black Gangsters of Chicago).” 

      The Outfit moved in on the policy wheels one by one, demanding a 40% "off the top of the policy," taking their percent before payments were made to "winners, workers and corrupt officials and to cover other expenses."  In close association with the Chicago policy racket, Gary, Indiana was the next city to feel the squeeze of the Outfit.  A man connected to the Outfit emptied a .38 pistol into Louis Buddy Hutchins back, leaving the policy king dead with 20,000 mourners visiting his funeral.  

      In 1950, Big Jim Martin was political power in the 28th Ward and considered an effective worker for the Democratic Alderman, George D. Kells. His position and connections could not protect him, however, and on "November 15, 1950, at Central Avenue and Washington Boulevard, shotgun pellets ripped into Martin’s shiny Cadillac."  John Philip Cerone carried out the hit for the Outfit and while Martin took a shot in the neck, he lived. The FBI caught Cerone on tape bragging,  “When I banged the guy [Jim Martin], I caught him full load . . . but it had to go through a Cadillac. I blasted him twice. Joe says, ‘Is this guy dead?’ And I said, ‘Sure, because when I nailed him, his head went like that, you know.’  But he was wrong. 

     The Outfit had taken control nearly every policy wheel in Chicago, Teddy Roe was the last hold out.  Roe held the policy wheels between Roosevelt and Halsted streets and was making more than one million annually. "Chicago’s black community loved him for his brave stand against the white mob." He became an urban hero for refusing to cut and run.  The Outfit's efforts at intimidation failed.  The Outfit's efforts to buy him out failed, and even as more and more of his men were showing up dead he held out.  Shots were fired putting his wife and children in danger, his house was even bombed but Teddy Roe stood strong.  The stereo brawler refused to go down easy.  

     In 1950 the US Senate levied an investigation into Organized Crime with high profile Godfathers of La Cosa Nostra and leading gangsters, black and white were called to testify.  Teddy Roe, Ed Jones, Jake Guzik and Tony Accardo, among others- were on the Senate Committee's list. Questioned by George S. Robinson of the Kefauver Committee, Roe spared no details in explaining his hustle. 

GEORGE ROBINSON: How do they make a bet? 

TED ROE: Well, some writers go from door to door, and the people play on their book, and they have some place they turn their book in, and then there are stations where they go to play. 

ROBINSON: Suppose I gave you twenty-five cents to make a bet. Does the writer put it in the book? 

ROE: He writes it in a book and gives you a ticket for it. 

ROBINSON: What does he do after he has circulated around his area? Where does he take the book? 

ROE: He has some place he takes it, maybe a flat somewhere, and turns it in after the drawings. 

ROBINSON: To whom does he turn it in?

ROE: He turns it in there to the cashier of the wheel that [sic] works for the wheel.

ROBINSON: Is there another method by which you can name a bet on the wheel? ROE: Well, by playing in a station.

     Roe identified nearly two dozen past and present policy kings who took the lion’s share of the multimillion-dollar-a-year gambling racket, including himself and the Jones brothers. Roe suggested that only one of his employs ever received a jail sentence for their role in the policy racket and while the game was illegal, fines were a reasonable expense easily absorbed by the profits of the policy wheels. 

     The most profitable wheel in Chicago was the "Maine-Idaho-Ohio" wheel which the Jones originally owned, but was operated in partnership with Teddy Roe bringing in an annual take of around $6 million.  Roe paid the Jones brothers a $200,000 annual stipend from the take.  "The Outfit hoped to use Jones’s testimony to implicate Roe so that Giancana could finally take over the Black Belt policy racket. In return, the Outfit would allow Ed Jones to move back to Chicago and live unmolested."  Jones and Roe were arrested on policy-racketeering conspiracy as they left the courtroom.  They were both freed on bonds.  Roe and Jones denied making bribes, but admitted to making "donations" to certain precinct captains at Christmas, and campaign contributions to both Democrats and Republicans.  

     As the excitement of the Kefauver committee passed, the Outfit got back to business and high on its agenda was getting rid of Teddy Roe.  Giancana offered Roe $250,000 in cash to quit the policy racket to which Roe replied, "I'd rather die first."  Giancana responded, "Well, my friend, you just might."  It took time, but the talk amongst the Outfit was that Roe's number was up, that "He'll be gone with the wind."   Leo "Needles Gianola added, "Send Roe back to the plantation somewhere and let him fertilize some fuckin' cotton."  Caifano continued, "Or back to hell where the nigger bastard came from to begin with."  Fat Lenny picked up a drink and mock toasted the man, "Here's to Teddy Roe, may the sorry motherfucker rest in peace."  Teddy Roe's days were numbered. 

       Late night On June 19, 1951, Caifano and three other mobsters began tailing Roe's Lincoln. They sped up on his Lincoln and slashed their headlights demanding Roe pull over.  The mobsters walked up to the car identifying themselves as state attorney police.  After Roe demanded, "Show me identification," the mobsters tried to jump Roe and drag him out of the car.  Roe pulled his gun and fired.  A bullet pierced Caifano's temple, spilling his brains as Fat Lenny's bloated corpse collapsed to the street. A bullet hit the other mobster in the shoulder as he fled to his car.  The police arrived and found Roe hiding, alone in the brush, however, its believed he was with another bodyguard, a chicago policeman.  Rick Roe, the son of Theodore Roe and a DEA agent recalled, "The Policy King was 'respected' by the people who lived in the community because he refused to give into the Outfit, he was like Robin Hood to them."  His son described him as "a crook with honor; he was not a loud-mouthed, flamboyant jerk and definitely not a murdering thug like the drug lords who took over that same neighborhood years later."

      After killing Fat Lenny, the police "booked Roe for murder and put him under extra-heavy guard in the Cook County jail following reports that he might be whacked in his cell."  Roe was under indictment at the time with Jones for conspiracy to violate the state authorities and after their appearance the day following the kidnapping attempt the charges were dropped and the urban lore of Teddy Roe, "the Robin Hood of the Southside," increased exponentially. Roe is said to have thumped his chest, declaring to the press, “They’ll have to kill me to take me.” Roe charged that Jones had helped the Outfit with the kidnapping. His suspicions stemmed from the fact that "Jones called him the day before the kidnapping" in an effort to find out where Roe would be at a specific time.  Strategically, "Roe was picking a fight with an old ally at a time when he was isolated and needed all the friends he could keep."

     The slaying of Fat Lenny sent shock waves threw the Outfit.  They could not believe a black punk from the Southside could pose such resistance and cause such problems.  Fat Lenny's funeral was described as "grotesque," vengeance against Roe a common subject of conversation. The police went to Fat Lenny's wake looking to arrest Giancana and other suspects from the failed kidnapping attempt.  

     They were unsuccessful and on August 4th, 1952, the Outfit sought to avenge Fat Lenny's death and eradicate the nuisance preventing their domination of the black belt gambling racket.  Two Outfit men parked their gray 1950 Chevy behind in a vacant lot across the street from Roe’s home, concealed by the cover of billboard. A quarter hour later, the Chevy pulled forward and stopped at a red light at Fifty-third and Michigan Avenue. An african American service-station attendant, saw the Chevy but assumed the occupants were policemen. He even asked the men, “Are you guys checking cars?”  The Outfit men replied, “No, no, everything is all right.” The service attendant left the gas station and headed home.  5 minutes to 11PM,  Roe informed his wife, Carrie that he was leaving the house.  Its not clear where he was going, but as left 5 shots were fired.  Carrie shouted, "Teddy!" from the window, but heard no answer.  

     After calling the police she ran outside to find Teddy Roe's bloody body laying sprawled out in the street. Five payloads from a 12-gauge shotgun had hit Roe in the back, face, and jaw. He didn't even have a chance to pull out his revolver.  "Roe was pronounced dead on the scene."

    The next day the newspapers sold on the claim, "The King is Dead!"

    The neighborhood rued, Roe should of escaped to Mexico City and declared you can never get to big for the mob.  Around 50,000 showed up to pay respect to Roe's casket.  The investigation remained unsolved for years, along with three hundred unsolved organized-crime homicides since Al Capone and outfits rise to prominence. While it wasn't a mystery for most who killed Teddy Roe, it was confirmed in the 1970s when the FBI finally caught Giancana on tape explaining why it took so long for him to take out Roe.  Giancana confessed, "I'll say this.  Nigger or no nigger, that bastard went out like a man.  He had balls.  It was a fuckin' shame to kill him (Chepesiuk, Ron. Black Gangsters of Chicago)." 

  Recent historians have pointed out that the overwhelming majority of the money collected from Teddy Roe's policy wheels went back into the community.  Today, the illinois state lottery which is based on the old policy game of the Chicago Southside, continues to draw massive purchases from the Black Belt.  Unfortunately a disproportionately small portion of those dollars spent by Southside residents ever make it back into Southside Chicago's schools with overwhelming majority of the earnings being circulated into outside school districts with significantly lower purchases of lottery tickets.  

  Looking at Southside Chicago and the Rise and Fall of its Policy Kings, we see the damage of power syndicates on local economic interests sometimes represented by enterprise syndicates.  Looking at how to get rid of the policy racket, former Southside Chicago police officer Blueitt answers, “It’s a social problem and not a police problem,” Blueitt explained. “Clean out our society— open up jobs for all and housing and medical facilities, and watch the crime rate drop.”  To halt organized crime, particularly the emergence of power syndicates, the government has a responsibly to step in and close the institutional holes that allow for organized crime to prosper and as Howard Hughes asks the government in the opening scene of Scarface, "What are you going to do about it?"

Bibliography

Ron Chepesiuk, "Black Gangsters of Chicago"

Mark H. Haller. "Policy Gambling, Entertainment, and the Emergence of Black Politics: Chicago from 1900 to 1940." Jounral of social History Vol. 24, No. 4 Oxford Umiversity Press

Robert Lombardo, "The Black Mafia: African American Organized Crime in Chicago, 1890-1950.  Crime Law and Social Change © 2002 Kluwer Academic Publishers 

Chicago Defender, "Chicago Policy King Indicted," August 30th, 1955.

"Scarface." © Howard Hughes, 1932.

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