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Shortly before 11 p.m. on August 4, 1952, Theodore “Teddy” Roe, numbers gambling boss of Chicago’s South Side, was about to enter his car outside his Michigan Avenue apartment when someone yelled his name. After he turned, two men fired five blasts from 12-gauge shotguns at him. Hit by double-o pellets in the head and chest, Roe died at a local hospital.

Three days later, a crowd estimated at more than 6,500 showed up for the funeral at a church on Wabash Avenue and thousands more walked past the $5,000 open casket of the wealthy man known as “Robin Hood” for his many donations, gifts and small loans to his employees that he regularly forgave.

No sooner had the burial ended than Chicago Police drew controversy by arresting his five pallbearers to furnish information to help solve the case. More interestingly at the time, 15 or so hoodlums were also arrested for questioning — a Who’s Who of the Chicago Outfit, including Anthony Accardo, Jake “Greasy Thumb” Guzik, Sam “Golf Bag” Hunt, Sam Giancana, Sam Battaglia, Leonard Gianola and Marshall Caifano. But the murder inquiries never produced any chargeable suspects.

Homicide detectives figured Roe’s rubout had to do with the Outfit’s longtime goal to take over the predominantly black South Side’s illegal policy wheel business from African-American kingpins such as Roe (who, ironically, was half-Italian). While other policy bosses, black and white, gave in to the Outfit’s intimidation and surrendered their businesses, Roe stridently resisted, even challenged the hoods to come get him. He hired some ex-cops as bodyguards and carried a loaded .38-caliber pistol with extra shells.

As equal partners in one of the 16 or 17 big numbers rackets in the South Side, Roe, Edward P. Jones and three other partners netted $4.9 million from 1945 to 1950, employing 70 people plus 300 bet writers on commission. The partners’ net profits hit a height of $1.1 million in 1946.

Jones had led their policy game (illegal by Illinois law since 1905) in the 1930s. Back during Prohibition in the 1920s, Outfit chief Al Capone made a deal with South Side racketeers, ceding control of policy gambling in exchange for not competing in the beer racket.

Jones himself broke the rules of the street by associating with the Outfit, more often than accounts that paint him as a blameless dupe of the Mob. While he and Giancana served time together in an Illinois state prison in 1939, Jones is said to have told Giancana how his policy wheel worked to lure South Siders to lay their mostly fruitless nickel, dime and quarter wagers.


Theodore Roe, numbers boss of Chicago’s South Side, successfully resisted the Chicago Outfit’s efforts to take over the street lottery until he was murdered in 1952.
In the early 1940s, Giancana and the Outfit, based on the West Side, set their sights on the South Side policy racket, the only illegal gambling scheme left in the city that they did not command. A study by Illinois officials found that the South Side ran at least 66 policy games and operators paid about $25,000 a week in protection money to police and politicians.

After his release from prison, Jones tried to negotiate an investment deal with Giancana to buy 2,000 jukeboxes from the Outfit to place in South Side locations. Meanwhile, Chicago Mayor Edward Kelly’s Democratic Party political machine, on the receiving end of millions in gambling profits from the Outfit, allowed the gang to have its way in vice, at Jones’ expense. The numbers games employed many hundreds in Chicago’s Black communities. Nevertheless, Jones lost credibility among some South Side residents for dealing with white gangsters.

In May 1946, Giancana, desiring to wrest control, had his goons kidnap Jones and hold him for a $250,000 ransom. Roe negotiated that down to $100,000 and assisted in raising the money for Jones’ release. Intimidated, and with a grand jury investigation on the city’s policy racket looming, Jones and his brother George fled to an estate they owned in Mexico.

Roe took over as boss of the Maine-Idaho-Ohio policy game and wired shares of the profits to partners Edward and George in Mexico. Roe used the South Side’s Boston Club as his roost of operations. The club also ran casino games. Roe and his partners often used their profits to invest in real estate and other legitimate businesses.

Top members of the Outfit approved Giancana’s plan to muscle in on Roe’s policy racket. Basking in the successful Jones kidnapping, Giancana made Roe their next victim.

That September 7, several gangsters stormed the Boston Club and fired shots at Roe, but he escaped unhurt and continued to run his games. The Outfit would terrorize other policy racketeers, ousting the Italian-American Benvenuti brothers — Julius, Caesar and Leo — after bombing their homes. “Big Jim” Martin, policy chief of a mostly Black part of the West Side, gave up when gangsters sprayed his car with bullets.

In Chicago in December 1950, both Roe and Edward Jones testified openly before the U.S. Senate’s Kefauver Committee. Roe answered in remarkable detail how his policy business worked. He said they made $12,000 per game, drew two games a day and that about 60 percent of Black South Side residents played regularly. Their year-by-year tax reports, entered into the Senate record, revealed their net profits of nearly $5 million from 1945 to 1950.

Seven months later, on June 18, 1951, four armed men blocked Roe’s car on a South Side street. In a gun battle with Roe and a bodyguard, Leonard “Fat Lenny” Caifano, a higher-up in the syndicate, was shot through the head and killed and another gunman wounded. Police could not figure if Roe or the bodyguard shot Caifano as the bullet went missing. Meanwhile, Roe, under arrest, claimed self-defense against a kidnapping, and a jury acquitted him of murder charges. The shooting of an Outfit torpedo made Roe a neighborhood hero.

After the end came for Roe in 1952, his death attracted widespread outrage in the South Side’s Black community. But once the Outfit grabbed his policy racket, the gang employed local people in the business, made Capone-like charitable donations and succeeded in currying favor among game players.

Within a couple of years, citywide policy games became the Outfit’s most profitable racket, with a net estimated at $150 million per year.

No one was ever charged in Roe’s murder. However, in 1958, before the U.S. Senate’s Rackets Committee, Chicago Police Lieutenant Joseph Morris testified he believed members of the “Young Bloods” faction of the Outfit were responsible for Roe’s killing. Those in the group included Giancana, Caifano (Fat Lenny’s brother), Battaglia and William “Smokes” Aloisio.

https://themobmuseum.org/blog/top-five-mobsters-youve-probably-never-heard-of/

Holland, Check out the book Policy Kings on the Black racketeersin chicago. Excellent read and the Outfit didn't take all of the numbers racket on the southside. There was still quiet operators that wasn't on the Outfit radar per say. Also Mickey Cogwell was allegedly one of the last modest numbers operator too.

Thanks !

The Jones Brothers

In 1946, the Jones brothers were at the top of the $25 million-a-year policy syndicate in Chicago. The three brothers, Edward, George, and McKissack (Mack), started out small, running a policy station from the back entrance of their "Jones Brothers Tailor Shop." Lead by brother Ed, the Jones trio turned a nickel game into a sophisticated business enterprise, which included the Jones Brothers Ben Franklin Store on 47th Street, the world's only black owned department store. The brothers made high level civic and social connections, but the glamorous and lavish lifestyle of the Jones boys couldn't be separated from the criminal activity that created it. Kidnappings, death threats, corrupt politics, violence, and jail time were also prominent in the brothers' lives.

The first hit team that was sent to kill Roe, included Leonard Caifano, Vincent Ioli and another hitman. Lenny Caifano was a capo for Giancanas personal crew but as we all know, Caifano was killed during the process in trying to eliminate Roe. Story goes that Giancana was allegedly quite mad for leaving Caifanos corpse on the scene and so the contract on Roe was taken by Teets Battaglia who in turn sent two of his hitmen Joe the Freak Amabile and Armando Fosco, and so Roe was eliminated. It is possible that same year Battaglia received the capo position as reward for the Roe job.

Funny fact the Jones brothers were the uncles of Quincy Jones who worked with Sinatra.

Never knew that. Thanks @H

The Italians had many links to the Jazz musicians in Chicago, Capone was a hugh Jazz fan, Count Basie and all the others.