Feature Articles

July 17, 2000

The Legend of Tommy Roe

By John William Tuohy and Ed Becker

John William Tuohy is a writer who lives in Washingon, D.C.

"Fat" Leonard Caifano was a gregarious, jovial and at almost 400 pounds, an enormous man, generous and loyal to those he liked, a danger to those who crossed him.

A fifth grade drop out, Lenny was primarily a bookmaker who did a little light loansharking on the side with money put up by Sam Giancana. The two had worked a few bumbled burglaries together back in the Patch. And although it's been written that Fat Lenny "worshipped" Giancana, the truth is it was Giancana who idolized Caifano's easygoing style and street-tough macho.

Caifano, a gifted talker, persuaded Jake Guzak to convince the bosses to hire on the 42's as bodyguards for their wives and children when Roger Touhy escaped from Stateville in 1942. But that didn't last long, Touhy was recaptured in seventy days, so the boys went out looking for fresh cash wherever they could find it, and he found it on Chicago's South side.

In 1944, Caifano figured there was money to be made in the "wheel Games" run in the Black neighborhoods, but nobody was really sure how much money could be had in the racket, since the bosses, two generations apart Caifano and Giancana, had no use for Chicago's Blacks or their money. But, over the years, a few independent hoods had ventured into the business early and got rich. Guys like the Benvenuti Brothers, Caesar and Leo, who, according to their tax returns, each cleared $105,000 from the Chicago wheel game in late 1949. It was the Benvenuti's who did in Winston Howard, a Black policy king and close friend of Marva Lewis, Joe Lewis' ex-wife, after he refused to knuckle under and leave town.

But otherwise, the gambling and vice operations in the Black neighborhoods on the South side were left untouched by the mob. As a result, controlling most of the wheel games and other vice operation in the black neighborhoods were the fabulous Jones Brothers.

The Jones boys were the sons of a Baptist minister from the South who came to Chicago and died shortly afterwards, leaving a widow and three sons, Edward, George and McKissack. From a $16,000 life insurance policy, the boys' mother set her sons up in the taxi cab business, one of the few that operated on the South side.

The taxi business boomed and the eldest Jones boy, Edward, a former Club Car Porter for Twentieth Century Limited, drifted into the policy game. He started at the bottom, as a slip runner and, after he had learned the business, persuaded his mother to lend him $15,000 to start his own wheel. She did, and by the late thirties, the Jones brother's wheel was doing $10,000 to $15,000 a day. It grew because unlike other gamblers in the black neighborhoods, Jones paid off on time and in full. No excuses.

The Jones brothers funneled their cash into legitimate businesses and real estate, enough so that they became the biggest source of ready cash inside the Black belt.

They purchased the huge Ben Franklin department store on 47th Street, which employed 150 people. However, it was little more then a front for the Jones brothers' policy bank. They also bought an enormous food store at 43rd and Prairie and several large apartment buildings all over the South Side and in the late 1930s they added the Vienna, the Grove, the Garfield and the Alpha to their holdings to go along with their villa in France, where their mother Harriet lived, a summer estate in Peoria and another villa in Mexico, just outside Mexico City, the brothers' favorite vacation spot.

Then the entire family had chauffeured limos and lived in enormous mansions, Eddie designing and building his own twenty-one-room digs on South Michigan with custom-made French provincial furniture and gold bathroom fixtures. His wife Lydia was a former beauty queen in the Cotton Club Chorus line, who wore satin or mink every day.

They could afford it. Between 1933 and 1938, they had spent a remarkable $2,772,191.10 but paid taxes on about half that amount. But they didn't spend it all, the money was tucked away in savings accounts, government secured bonds, industrial bonds, commercial real estate and about $1.6 million in various stocks.

The Jones were light skinned, powerful and popular figures inside the Black belt. They were better educated and better mannered then most policy gangsters and cared little, if at all, for the residents of the Black belt except to take their money. They were notorious cheapskates and trusted no one from the Black belt to hold a position inside their operations. As a result, all of their key people were white, and in the end that cost them everything.

Enter Billy Skidmore.

William Henroth Skidmore started his long and checkered career in crime in Chicago's notorious Irish slum, the Valley, where, before he moved several blocks west, he ran a renowned saloon on West Lake and North Robey streets, in or about the 800 block, not far from the beer hall belonging to Paddy the Bear Ryan, legendary leader of the Valley gang.

At Skidmore's saloon, pickpockets and shoplifters gathered to divide their spoils and gamblers and pimps went to pay their protection money. Otherwise, the place served as a headquarters for Valley's pickpockets, sneak thieves and shoplifters of all sorts for whom Skidmore provided bail bonds. But what Skidmore did best was to act as a go-between, firming up deals between gangsters and politicians and serving as the bag man after the deal was worked out.

Otherwise, Skidmore was a hustler who made no attempts to pretend he could be trusted by anyone, about anything. He ran gambling joints inside the Levee, Chicago's early red light district, where he was an occasional partner in vice operations with Big Jim Colosimo, and later with Johnny Torrio.

Skidmore leaped to dubious fame in 1917 when he was indicted with seven others, including Chief of Police Charles Healey, for operating a graft ring between police and gamblers. They were all convicted and Healy lost his job, although Chicago, being Chicago, neither he nor Skidmore did any jail time.

When the incredible Anton Cermak took over the Cook County Board, Skidmore suddenly entered the scrap junk business and received a lucrative county contract to handle the scrap iron out of his junkyard at 2840 South Kedzie, which became Skidmore's new headquarters. Here, as Jake Guzak's bag man to city hall and the state legislature, Skidmore dispensed the mob's graft to police and politicians and collected protection from pimps and loan sharks who worked the rackets that the mob chose to avoid.

Skidmore's other office, when he needed to speak to gamblers working out in the county, was the personnel office of Herbert Burns, the Chief of Cook Counties Highway Patrol. Burns was into Skidmore for a small fortune in gambling debts.

However, most of Billy's business was done at the junkyard. It was there that newspaper reporters watched a Chicago police captain named Tom Harrison go every Saturday morning for almost a year to collect his graft. When confronted, Harrison baffled the reporters by saying that he went to the junkyard "to buy fresh eggs because one of kids has bad eyes."

Federal prosecutors had a different reason. They had the cop on tape. He owed Skidmore ten thousand in gambling debts.

In 1939, actually just a month after Green met Henrichsen there, Chief of the Cook County Police, Lester Laird, "declared war" on gambling in Cook County. Reporters from the Chicago Tribune were surprised to find the Chief visiting Skidmore at his junk yard operation the day after his declaration of war. In fact, the chief visited Skidmore from four to six times a month over a five-year period and was also a regular visitor to Skidmore's 260 acre estate in McHenry, Illinois.

When queried by reporters about his regular visits to Skidmore's place, the Chief replied that he had gone there "to personally harass Skidmore into obeying the law."

That same afternoon, reporters followed Laird to the Drake Hotel where he had dinner with Skidmore. When a news photographer snapped a picture of the two of them together, Laird leaped up from his table, tumbled down a flight of marble stairs and ran out of the hotel through the kitchen.

He resigned the next day.

Ah! Chicago!

In the early 1930s, Skidmore created a shake down market whereas he approached the policy kings like the Jones. He assured them that for the paltry sum of $250 a week, the mob would not interfere in their rackets. Then went to mob, paid them half the $250 and had them agree not to invade the Jones business though it had never occurred to them to try it anyway.

By 1938, Skidmore had hundreds of deals in place with pimps, prostitutes, rouge cops and burglars. A year later, Skidmore and his partner, Bill Johnson, ran as many as nineteen major gambling casinos in the city and their biggest customer was Edward P. Jones. "a man who never wore the same suit twice, lived in oriental splendor and had a credit rating of $1,000,000 with the Chicago banks."

The problem was that Skidmore, who had several deals in place with Tony Accardo, refused to pay Paul Ricca a penny for protection, thinking that his partnership with Accardo exempted him from the street tax.

It didn't. A federal grand jury indicted him for tax evasion and on March 9, 1941, he was found guilty and sentenced to two and half years in a federal pen, plus $5,000 in penalties. Skidmore started serving his sentence in late March of 1942.

Impressed with their own success, the IRS, armed with the books from Skidmore's casinos, moved in on the Jones brothers, using the log of Eddie Jones' casino losses as evidence to build their case, but it was a weak case at best, or least it was until Esra Leake, one of Jones' white employees whom the brothers cheated and then fired, turned state's evidence against them.

The IRS drew up tax evasion cases against everyone in the Jones operation and all of its family members. To save his brothers, their wives, and their mother, from going to jail, Eddie Jones turned himself in and took full responsibility, on the agreement that the case against his family was dropped. The government agreed and Jones was given 28 months at the federal prison in Terre Haute, Indiana, where he celled with Billy Skidmore and Sam Giancana, who was doing time on a bootlegging rap.

Skidmore persuaded Eddie Jones to teach Giancana about the numbers racket on the Black south side. Jones, a braggart with nothing but time on his hands and eager to impress the young Giancana, gave detailed lessons that included time, dates, places and figures. There were, Jones bragged, about thirty policy games going on in Chicago, and Jones had the largest one called the Maine-Idaho-Ohio, the names given to these games were meaningless like Calcutta-Green Dragon, the Erie Buffalo, the Harlem, the Bronx, the Whirlaway-Jackpot, the Beans-Ham and Gravy; they were only given names because the bettors liked to believe that one game was luckier then the next.

The wheels, Jones said, had two drawings a day, afternoon and night, bets were picked up every two hours by wheel men. The station operation got 25% of the total bets placed at his book, and the house got the rest. The win factor was 99%.

Giancana, a man gifted with the ability to see the big picture, sat and listened in awe. He understood everything. So did Billy Skidmore, who, cutting himself in for a third, helped Giancana map out a takeover of the Black policy rackets in the city and by the time Giancana was released from jail, he was a policy game expert and was armed with a foolproof plan.

Billy Skidmore never left prison. He died of a heart attack in his cell on the morning of February 18, 1944. Two years later in 1946, Momo Giancana was released from jail, and went straight to Paul Ricca with his idea to take over the Black policy games, but Ricca and Accardo were caught up in the Bioff scandal and its aftermath, and in their own efforts to tie up gambling across the city to listen to Giancana's ideas, although they did give it their approval.

Lenny Caifano was very interested in Giancana's new idea. For the past several months he had been moving in on some of the smaller wheels on the South Side's fringe. Now, armed with Giancana's astounding inside information on the wheel games, Caifano and Giancana traveled back to Indiana to approach cash rich Eddie Jones with an idea to corner the vending machine business across the city. The vending business, relatively new then, was perfect for wise guys because it was a cash business which meant they could steal most of the profits off the top before paying taxes. They envisioned a huge operation with thousands of cigarette, soda and novelty machines across the city. But it would take big money to set up and Jones had the cash.

Jones liked what he heard and he was eager to do business with the mob and sent orders from prison to his brother George to start bankrolling Giancana. In the mean time, Giancana and Fat Lenny supplemented their income with counterfeiting gas and food rationing stamps which gave them enough cash to move from the patch to fashionable Oak Park for Giancana and to a Gold Coast apartment for Caifano.

Of course neither the Caifano's nor Giancana had any real interest in sharing their business with Jones, but they led him on, and Giancana went out of his way to get closer to Jones who kept his word and provided the hoods with the money they needed to set up their vending business.

Flush with cash, Giancana and Caifano started buying pin ball machines, juke boxes and vending machines and appointed another 42 gang member, Chuckie English, to manage the operation. In turn, English brought in Joey Glimco, Willie "Potatoes" Daddano, Joe "Gags" Gagliano, Dave Yara and Lenny Patrick, to oversee distribution of the machines. Within six months, the operation employed about 500 people city wide.

While their 12,000 jukeboxes, cigarette and pin ball machines were legal, most of the products sold out of the machine, soda, candy, records and cigarettes were stolen from warehouse or delivery trucks around the city.

English took charge of the skimming, which was done on a fifty-fifty basis with the store owner who provided the space for the machine, Giancana and the others took their profit, an estimated $8,000,000 a year, and accountants fixed the book to show that the business actually lost money, thus avoiding any taxes.

Although he wrote off the payments, during the first year in business Giancana failed to make a single repayment on the loan that he and Caifano had made from Eddie Jones. Nor, for that matter, did they cut Jones in for a piece of the take. In fact, in May of 1946, the boys showed Jones how much he appreciated what he had done for him by kidnapping him off a Chicago Street and holding him for a ransom. They released him five days later at the corner of Loomis and 62nd Street, adhesive tape over his eyes, cotton stuffed in his ears. George Jones paid the $100,000 ransom to release his brother. That was enough for Jones. He retired to Mexico and entered the car business, and the mob took over the policy racket on the South Side with Paul Ricca placing the Manno brothers in charge.

Ricca and Accardo still didn't put much stock in the rumors that the Black policy racket would produce "more money then you could count" as Giancana had promised them it would. Or, at least they didn't until November of 1946, when Tom Manno drove Ricca and Accardo to a basement counting room where the results from the Black policy were counted. What they saw was money stacked to the ceiling in neat little piles that almost filled the room. Six years later, in 1952 the Manno brothers and their partner Sam Pardy were jailed for evading $2,000,000 in taxes from their policy racket, and that was only their 15% portion of the take.

Accardo ordered all stops pulled out. He wanted the Black policy business under his control, and he wanted in line by January 1947. Giancana said he could do it, but there was one problem: Teddy Roe, a cocky, mulatto who never liked nor trusted Giancana or the Caifano brothers and he had no intention of giving up his operation to them.

After Jones fled Chicago, Roe took over all of the gambling on Roosevelt Road and Halstead streets and everything in between, and while Roe operated everything from loansharking to simple handbooks, most of his money was made through wheel games, about $1,120,413.00 per year, all of it in pennies, nickels and dimes.

And Roe had no intention of handing it over to Giancana and Caifano. In one six month period in 1946, a total of twelve mob guys and an unknown number of Roe's thugs showed up dead on Chicago's streets and back alleys. Roe was outgunned by Fat Lenny Caifano and his boys who took over more and more gambling joints in the Black wards every day, setting up bookie operations anywhere they could, from neighborhood taverns and barbershops to church parking lots.

It was just too much money for the outfit not to control.

The fact was, they didn't want to kill Teddy Roe. Right after Jones left, Fat Lenny Caifano tried to work out a partnership agreement with Roe, who refused to even meet with Caifano. So Caifano bombed his house, fired shots at his wife and children and beat up his collectors, but still Roe fought back.

Roe's survival only made him a living legend in the Black community and as a result, more and more people came to place their bets with him. Giancana met with Roe and offered him $250,000 in cash to quit the policy rackets. "I'll die first," Roe answered. "Well, buddy boy," Giancana replied, "you just might."

In the early summer of 1951, Fat Lenny and Marshal Caifano rented the yacht Lady Lu, moored it at Burnham Harbor on the South side and for several days met with Momo Giancana, Fifi Buccieri and Vincent Ioli to discuss kidnapping Teddy Roe. It was decided that they would follow Roe for several days to determine his schedule. Once that was established, they would run him off the road, kidnap him, and then kill him once the ransom was paid.

On the June 19, 1951, Roe and his bodyguards, three off-duty Chicago cops, were driving home when the driver looked into his rearview mirror and spotted a set of bright headlights flashing behind him. The driver sped up but Roe ordered him to pull the car over to the side of the road. Roe and two of his guards stepped out of the car and walked up to the Chevy that carried Fat Lenny and Marshal Caifano and Vincent Ioli.

There are two versions of what happened next. One version, the likely version, was the Caifano/Ioli story that Fat Lenny had flashed his lights at Roe's car and pulled over to the side of the road in hopes of beginning another dialogue with the Black gambler.

The other version, the cop's version, was that after Roe stepped from his car surrounded by four gunmen, Fat Lenny drew a pistol from the car's seat, a dozen shots rang out and Fat Lenny took one to the center of the head. Although it was actually one of the cops who fired the fatal shot, Roe took credit for the killing and was arrested but the charges were dropped.

After Fat Lenny's murder, Sam Giancana, with the full power of the Outfit behind him, led a month long terror campaign through the Black neighborhoods of Chicago where Roe was hiding out. Dozens were shot at or blackjacked, a lot of Black hoodlums simply disappeared and others left town for ever.

Roe was holed up in his mansion on South Michigan Avenue, protected by a small army of hired goons. But it was over and he knew. On August 1, 1952, Roe was told by doctors that he had incurable cancer. After that, Roe stopped hiding. He dismissed his bodyguard, and on August 4, 1952, he dressed in a three-piece suit and hat and strolled down South Michigan Avenue. They killed him with eight shots to the head before he reached the other side of the street.

He received a hero's burial with his minister eulogizing him as a credit to his race. Even Sam Giancana admired Roe for his nerve and over the years they spoke about him often. In the early 1970s, an FBI microphone picked up Giancana discussing Roe: "I'll say this, nigger or no nigger, that bastard went out like a man. He had balls. It was a fuck'n shame to kill him."

Mr. Tuohy can be reached at

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