Teddy Roe: Chicago’s Robin Hood Who Defied the Entire Outfit & Paid With His Life 

 

 

No one was ever arrested for killing Theodore Roe. Not one name, not one warrant, not one day in court. 23 years later, the man most likely responsible for ordering that hit would be murdered, too, shot in his own kitchen the night before he was set to testify in front of the United States Senate.  That case is unsolved as well.

 Two killings, two decades apart,  zero convictions between them. This is Chicago, the South Side, the 1940s rolling into the 1950s. And this is the story of the one policy man who looked the entire outfit in the eye and said,  “No.” Before you get to the man, you need the block. Chicago’s South Side, the part folks called the Black Belt or Bronzeville, a narrow strip running along the lake more than 7 mi long and barely a mile wide at its broadest point, packed with more black wealth, more black 

ambition, and more black music than almost anywhere else in America during the first half of the 20th century. And almost none of it ever touched the bank. Segregation didn’t just  keep people out of restaurants and theaters, it kept them out of credit. No loans, no mortgages, no  access to the kind of capital white Chicago took for granted without thinking twice.

So, the community built its own bank. They just called it something else. They called it policy. Policy was a numbers game. You picked three digits, handed your quarter to a writer working the block, a runner carried it back to the wheel, and you waited for the drawing. Simple as that on the surface, except it wasn’t simple at all underneath.

Chicago had dozens of these wheels spinning at once, each one carrying its own name like it was a racehorse. The Erie Buffalo Gold Field, the B&O, the Windy City Subway Big Town. Hundreds of runners working the same blocks every morning. Thousands of regulars playing the same three numbers every single day like it was scripture handed down from somewhere higher.

By the 1930s, policy was generating real money across the South Side. Money that built department stores, funded churches, put down payments on houses no bank in Chicago would ever finance for a black family. It was illegal. It was also, in every way that actually mattered, the only economy black Chicago had that downtown didn’t control  yet.

Theodore Roe was born in August of 1898, son of a black sharecropper near Galliano, Louisiana. No schooling, no money, nothing on paper that should have led anywhere different from where his father stood. His family raised him in Little Rock, Arkansas, where a local tailor took him on and taught him to sew. A skill that, in the strangest roundabout way, would end up making him one of the most powerful men on the South Side of Chicago.

He bootlegged for a stretch during prohibition. Easy money in a country that had voted itself dry and then kept right on drinking anyway. Light-skinned enough to pass when it served him, sharp enough to know exactly when it didn’t. Married a woman named Carrie in 1923. Moved to Detroit, worked the assembly line alongside thousands of other black workers chasing the same promise of steady factory wages.

Lost the job when the work dried up. And like a few hundred thousand other black southerners in those exact years, riding the same wave historians would later call the Great Migration, he packed up and headed north to Chicago looking for whatever was left. At 31 years old, Rowe took a tailoring job under a man named Edward Jones, Big Ed to everybody who mattered.

Big Ed ran a tailor shop up front and a policy wheel out the back. >>  >> He needed a runner. Rowe needed a job. That’s the whole origin story. >>  >> No grand ambition required. A sewing gig that turned into a numbers gig that turned into an empire neither one of them could have drawn up on paper.

Under Jones and under the cover of the Kelly-Nash political machine downtown, the operation grew fast. $2,000 a day by 1930. $10,000 a day by 1938. Rowe got his cut of every dollar that moved through that wheel, and he kept climbing year over year while nobody downtown paid him any mind at all. By the 1940s, Rowe wasn’t running numbers for anybody else anymore.

 He was a policy king in his own right. Custom suits, monogrammed silk shirts, alligator shoes, a Cadillac parked out front of an apartment he’d spent $50,000 decorating, a fireplace made entirely of mirrors, a 6-ft television set on a motorized turntable so you could watch it from any chair in the room with the push of a single button.

In 1950, the man had style, I’ll give him that. Even if the electric bill alone probably scared the utility company half  to death. But, here’s the part that actually earned him the nickname. When an elderly woman got cheated out of her winnings by some cut-rate rival wheel, Row and his crew went and got her money back in person.

When a baby was born on the South Side and the family couldn’t cover the hospital bill, Row covered it, no questions.  When somebody died and the family couldn’t afford the funeral, Row paid for that, too. He’d walk the poorest blocks of the Stroll handing out $50 bills to whoever needed one that week.

He never built church and he never built a throne. He just made sure no widow on his streets buried her baby alone. Now, don’t get it twisted into something softer than it was. Row wasn’t running a charity with a Cadillac out front. People who crossed him or crossed his money learned fast that the same hands writing checks for funerals could close into fists just as easily.

 He had a short fuse and a mouth to match it and he backed both up whenever somebody pushed. That’s not a contradiction. On the Stroll in that era, it was practically the job description. Was he a criminal? Absolutely.  Nobody here is pretending otherwise, but ask the people who actually lived under him and you get a different word than criminal.

A Chicago police detective named Richard Barrett used to tell his son the neighborhood loved Row. Called him, in the detective’s own words, a crook with honor. Coming from a cop in that era about a black gambling boss, that’s not nothing. Here’s where the story turns. While Ed Jones was doing a stretch in federal prison over back taxes, he shared a cell with a small-time outfit hood named Sam Giancana and Big Ed, flush with pride, maybe a little careless with it, bragged about the money, about the mansions, about a wheel

>>  >> that was clearing thousands a day off poor black Chicago’s quarters and dimes. Giancana didn’t say much back. He just listened, soaked it in, filed it away for later. May 11th, 1946, 11:00 at night, Ed Jones is outside his accountant’s house on South Parkway finishing up the day’s receipts.

 Two white men in long coats and pulled down hats come out of nowhere, sawed-off shotguns drawn. “Is this Ed Jones?” one of them asks. >>  >> He says, “Yes.” They drag him into a waiting car. His wife is screaming in the street behind him. Police give chase, shots get fired, an officer takes a bullet, and then, nothing.

 No ransom note, no phone call, days of total silence while all of black Chicago held his breath. The Chicago Defender didn’t wait around to point fingers politely. They named Sam Giancana directly in print, called him the worst kind of double-crosser, a man with a record as long as your arm. Police brought Giancana in for questioning, couldn’t make a thing stick, let him walk.

Meanwhile, the FBI and Chicago police put out a nationwide alert for two other men they liked for the job, a small-time hood named Grover Duling, already wanted for a separate killing,  and a bank robber named Virgil Summers. Neither one ever stood trial for it. Nobody in the end ever did. Two weeks later, Jones came home, $100,000 lighter, his family having haggled the ransom down from a quarter million.

He packed what he could carry and relocated to Mexico with his surviving brother George, keeping his distance from Chicago for years afterward. A third Jones brother, McKissick,  never even made it that far. He died in an ordinary car accident at some point in this same era, which the Chicago Tribune itself found almost worth remarking on, since hardly any policy boss of that era got the luxury of dying quietly.

 And just like that, the entire Jones row operation, the wheels, the writers, the runners, a piece of the South Side worth well over a million dollars a year by the most conservative count, and tens of millions more once you factor in the whole policy racket, landed in one set of hands. >>  >> Teddy Roe’s hands. Sam Giancana figured taking Jones off the board would clear his path straight through. It didn’t.

Roe wasn’t built like Jones. Where Jones negotiated, Roe pushed back loud and in public the very first time anybody tried to collect what Giancana liked to call street tax, a cut off the top paid whether you wanted to pay it or not. The story goes Giancana and Roe crossed paths outside one of Giancana’s own West Side clubs.

Words turned ugly fast. Roe grabbed him by the coat. Two of Giancana’s men had pistols in Roe’s ribs before it went any further. Nobody pulled the trigger that night, but everybody standing in that doorway understood exactly what had just been promised for later. It didn’t take long for that promise to start collecting.

In September of 1946, Roe left the club on Wabash Avenue called the Boston Club and noticed the car tailing him. He ditched it on foot, made it home in one piece. A week later, his own  business partner, a man named Robert Willcox was shot dead. Chicago police at the time leaned toward calling it a robbery gone wrong, not a mob hit.

 Willcox wasn’t a major player, just a machine repairman who kept the wheels spinning. Maybe that’s exactly what it was. On the South Side that year, it was getting harder and harder to tell the difference between bad luck and a message. By 1950, the whole country got a window into this world, whether the outfit liked it or not. The United States convened a committee, the Kefauver Committee, to dig into organized crime coast to coast, broadcast live on television sets across the country for the first time in American history.

A piece of those hearings landed right in Chicago. Roue testified, sat in  front of a Senate panel, and explained plainly exactly how a numbers wheel works, how a quarter handed to a writer on a stoop turns into a payout days later from a cashier sitting in some South Side flat. He didn’t dodge a single question.

 By that point, what exactly was left to hide? He and Jones were arrested on conspiracy charges in the  weeks that followed their testimony, out on bond within the day. The hearings made for terrific television. They didn’t slow either side down for one single afternoon. June 19th, 1951. A car comes up fast behind Roue’s Lincoln. Headlights cut off.

 Men jump out claiming to be state’s attorney police. One of them is Leonard Caifano, Fat Lenny to everybody who knew him, a made man in the outfit and the brother of a capo. They try to drag Roue straight out of his own car. Roue carried a pistol everywhere he went, every single day. That night is the only reason he made it home at all.

He fired.  Caifano hit the pavement, dead before the ambulance even got the call. One more man caught a bullet in the shoulder  and ran for the dock. Chicago booked Rowe for murder that same night. Within  days, he was a free man. No trial, the case against him gone. Rowe walked out of that building >>  >> and by every account that survives, thumped his own chest in front of the reporters waiting outside.

“They’ll have to kill me to take me.” He told them. He wasn’t speaking in metaphor. He meant it down to the letter and everybody listening knew it. But killing a made man, even clean, even with a self-defense ruling behind it, is not something an organization like the Outfit let’s slide. Fat Lenny’s own funeral, by every account that survives, was a furious, ugly affair.

Vengeance against Rowe the only thing on anybody’s lips. Police actually showed up at the wake hoping to arrest Giancana and the others involved in the failed kidnapping right there among the floral arrangements. They left empty-handed  and somewhere in that crowd of mourners, men were already talking about what came next.

What came next wasn’t subtle in the least. Over roughly the next month, >>  >> Sam Giancana’s crew tore through every black bookmaker still standing on the South Side. Some faced violent intimidation in broad daylight. Some narrowly escaped attacks. Many simply left Chicago for good, never running a number again.

This pattern didn’t stop with Caifano’s death and it didn’t end there. Down in Gary, Indiana, a policy man named Louie Buddy Hutchins took a bullet courtesy of an outfit gun and still drew 20,000 mourners to his funeral. That’s how deep policy money ran through the lives of regular working people, criminal or not.

Back in Chicago, months before Caifano ever crossed paths with Roe, an enforcer named John Cerone had already shotgunned a war politician  named Big Jim Martin clean through the window of his own Cadillac. Martin survived, barely, and Cerone later bragged about the hit on an FBI wire like he was recapping a ballgame over beers.

Through all of it, Roe stayed put, holed up in that same South Michigan Avenue home, surrounded by armed men he trusted, while the city around him kept catching fire one bookmaker at a time. >>  >> The Outfit tried every angle on him, his men turning up dead in alleyways, shots fired close enough to put his own wife and kids at  risk, even his house getting bombed at one point.

 None of it worked. He didn’t blink, and he didn’t run. Money didn’t move Roe, so next came the lead. Far as Giancana figured it, Roe was already as good as dead. The Outfit reportedly put $250,000 in cash on the table just for him to walk away and disappear. Roe’s answer, more or less word for word, “I’d rather die first.

” Sam Giancana’s reply came back short and flat, something close to “Well, my friend, you just might.” August 1st, 1952, doctors gave Roe the news, >>  >> stomach cancer, inoperable, a death sentence with a timer already running, regardless of whatever the Outfit still had planned for him.

 It’s worth saying plainly, most of what we know about what happened next comes from his widow, told to reporters only after the fact that the diagnosis is what made him send his bodyguards home, made him stop hiding behind locked doors, and armed men. Maybe that’s exactly what happened. Maybe it’s the kind of story a grieving wife tells herself >>  >> to make a senseless death feel like it meant something.

Either way, here’s what’s certain. August 4th, 1952. Rhod dressed in a three-piece suit and a hat. The man dressed sharp even on what turned out to be the last night of his life. At 10:55, he told Carrie he was stepping out. She had no idea it would be the last full sentence he ever said to her. Outside in a vacant lot across the street, two men had been sitting in a gray 1950 Chevrolet parked behind a couple of billboards for about 15 minutes before pulling out toward the corner.

>>  >> A black gas station attendant named Joseph Turner noticed the car idling at a red light down the block and figured the men inside were police checking for speeders. He walked over and asked if that’s what they were doing. “No, no, everything is all right.” one of them told him. Turner believed it, finished his shift, and went home for the night.

The Chevy pulled forward, stopped at the corner, Rhod stepped out near his own front door, dressed sharp, not a bodyguard in sight for the first time in years. Five shotgun blasts rang out. Rhod never made it to his hand for his own gun. He fell steps from his front door, cut down in the street outside his home.

 Carrie heard it from inside the house, called his name out the window once, got nothing back, ran outside and found her husband’s body lying in the street not 5 minutes from where he’d kissed her goodbye. That same night before the body was even cold, newsboys on the corner of 53rd and Michigan were already hawking papers,  shouting the same three words over and over, “The King is dead.

” And black Chicago answered the only way it knew how, by showing up in numbers nobody could ignore. Thousands lining the sidewalks for blocks. Some accounts put the total closer to 50,000 people paying respects to a man the law would have called a criminal and the neighborhood called something a whole lot closer to family.

A minister at the service was remembered saying simply that Roe had a pure heart and was a friend to everyone. It got strange fast. Minutes after Roe was lowered into the ground at Lincoln Cemetery, police moved in and arrested four of his own pallbearers, hauled them in for questioning, booked them on disorderly conduct, and cut them loose on $25 bond.

One detective claimed the interrogation gave him a fresh angle on the murder. He never said what it was. In total,  police questioned 176 people in connection with Roe’s killing, Giancana among them, >>  >> along with Tony Accardo, Jake Guzik, and 10 other known Outfit men. Every single one walked.

The case stayed open officially for years. It never once got close to an arrest. The Outfit took over his wheels within days, didn’t even wait for the dirt to settle good. And years later, the FBI caught Sam Giancana himself on a wiretap talking about the man he’d spent half a decade trying to break. Giancana’s words, near enough to verbatim, “Black or no black, that bastard went out like a man.

” Coming from the man who almost certainly gave the order to kill him, that’s about as close to a confession and a compliment as history is ever going to hand you on the same plate. No one was ever charged for killing Teddy Roe. Not one name on a warrant, not one single day in front of a judge. That’s not an accident.

 That’s exactly how the whole machine was built to run. But, history’s got a strange sense of humor sometimes and a longer memory than most men plan around. Marshall Caifano, Fat Lenny’s own brother, the man who wanted Roe dead in the first place, ended up listed on Nevada’s brand new black book in 1960, banned for life from every casino in the state, fighting it all the way up to the Supreme Court and losing at every single step along the way.

And  Sam Giancana, the man who almost certainly gave the order on Roe, climbed all the way to the top of the Chicago Outfit, rubbed shoulders with the Kennedys, got tangled up with the CIA in a plot to kill Fidel Castro. Then, on June 19th, 1975, 24 years to the day after Caifano bled out on a Chicago street, Giancana was shot in the back of the head in his own basement kitchen frying sausage for a guest he trusted enough to let through his own door.

 He was due in front of committee members the very next morning. He never made it. The men who killed Roe thought they’d settled the score. 23 years later, the same kind of knock came calling at Giancana’s own door. Nobody ever did a single day in prison for either murder. Not Rose, not Giancana’s. The state of Illinois, for its part, didn’t shut policy down at all.

 It simply took it over, legalizing its own state lottery in 1974, and collecting under official government letterhead the same nickels and dimes Teddy Roe once died refusing to hand over to anybody else. The wheel never actually stopped spinning. It just changed owners and changed paperwork. Make of that whatever you want.

 I know exactly what I make of it. The man who said, “They’ll have to kill me to take me.” turned out to be right on both counts. They did, and they still couldn’t take the only thing that actually mattered.