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The Odessa Files: The life and times of the queen of Washington's underworld

By Courtland Milloy
Washington Post Staff Writer
Friday, May 7, 2010; 1:36 PM

This story originally appeared in The Washington Post on Sept. 28, 1980.

The doorbell rang. Odessa Madre, 73, creaked slowly to the foyer and parked her walking stick at the door.

A real estate man.

"Yes, ma'am, Miss Madre, I'm prepared to make you an offer," he said. He was young and well-dressed. He carried a calculator and a Polaroid camera. He wanted the house. "Seventy-five thousand dollars -- cash," he offered for her spacious five-bedroom home in Northwest Washington.

"Please, come in. Have somep'n t' eat," the frail grandmotherly woman said kindly. Odessa Madre had just been released from prison and she was too tired to haggle much about money. Besides, she had left her teeth upstairs.

In the kitchen she mashed a panload of Jiffy muffins into two bowls of "stew." She served one bowl to the real estate man. Then, to his obvious discomfort, she slid the other bowl across the floor to Hero, her dog.

"Now," she said with a mischievous, toothless grin, "did you say $150,000 -- or did you think I was born yesterday?"

It was vintage Madre -- the disarming charming setup and biting quick wit that had made her one of the most prosperous and flamboyant hustlers who ever operated in the shadows of the nation's Capitol.

"You don' pull on Superman's cape. You don' spit into the wind," Madre recited deftly. "You don' tug the mask off the Lone Ranger and, baby, you don' mess with Odessa, okay?" With that, the real estate man was gone.

"I may be old, and I may be ugly, but I ain't dumb," she said. "That's why I was the 'Queen.'"

Having spent much of her life in and out of Washington's courtrooms and prisons for the last 48 years, Odessa Madre was finally back home -- and singing. That was the one thing that the 1952 Senate Special Committee to Investigate Organized Crime in Interstate Commerce -- headed by Sen. Estes Kefauver -- was unable to get her to do.

She had started at age 17, first swearing off men and calling herself a "black widow," then spinning a web of jill joints, bawdy houses and numbers banks that eventually passed for "organized crime," albeit in a down-home sort of way. She became the self-described queen of Washington's underworld.

Many police in Washington today who know the lowdown on the low-life in this town recall her. Perhaps no other person has seen so much of the District's narcotics, numbers and "tenderloin" trade and is still alive to tell about it.

According to one police affidavit filed in U.S. District Court here in 1975, "She practices a resourceful and shrewd form of circumspection that has enabled her to survive and thrive in her illegal activities over the past 40 years."

After monitoring her activities with two court-ordered wiretaps, one police source was quoted in court records as saying that Madre frequently gave parties at her home and that "as a matter of course, Miss Madre set out a number of bowls of cocaine, heroin and marijuana for her guests' pleasure."

But she protested that decription in a recent interview: "Everybody knows I can't stand them reefers."

Her arrest record dates back to 1932. She has been picked up 30 times on 57 charges since then, including a narcotics violation for which she spent seven years at the Federal Reformantory for Women in Alderson, W.Va.

When she was released from Alderson in 1968, she bought a $10,800 Lincoln Continental with "MADRE) license plates. Then, in 1977, she was again sentenced to prison for operating a $3,000-a-day numbers racket.

Released only a few months ago, she went out and bought a $21,000 Cadillac Seville -- Pierre Cardin edition.

Odessa Marie Madre. The land where John Hechinger built his store in Northwest Washington had been named Madre Park after her grandfather -- a Civil War veteran. Only two local families had been so honored. Now she is the last of the Madres. Born in 1907, she was the only child of a seamstress, who kept her spiffily dressed, and a barber, who let her raid his till.

Her father's shop was located on 7th Street NW, next door to Uncle Madre's pool hall. She would inherit property and prosper as this strip blossomed to cultural significance during the 1940s and 1950s.

Madre attended Dunbar High School and was graduated with honors in 1925. In those days, prominent black families around the country -- the "E-lites," as Madre called them -- tried to send their children away to Dunbar as though it were a college. Indeed, with more Ph.D.s on its faculty than any other U.S. high school, it was something of that. From Madre, a spectacular career, perhaps as a teacher, was expected.

"You wonder what made me choose the life I did? I wonder, too, sometimes," she said. "I just figure that I didn't want to be like them -- them yella gals.'" The bitterness is gone, but the vivid memory reveals a deep wound.

"They called me 'the big, black mutha with the television eyes.'" She took a slow drag off a Salem, filled her mouth with smoke. "There was only three blacks at Dunbar back then -- I mean black like me," she said. "I had good diction, I knew the gestures, but they always made fun of me.

"Like on days when we are having drill competition and we were supposed to wear the school colors -- red and black.The 'yella gals' would say, 'Oh, big, black Dessa -- you don't have to wear the school colors, just stick out your big fat red tongue.' I would try to kick 'em where they said it from, but I could never get my foot no higher than their butts."

Madre didn't have the privileged "background" that most Dunbar students had, but she did have an aunt -- a schoolteacher -- who had been graduated from the old M Street High School, the forerunner to Dunbar. The aunt had arranged for Odessa to attend Dunbar and for her to move into the fashionable LeDroit Park area with the aunt and her husband, a preacher. He helped tutor Madre in oratory and mathematics.

Located just south of the prestigious Howard University, LeDroit Park was populated by black academics living in neatly kept rowhouses and elegantly steepled mansions. There were sweeping, circular driveways and gently rolling, evergreen knolls.

LeDroit was in stark contrast to the neighborhood on upper Georgia Avenue where Madre was born. She loved her old neighborhood. Her house at 807 Barry Pl. NW was a respectable rowhouse amid tinroof shanties unevenly spaced by alleys and footpaths.

On weekends, the air there was laced with the smell of cooking collard greens and of lye bubbling in pitch-black kettles. Boys shot marbles on grassless backyards. Her grandmother, with her head wrapped in rags, rocked on the front porch, corncob pipe locked in her jaws. Jill joints did a brisk business selling bootleg. Dice and dancing feet clicked through the night.

Across from Madre's home was a stairway leading up a steep incline to the back of the sturdy, wood and brick houses that fronted on Georgia Avenue. Irishmen lived there, and because they allowed their cows to roam the alleys of the shantytown below, the area came to be known as Cowtown.

When Odessa was finished studying and reciting her lessons at her aunt's home in LeDroit, she would ask permission to go outside and play. She was forbidden by the preacher from returning to Cowtown, but a walk turned to a skip and a skip to a run and before long she was back home.

In the close-knit neighborhood blacks and Irish played checkers for hours on end, exchanging laundry and midwives, and talking cows. Virtually all the Irishmen in Cowtown were city policemen -- riding horses, walking and bicycling the beats of the District.

Odessa played with their children, friends like Tom Sweeney, Mac Mahoney, Pat O'Shea and James Barrett. And they would do battle together with the Italian and German children who lived on the other side of Georgia Avenue.

"Negroes and Irishmen got along real well," Madre recalled. "They would fight amongst themselves, but we wouldn't fight each other. If somebody outside Cowtown came to fight the Irish, the Negroes would chunk bricks at them. We were like a big happy family."

Thus began a long and prosperous relationship with members of the Metropolitan Police Department. When Madre's childhood friends grew up, they became captains, lieutenants and even superintendents in the police department, like their fathers. As the year passed and Madre became the notorious "Queen," many of her childhood buddies couldn't forget that she had once been their compatriot in the "Great Rock Chunkin' Wars" against the Italian and German kids.

When Madre was graduated from Dunbar in 1925, her parents gave her a Whippet, a sleek automobile no longer manufactured. With money inherited from the sale of Madre Park, she bought two houses in Cowtown. One she kept as a home, the other she made into a jill joint -- selling that bootleg. She was 17.

"I had made up my mind not to go to Howard. I wasn't gonna fool with those gals up there," Madre said. "And I just couldn't keep no whatchamacallit -- a man? I guess I was just born to give orders, not take 'em. What kind of man wants a woman like that?"

She had set out to build her own world in which, as she put it, there would be "nothin but the best for Dess."

"Growing up in Cowtown, you couldn't help but see what was going on," she said. "I was always a bit tomboyish and curious, so I hung around the jill joints and the gaming houses and I wanted to get in on some of the fun, too. Shoot. Why should just the boys have all the fun?"

Her expertise at mathematics came in handy. She started out buying two five-gallon tins of whiskey a day and sold the liquor at 25 cents a jill (or shot). Within a matter of weeks, she was up to four five-gallon tins a day. Her only problem was Fatty Arbuckle, her supplier, who had a competing jill joint in the neighborhood. But she would soon take care of him.

Speeding along Georgia Avenue one afternoon in her Whippet, she recalled running a stop sign and being stopped by a policeman. "The man looked at me funny, and I noticed that it was li'l Tom Sweeney, in a uniform. I said, "Tom, baby, I'm in a big hurry, How 'bout if I stop twice on the way back?" He looked at me and said, "Dess, oh, Dess, is that you? Well go 'head on.'"

In time the word was out that she was "in" with the cops. So when Madre finally ventured into Southern Maryland to confer with the owner of the still who was supplying bootleg to Arbuckle, there was little question as to why switch and do business with her. Her middleman -- Fatty Arbuckle -- was finished.

"All the big shots were looking to do business with me," Odessa said proudly. "My protection would automatically be theirs, too. I said to myself, 'Let the good times roll.'"

By 1946, court records show, Madre was operating at least six bawdy houses scattered about Northeast and Northwest Washington. She recalled employing about 20 women at one time. She opened two jill joints in Shaw, and rented a room at 16th and U streets for a large bookmaking operation.

Her headquarters were located at 2204 14th St. NW, the Club Madre. The club offered liquor by the shot, numbers by the book and girls by the hour. The late comedienne Jackie "Moms" Mabley performed there free, spending her days in Washington as Odessa's guest. The two became like sisters.

On those special nights, say when Mabley and Count Basie would appear on the same bill and Joe Louis and Nat King Cole would be in the audience, Odessa would make her grand entrance into her club -- mink from ear to ankle. That was a lot of mink, because she weighed about 260 pounds back then. Reserved, in the center of the club, was a table vacant except for a dozen, long-stemmed roses. Odessa would lead an entourage -- a trail of about six or seven beautiful "yella gals," mostly all for sale, followed by a train of lusty, well-heeled "E-lite" gents.

Her shopping sprees were so extravagant they made newspaper headlines. One account, in the Washington Afro-American, reported that Madre had entered a stor where blacks were not supposed to go. The salesgirl summoned the manager, then promptly fainted when Madre began pulling roll upon roll of hundred dollar bills from her purse, demanding to see the finest fur coat in the store.

The manager gladly brought two minks -- "the best," he told her. "This is nothing but crap," Madre said, as she strolled back to her chauffeured limousine.

At her peak, Madre's net income was estimated at more than $100,000. But she never really left Cowtown, remaining within the protection of the policemen she had grown up with, and their sons.

"I never had any big trouble," she remembered. "Some guys would have their jill joints raided or muggers would break in and rob them, but people knew better than to mess with me."

Whenever she left her house, she usually traveled with a couple of bodyguards. They were often young men whom she had befriended on the street. "I would see somebody on the street that I liked and I'd give them a little something. They would usually be right friendly with me for a while."

She was also friendly with the destitute of the Shaw neighborhood. Small kids playing on the street near her house often would be rewarded with cash for "being good children." When the "boosters" -- shoplifters -- stopped by her house to sell their booty, she would sometimes put in a special order for children's clothes. When the boosters returned, she had the clothes wrapped and sent out as gifts.

"That way I made everybody happy -- the people who worked for me and the neighbors. Some of the kids' mothers would be outdone, but nobody ever sent a present back," she said.

"Odessa was basically forced into a life of crime," said Metropolitan Police Det. Robert Lee, who worked as an undercover vice squad officer during the 1960s. "There weren't hardly any jobs for black people like her when she was coming along . . . and once you got an arrest record, you could hang it up.

"Odessa was a motherly type. She did a lot of people favors, loaned a lot of needy people money, as well as provided contracts for gambling and drugs. She knew practically every big-time gangster nationwide. She was what they called a counselor in the mob. She mediated disputes between blacks and whites, a referee. She kept a lot of people for getting hurt."

More than half of the 13 years that Madre spent in prison or jail were served after she had turned 50. Usually she was sent to dormitory-style cottages where the living wasn't so bad, but there were some hard times behind bars, especailly when she had run out of money (she ordinarily took about $500 inside with her for cigarettes and "favors").

"Because I was so old, they busually made me a counselor," she said. "I had good diction; and because I used to work the phone banks at the numbers houses, I knew how to speak clearly on the telephone."

During World War II, horse racing -- on which the daily numbers games were based -- slowed down, partly because horses were in short supply (they were being eaten). So from her small upstairs office at 16th and U streets NW, Madre and Billy "Whitetop" Simpkins started a numbers bank, which became known as "The Night Number," complete with telephones and charts and a revolving cage with a special die. The die was special because it had a "O" as well as the other six digits. Simpkins was a top numbers racketeer in Washington's black community at the time.

When trouble brewed between the two strong-willed characters (Madre recalled feeling that Simpkins was preparing to double-cross her and go into business with yet another numbers racketeer known as Puddin 'head Jones) she decided to take action.

Late one night, Madre traveled to Chicago where a friend of hers made a duplicate "Night Number" die, a rigged one. After a switch had been made for the original die, Madre told a few close friends what number to bet on that night. That was the beginning of the end of Simpkins and Jones.

Mandre's empire began to roll. She was throwing money about town for lavish clothes, trips and cars. She kept some money in the bank, but most was stashed in her house for wedding and divorce celebrations, bail bonds, gambling and for "ice," the term used for police protection.

"You know, I practically ran that damn police department," she said. I don't know how many thousands of dollars I gave [Pat] O'Shea [a former superintendent of police] to stay out on the streets."

She began to rent more houses in other parts of the city. Sometimes she rented out rooms, occasionally complete with girls. "I didn't set out to get into the 'trick' trade," Madre said. "But I had come to know so many white fellows, and you know how they are, they love some colored gals. So I'd pay a girl $25 and tell her to be at such and such a place at a certain time and, hell, we'd both make out like fat rats."

By 1950, grand juries and greenhorn police officers had begun seriously investigating Madre's operations. In 1952 the Kefauver committee called her to testify. And the very nature of life in the District began to change with a supreme court increasingly concerned about equal rights for blacks.

With theaters and restaurants in "white" downtown opened to blacks, many of the well-to-do vacated the redlight district, diminishing patronage for operators like Madre.

Kefauver did his damage, too. With his traveling crimebusters committee, he stopped in more than a dozen cities, leaving smaller investigative commissions in his wake. Their target in Washington: organized crime. What they found was a pattern of payoffs by local mobsters to the police department, all funneled primarily through one person, or so it appeared based on the fragmented testimony. That person was Odessa Marie Madre.

Two sergeants testified they had been demoted and assigned to school-crossing duty because they had refused a payoff from Madre and had participated in the arrest of know gampblers -- including her. The superior officer who demoted them was John Murphy, they testified.

"Yeah, I knew him," Mandre said. "Grew up with him in Cowtown."

There was also testimony from other policemen that Madre had paid police superintendent James Barrett $2,000 a month in "ice" payments for nearly a year.

"Somebody had to give 'em the money," Madre recalled. "If anybondy was lucky enough to be able to get protection, it was because they was lucky enough to have my recommendation to the police. That's how it worked. I would tell the police if you were okay, and if it was going to be worth their while. Then you give me the money -- and I would make the drop. They wouldn't take it from anybody."

After the Kefauver testimony, Madre was constantly pursued by law enforcement officials. In 1961, at age 53, she was arrested with a one-ounce bag of cocaine valued at $1,500 and sentenced to seven years in prison.

When decective Robert Lee began stalking Madre that year, she was living in a three-story townhouse at 4426 9th st. NW. He said she had plush carpeting on each floor, with pool tables, jukeboxes, craps tables and roulette wheels in the basement. The bedrooms and baths upstairs were lavishly furnished. "She was really something else," Lee said.

The heat stayed on after her release in 1968. In 1973, agents of the Drug Abuse Law enforcement task force went to her home in Washington to serve a grand jury subpoena. In an effort to convince them that she was to ill to appear, she opened a dresser drawer to show them her medicine. They discovered a small handgun, and she was arrested again.

And again, in 1975, she was taken into custody when District police staged a raid on a 9th Street numbers bank. She was convicted and sentenced to three to seven years, but stayed out until 1977 on an appeal. That year, the U.S. Court of Appeals reduced her sentence to one to three years.

The lawyers' fees had been costly, and after returning home earlier this year, Madre found her home, which she had left in the care of a housesitter while in prison, in a shambles. "I was absolutely floored," she recalled. "My home was a mess. She let three dogs run loose in here for days." But that, Madre claims, was not the worst of it. Police say they are now investigating her charges that the housesitter wrote $15,000 worth of checks on Madre's account, leaving her with only $10,000.

"I was feeling so bad, so down, that I took $5,000 and put it down on a car," she said of the Pierre Cardin Cadillac. "That's the only thing I had worth something."

With the help of friends, she took a job with the United Planning Organization as a counselor but was unable to keep up the pace. She quit, not knowing that she was only three months short of the time needed to qualify for Social Security payments.

Once a heft 200-plus pounds, her weight had dropped to 130 by the time she was released from prison. In the few months she has been home, her weight has dropped to 110.

"Into each life, a little rain must fall," she said. "I'm thankful for having made it this far. The good times are gone but not forgotten. I really don't have no regrets.

"You say was it worth it? Child, you wonder does crime pay? I'll tell you, yes.It pays a helluva lot of money. And money is something. I don't care who you are, when you got money you can get a lot of doors open because there's always some larcenous heart who's gonna listen to you.

"And when you show 'em that money . . ." -- her sagging face grew taut and her eyes shone bright -- "if you got a wad, honey, they'll suck up to ya like you was a Tootsie Roll."

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