Thursday, January 8, 2009

Eddie and Lil: Washington’s Gangland King And the Woman who Shot Him Down-Part One

"A blazing gun in the hands of an infuriated woman yesterday snuffed
out the life of big Eddie Killeen, who won his crown
as king of Washington's underworld by ruthlessly
crushing his rivals and ignoring the law..."
--The Evening Star
Saturday, November 24, 1935

It was the third week of November 1935, and Washingtonians were getting ready for the coming Thanksgiving holiday. For those without families, Dr. Grace Thompson was organizing a "Strangers' Dutch Treat Thanksgiving Dinner" in the Shoreham Hotel’s Garbo Room. Arnold’s F Street Beauty Salon was advertising Thanksgiving permanent waves for $2.50. The Marx Brothers “Night at the Opera” was playing at the Lowe’s Fox Theater.

Late Friday evening, November 22nd, thirty-seven year old Lillian Maddox accompanied her lover, fifty-year old Edward Vincent Killeen, to his Brookmont, Maryland, home. It was an unimposing yellow stucco bungalow on an unpaved lane just below Conduit Road—now MacArthur Boulevard. Lillian still kept an apartment in town, but she had been spending most of the past eighteen months with Eddie, either here in Brookmont, or on his yacht, the Florence K., anchored in the waters of the Potomac.

It had not been a happy year-and-a-half. Eddie, once a rich and powerful mobster, was now living in exile and in constant fear of his rivals and police. Lillian, just eighteen months out of Lorton Reformatory, had believed that this was going to be the start of a whole new life with a man she had loved since childhood.

This was a grim little house, little more than a way station now, as Eddie waited for a chance to rebuild his fallen empire. The wood floors were bare, the windows curtain-less. Its rooms were furnished with only a few sagging chairs and the odd, worn table. No pictures hung on the walls, only faded and grimy wallpaper depicting racing and hunting scenes.

Eddie and Lil spent most of evening in bed—a bare mattress covered with a soiled blanket—drinking heavily, likely listening to the radio.. The bedroom was littered with their cast-off clothes, empty glasses, and scattered papers. The window was not trimmed with curtains, only a smudged paper shade which they kept drawn day and night. Everywhere lay the heavy dust of neglect.

Late Friday night, the couple began quarrelling. Eddie had always been quick-tempered, but nowadays, he had become downright vicious. If his spiteful words and strong fist did not impress Lil, then waving his revolver would always put a quick end to their arguments.

During her early childhood in Georgetown, Lillian had fallen from a garden fence and severely injured her right leg. She had walked with a limp ever since, something Eddie taunted her about when he was feeling mean.

“You’re already crippled in one leg,” he told her now. That is when their fight reached a flash point. He pulled out his gun and threatened, “I’ll put a bullet in your other leg and fix that so you can’t walk.” Later, she would tell police he put the gun away, only after much coaxing on her part.

If they slept that night, it would have the heavy sleep of intoxication. If they had sex, it would have been less lovemaking than biological wrangling. If they ate, it would have been hastily scrambled eggs, or a tin of soup and some crackers, all washed down by bottles of Heurich beer, or shots of White Horse scotch.

By Saturday morning, the couple began fighting again before they even left the bed. Both Eddie and Lil were nearly nude, each wearing one of his undershirts, and nothing else.

This, their last argument, escalated quickly, fueled by fresh shots of whiskey and pushed by an alcohol-induced fury that neither was able or willing to control.

Some time around noon, Eddie announced he was leaving Lil. He intended to sail to Miami on his yacht, one of the few luxuries he had managed to keep hold of. Miami was a wide-open town, with plenty of opportunities for enterprising businessmen like himself.

Eddie had threatened to leave her many times. This time, Lil knew he was serious. Just the day before, she had overheard him calling his steward with instructions to load a stove onto the Florence K. and ready it for a long cruise. Frantic at the prospect of losing Eddie, Lil softened her approach and pleaded with him not go. She loved him. She needed him. What would she do without him? She was still battling the dope and could not face her Georgetown relations, whom she had let down so badly. Nor was she willing to return to her long-estranged husband, a local gambler named John Maddox.

Eddie, disgusted by her pleas, now went for her emotional jugular. He told her he could do better than some hopped-up, shopworn scrag like her, and, in fact, he had already reconciled with his ex-wife Florence, who would be traveling with him to Miami.

What happened next is unclear. Lillian would later testify that Eddie began to physically abuse her, blackening one of her eyes and bruising the weaker of her legs. He told her, “I’m going to kill you. You’re no good!”
“Eddie, you don’t want to do anything like that!” she told him.

Newspaper reports, too, offer conflicting versions of the events that followed. What is certain is that Eddie again seized his revolver. One account says Lillian scrambled out of the bed and gave it a good shove in Eddie’s direction. Caught off balance, he staggered, fumbled, and then dropped the gun, which she seized in an instant.

By other accounts, Lillian talked Eddie into putting the gun back down on the bedside table, and as Eddie turned away from her, she seized it and fired: One! The bullet hit him in the back. Stunned, he whirled back toward her, and she fired again. Two! He was struck in the abdomen. Three-four-five! The remaining bullets missed, lodging in the wall behind him. Eddie slumped, then collapsed to the floor.

Lillian froze, aware of a ringing in her ears, the echo of the gun’s blasts. Somewhere in the distance, she made out the shouts of children. She dropped the gun and waited, divided between the fear that he was really dead, and the fear that at any second, he would leap up and really give it to her. When he did not move, she took a few tentative steps toward him. He lay still, wedged between the bed and the wall. She pulled the bed out to get a better look. Blood had pooled around the wound in his abdomen. She knew, without a doubt, that he was dead. Throwing the blanket over his body, she then steeled herself with another shot of whiskey.

In a field behind the house, two neighborhood boys had been playing an after-lunch game of football. When they had heard the sound of gunshots, they ran for help. Lillian went to the telephone and asked the operator to connect her to the police.


The Montgomery County police force was housed in a relatively new building, a two-story stone structure in Bethesda. Built by Italian stonemasons a decade earlier at a cost of $30,000, it was the pride of the County. 30 men comprised a recently expanded force. Among them was Private E.R. Jones, who was sent to investigate the Brookmont call.

Brookmont, Maryland, was a small community tucked away off the Conduit Road, within a mile of the District line, carved twenty years earlier out of an old District park. Today, it is a peaceful, upper middle class community overlooking the C&O canal and Potomac River. During Prohibition years, however, its remoteness from town attracted bootleggers, gamblers and saloonkeepers, and the neighborhood was dubbed the “Bucket of Blood” for its Saturday night brawls.

Edward Killeen had been no stranger to the local police force. They had been keeping an eye on him for months now, hearing rumors that he was planning on opening a new gambling operation in the Glen Echo area.

Now, Officer Jones, accompanied by his partner, steered his patrol car down onto Maryland Avenue, and left onto a small, unpaved lane. Killeen's house was only a few hundred feet to the right. The officers spotted Lillian immediately. She was standing on the covered porch in a dressing gown, which did not hide the man’s undershirt she wore beneath. As they stepped onto the screened porch, the officers noted her disheveled hair, her bloodshot eyes and a badly bruised jaw.

"What's the trouble?" Jones asked.

“Come on upstairs and see for yourself,” she answered.

The officers followed her up the dim stairwell to the bedroom, then over the side of the bed where Eddie lay.

“I’m not sorry,” she told the shocked men. “I would do it again.”

Jones immediately telephoned Montgomery County Chief of Police William Garrett and Maryland State's Attorney James Pugh. Though the shooting had taken place in Maryland, Pugh then called in the District police, who had been seeking to link Eddie with a murder that had been baffling investigators for nearly a year.
Over the next few hours, officers from both jurisdictions conferred at the house, while a small crowd of curiosity seekers, including neighbors and the boys who had heard the gunshots, hovered outside.

Late in the day, Eddie's brother William and nephew Jack and two friends showed up at the house. Will was weeping inconsolably as he entered the house. The police later sent them away.

After they finished taking her statement, the officers waited while Lil dressed in a brown "ensemble,” silk stockings and T-strap shoes. She pancaked and rouged her cheeks in an effort to mask her bruises. Then she donned her best coat—plaid, tapered and double-breasted—and was led to an awaiting patrol car. By the time it reached the Montgomery County courthouse in Rockville, Washington Herald reporters were already waiting. A photo that appeared in the next day’s edition showed Lillian covering her face with one hand. She appeared to be weeping.
Lil confessed willingly to investigators.

“He said he was going to beat the hell out of me,” she told them. “It was his life or mine. He began beating me and he wouldn't stop. During the scuffle, the gun, which had been lying on a table, was knocked to the floor. I snatched it up and began firing--I don't know how many times.” Then, she added, "I'm glad I killed him,” repeating, “I would do it again.” After she signed a confession, she was formally charged with murdering Washington’s underworld “Mayor.” Later, as the steel door slammed her into her cell, she threw her hat and coat on the bunk and swore, "Damn it, in jail again!" That night, she was heard to murmur repeatedly, “Why did I do it?” Finally, before falling into an exhausted sleep, she cried out, “Well, it served the damn fool right!”

She slept for a few hours, and then woke up screaming at ten p.m. Guards sent for her Georgetown physician, who treated her cuts and bruises and gave her a sedative for what he called alcoholic “jitters.” He ordered that a guard spend the rest of the night in the cell, giving Mrs. Maddox a drink every two or three hours until she could “taper off.”

Back at the Brookmont house, investigators were excited. It was a seemingly cut and dry case of murder, but the murder was, for them, secondary. This was the opportunity District and Montgomery County police had waited months for: a chance to pry through Killeen’s papers.

For more than a year, they had believed he was behind the murder of a Maryland newspaper carrier, but had never produced any evidence. Now, they rifled through Eddie’s desk, boxing up papers and correspondence. They discovered boxes of ammunition, a double-barreled shotgun, a rifle and two .38-caliber revolvers. They located a secret room behind a steel door, filled with gambling paraphernalia. They hauled away boxes of paper, $3,000 worth of roulette wheels, gaming tables and "chuck-a-luck" cages.

Behind the house, they found cages full of gamecocks Eddie used to fight for high stakes during parties. In the early evening, an old woman came to feed them dried corn.

“I don't know nothing about nothing except that I come to feed the chickens every day like this,” she told investigators. “He paid me to. He was always good to me. I never heard no quarrels.”

Killeen had been wearing two large diamond rings at the time of his death. Police also found an expensive watch, a watch chain embedded with pearls, and a knife engraved with the initials “E.V.K.,” which they turned over to the State’s Attorney’s office.


Eddie’s ex-wife Florence first heard about his death over the radio. Shocked, she went immediately to the home of her sister-in-law, Mrs. John Costello, for what she told reporters was “comfort and advice.” Family members later took her to the W. W. Chambers funeral home in Southeast Washington to arrange for Eddie’s burial. Dressed in a fashionable plaid coat and a smart, brimmed hat, she told reporters waiting there that she wanted Killeen “to have the best in death as he had in life.”
That night, a Montgomery County medical examiner performed an autopsy on Eddie’s body. He found two slugs—one, which had entered through the back, just above Eddie’s hip. The other had entered his abdomen.

Eddie Killeen was buried on the following Tuesday morning, two days before the Thanksgiving holiday. Because he had been divorced, Eddie was denied the customary Roman Catholic funeral Mass. A priest from St. Paul's Catholic Church, however, agreed to chant the Latin litany of the dead in the funeral home’s chapel.
A crowd of more than 200 curiosity seekers gathered on the sidewalk outside Chambers. Women with babies in their arms stood alongside curious workmen, who had wandered over from a nearby construction job in time watch the pallbearers remove the casket from a hearse.

Inside, Eddie lay in an open copper casket that had cost more than $1,000 at a time when complete funerals could be arranged for $300. His ex-wife Florence had dressed him in a tuxedo that had still been hanging in their home. She had pinned a white carnation to his lapel and twined his boyhood rosary through his fingers.
The casket was surrounded by lavish arrays of yellow chrysanthemums and red roses. Family members, friends, regional breweries such as Tru Blue and Abner Drury, and even some of Eddie’s more powerful underworld enemies had signed the attached cards. Moments before the service began, an unidentified man rushed in with a wreath, saying, “I never liked Eddie Killeen, but I am sorry he had to die this way.”
As the priest chanted the litany, an organist played “Ave Maria.” Florence, in widow’s black, knelt beside her sister-in-law, crying throughout the service, “Oh, Eddie, Eddie, why did it have to happen like this?” She wept, too, throughout his subsequent burial at Mount Olivet Cemetery. Later, however, she posed dry-eyed for photographers and the press, answering questions about her life with Eddie, the gangland “Mayor” of Washington, DC.

Later, Eddie's sister Agnes Costello and her daughter, Eddie's niece, Margaret Costello Grady, would be buried with him.  It is not known whether Eddie ever had a headstone.  Today, his name is not even mentioned.

Edward Vincent Killeen was born in 1887 to a respectable Georgetown family of Irish-Catholic descent. His father, George Emmett, had emigrated from Ireland and married Margaret O’Reilly, an English woman from Liverpool.

By the turn of the century, Georgetown, once a thriving port and fashionable address, had lost its colonial charm. Where the waterfront once harbored graceful schooners, it was now a tangled mess of power company smokestacks, gas works and grim brick factories. The new industry had attracted hundreds of European immigrant workers. The town soon swelled, and to accommodate the newcomers, developers erected countless cheap row houses and carved antebellum mansions into tenement flats. Old Georgetown gradually disappeared, and its former aristocracy migrated to Dupont Circle or the quieter suburbs of Maryland and Virginia.

George Killeen opened a Wisconsin Avenue saloon, which did a lively business. He and his wife Margaret settled into a three-story brick house in the cobbled block of 3300 P Street, where they raised their nine children. George was an active Democrat and became a personal friend of political leader and lecturer William Jennings Bryan, contributing heavily to Bryan’s political campaigns. Like most of the Irish in Georgetown, the Killeens attended Sunday mass at Holy Trinity Church and sent their children to the parish school.

Little is known of Eddie's childhood. Holy Trinity parishioners and classmates later remembered Eddie as a “stray sheep” and a constant embarrassment to his family. His parents fought to keep him out of trouble. When Eddie was only a boy, his father instructed the District police to arrest him, should they ever find Eddie in the vicinity of Washington’s “red light district.”

When he was a teenager, Eddie left home and spent time as a circus barker in the disreputable environment of a traveling carnival. There he also operated small games of chance, learning the basics of a business that would someday make him rich.
By May 1906, Eddie was nineteen years old and had returned to Washington. That month, he was arrested for the first time, on gambling charges. Police failed to convict him, and it was generally believed that his father’s strong political ties had helped Eddie get off. In fact, he would be arrested time and time again, but never convicted of any crime.

Eddie began his rise, like so many of America’s notorious gangsters, during Prohibition. The passage of the 18th amendment in 1919 banned the manufacture, transport or sale of alcohol. Within only months of Washington’s having going dry, open-air distilleries began cropping up all over the dense forests of surrounding Maryland and Virginia, out of the government’s sight. Most of these were small operations, but there were exceptions. In 1922, Internal Revenue agents raided one of the city’s more sophisticated distilleries in the woods off Bladensburg Road. They confiscated $15,000 worth of distilling equipment and thousands of pounds of sugar and corn meal. The plant operated seven days a week, producing up to 200 gallons of 10-proof corn whiskey each day. Rumrunners were paid $50 to haul as much as three hundred gallons of moonshine into the District each night. They sold the whiskey to dispensers, for $5 a gallon. They, in turn sold it in the streets for $8 a gallon, pocketing the difference.

Eddie Killeen began as a dispenser. Because the 18th Amendment did not prohibit the buying or drinking of alcohol, he had plenty of eager customers. His concession prospered. He used the profits to begin a sideline business in gambling.
Washington had been a gambler’s paradise since before the Civil War. The best gambling houses had always been located on or nearby Pennsylvania Avenue. Some were princely, appointed with the finest furniture, carpets, and crystal, and attracting Washington’s elite: Congressmen, White House officials, and top military commanders. Thousands of dollars, it is said, could be traded in a single night at Faro tables.

Elsewhere in Washington, second-class gambling houses catered to the middle and lower classes. Cheaply furnished, they drew the bulk of their clients from the large numbers of business visitors to Washington. The proprietors of these houses employed “red herrings” to loiter in hotel lobbies and in the Capitol building. The decoys would introduce themselves to unsuspecting strangers, volunteer to show them around the city, and then lure them to the gambling houses. In the most squalid of these establishments, visitors would be forced to drink, then forced to play. The decoys were paid commissions on the victims’ winnings. The victims, embarrassed at their gullibility, rarely complained to police.

Gambling casinos often began as “parties.” Struggling young workers invited their friends to rented rooms and basements across Washington, and for a quarter “admission,” provide them with bootlegged whiskey (two dollars a jar—four, when flavored with a fruit extract and billed as peach or apple brandy). These were generally bare bones operations, outfitted with tables and crates, where card games were played, at penny stakes. As their operations expanded, their proprietors would branch into numbers, the illicit lottery in which random numbers are chosen to determine race winners. Or they would offer blackjack and dice, the proprietor taking a percentage of all winnings.

It was a risky business. If patrons’ guests became too noisy, police might raid them, arrest the occupants and players, and shut down the operations. If operators attracted clientele from the bigger gambling syndicates, the “small fry” were forced out of business, taken over, or murdered. Clever operators might be hired by the bigger syndicates. Some, like Eddie, kept their noses clean and thrived. As his profits grew, he opened a series of successful gambling houses in the District and Montgomery County.

After the 1933 repeal of Prohibition, Killeen applied for a wholesale beer distributor's license from the District's Alcoholic Beverage Control Board (ABC). Many board members opposed his membership on the basis of his well-established reputation as a gambler. However, because he had never been convicted of any crime, the ABC grudgingly granted him a license and, as a necessary formality, declared him “of good moral character.”

This infuriated many Washingtonians, and the resulting controversy received wide media attention. The Evening Star accused the Board of “throwing the liquor business into the hands of racketeers.”

In spite of the furor, Eddie retained his license and opened a business distributing Northampton Brewing Company beer to more than fifty small stores in the Metropolitan area. That concession was short-lived, however, because of the strong-armed tactics used by his employees: “Buy Northampton Beer or we’ll dump any other beer you buy in the gutter,” they told clients.

Losing the concession did not worry Eddie. The Repeal had driven the price of alcohol so low that there was no longer much profit in the alcohol business. The real money, he told his friends, was in gambling.


In 1926, Killeen met his future wife, Miss Florence Underhill, an attractive, young stenographer from New York. By now, nearing forty, Killeen, was an attractive man, with dark eyes that seemed to be borrowed from a Byzantine icon. He wore his hair parted on one side and pomaded back from his forehead. He dressed in elegantly tailored suits and patted his face generously with expensive toilet waters.
Florence was swept off of her feet.

“Eddie was a fine looking man,” she later told reporters. “He had a way with him.”
The couple was married on Halloween Day, 1926. Eddie bought Florence a platinum wedding band set with diamonds, and they honeymooned in Hot Springs, Arkansas-- a favorite resort of the era’s high rollers.

Florence later described the marriage as a happy one, even though childless.
“That was in the laps of the gods. We both wanted them, but never had any,” she later said.

She knew all about Eddie's gambling business but later claimed it was not until they were married that she became aware of the darker side of his operations. She spent many years urging him to give up “the racket,” but to no avail.

“Eddie was always his own worse [sic] enemy…it was no use to point out the danger to him. He didn’t know what fear was.”

Eddie and Florence moved into an elegant Tudor-style home on Chesapeake Street, N.W. He built a summerhouse in Brookmont and purchased a large, wood-trimmed motor yacht, which he christened the Florence K., after his wife. On weekends, the newlyweds frequently invited friends and Eddie’s business associates to sail out to Point Lookout, Maryland, or Colonial Beach, Virginia.

The two never had any trouble, claimed Florence, “until he got mixed up with this woman.” The woman was Lillian Maddox.

To be continued...

© Cecily Hilleary, 2009, May not be published or reprinted without permission.


Anonymous said...

I recently came accross your blog and have been reading along. I thought I would leave my first comment. I dont know what to say except that I have enjoyed reading. Nice blog. I will keep visiting this blog very often.


Meaghan said...

I believe that Eddie Killeen may be my great-great uncle. The names and dates fit pretty well. I was wondering where you got all your great information. Also, do you know if any pictures exist? Thanks so much!

Anonymous said...

Lillian Callahan was my Mothers Aunt. As children we used to visit her at a basement apartment on O street. Even as an old women she was very colorful. I have heard many stories about Tru Blue beer and Northhampton and Gambling joints around Peace Cross.
I believe one of my relatives in Florida provided the information.

Kathleen said...

Eddie was my grandmother's first cousin. Her name was Mary Katherine Killeen and she was the daughter of John Killeen -- George Emmett's brother. She called him "Uncle Eddie" and shared many of these colorful stories about him over the years before she died in 1993 at the age of 94. She remembered him as being very handsome and charming when she was a little girl in Georgetown; he was 12 years her senior.

Quondam Washington said...

Kathleen, I'd really like to be in touch! Facebook me? Cecily Hilleary

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