Friday, January 9, 2009

Eddie and Lil - Part Two

1928 was a bull market year on Wall Street, prompting hundreds of thousands of investors to funnel their savings into the stock market. On September 3, 1929, the market hit a record high, then in the following weeks, began to waver, then fall. Nervous investors began to sell, sending prices plunging further. On “Black Thursday,” October 24, securities plummeted six billion dollars. By Tuesday the 29th, stock prices collapsed altogether.

In 1931, thirteen and a half million Americans may have been out of work, but in Washington, the government kept thousands employed, and city residents were unaware of the extent to which the rest of the country had been devastated. Eddie Killeen was oblivious. The once small-time carnival gamester had by now reached the pinnacle of his underworld career.

It was not just shrewd business sense that helped Eddie rise to power, or the unspoken code among mobsters that they never testify against a fellow gangster. One of Eddie’s sisters was married to a local attorney named John Costello, the Democratic Party National Committeeman for the District of Columbia. According to Washington Herald accounts, Costello was also a man of ambition and am exhalted sense of his own importance. With the coming of Democratic Franklin D. Roosevelt to the White House, Costello began perceiving himself as the “boss” of the city of Washington and planned to appoint new, exceedingly liberal District Commissioners and an equally liberal Superintendent of Police. Eddie was arrested countless times over the years. It was commonly believed that John Costello helped protect him from conviction.

Perhaps the most sensational instance of Eddie’s “untouchability” occurred back in January 1921. During a party at the Cabin John, Maryland, Boblinger Hotel, Killeen and a man named Barnett Tanner got into a fist fight. Tanner's date, Bessie Harris, tried to intervene and in the ensuing tangle, Eddie shot her in the heart, and she died. If the shooting was accidental, Eddie was not contrite: When police arrived at the hotel, they found Eddie and his friends singing “Auld Lang Syne.”

Eddie was arrested and tried for her murder. He told jurors he had shot Harris accidentally, that he had actually been aiming at Tanner. In spite of the damning testimony, jurors found Eddie not guilty. Among those who testified against was an eyewitness to the Boblinger shooting, Evelyn La Rue. The day after the trial ended, Evelyn La Rue was found dead of poisoning in downtown hotel. Police could never prove that Eddie killed her, but the word quickly spread on the street that Eddie was not a man to cross, and his rivals began to fear him.

He would elude the law again and again. In 1930, police raided and shut down one of his gambling dens on G Street, NW. Though he was not present at the time, prosecutors showed evidence that Eddie leased the property, and indicted him for operating a gambling business. Inflamed, Eddie went to police headquarters and threatened the arresting officers.

“I wish I had been there,” he told them. “I would have shot you down like dogs.” He was tried in the District Supreme Court, but after several hours of deliberation, nervous jurors once found Eddie not guilty.

By 1932, the “Mayor” controlled more than fifty gambling establishments, most of them small operations which “laid off” their bets with his central office—this way, he ensured he would never get caught on the premises. One house, on Conduit Road, just a mile past the D.C. line, was raided a dozen times, but police never found enough evidence to indict him. They kept a close eye on Eddie for years, waiting for him to slip up. A confident man, Eddie now boasted publicly, “They can’t touch me.”

Eddie surrounded himself with several henchmen, who worked to keep his enemies at bay and ensure that underlings did not pinch any profits.

“The Mayor was always sure to have a lieutenant with no mercy in his heart,” wrote the Herald, “and a ready trigger finger to see that the boys stayed in line.” His chief lieutenants were Bryant McMahon, Jack Cunningham, Tally Day, and Joe Nally, all of them with long criminal pasts.

As his self-assurance rose, Eddie began encroaching on the territories of other syndicates, some of them quite powerful. He had long been friendly with a prominent Washington racketeer, millionaire Sam Beard, who ran the 14th Street Richmond House, a casino that served as many as 500 bookmakers. In 1933, Beard was convicted and jailed for tax fraud. Eddie solemnly promised to look after Beard’s business interests until his friend was released. Once Beard was safely out of the way, Eddie seized control of the Richmond House and began banking its enormous profits for himself.

Feeling invincible now, Eddie took the step that would prove to be his downfall. He issued an invitation to powerful mobsters across the country to come to Washington.
“This city is going to be wide open,” the Herald newspaper later paraphrased him. “See me, and you can do what you want.”

Hindered by police crackdowns in other states, many of America’s criminal “big shots” heeded Eddie’s call. Hungry for the promise of “an undisturbed heaven” of gambling and legal immunity, they flocked to the District, which was rapidly transformed into a lawless capital of gambling, plunder and murder, all fed from the profits of racketeering. The newspapers of the day were filled with editorials decrying the new crime wave. Civic groups called for a tightening of laws, and D.C. lawmakers, in turn, shifted the blame to Congress itself, which controlled the financial purse strings.

A pressured DC government, aided by the Federal government, ordered a crackdown on crime and began to take a closer look at Eddie—and his political connections. In the first blow to Eddie’s empire, the Roosevelt administration dismissed Eddie’s brother-in-law, John Costello, from his post as Democratic National Committeeman, citing “questionable family connections.” Police cracked down on out-of-town gangsters, many of whom were arrested, convicted and sentenced to new, tougher penalties. Some ended up without any livelihood at all, save for “cutthroat competition” with each other, and—said newspapers—with Eddie, who had failed to live up to his promises.

In 1932, an armed battle for underworld primacy began, and Washington streets and alleyways were bathed in the blood of fallen gang members. Eddie lost a number of friends and “lieutenants.”

His chief “lieutenant,” Bryant McMahon, was killed in a gun battle with a rival gambler, as he tried to defend Killeen’s gambling interests at a “game meeting” in the Houston Hotel.

Another henchman, Jack Cunningham was killed in a shoot-out in a 14th Street alley.

Joe Nalley was murdered in a downtown nightclub.

Talley Day, who ran Eddie’s M Street gambling house, was killed by a man named Elmer “Bulldog” Sweeney in a fight over a card table.

To make matters worse, Eddie’s old friend Sam Beard was released from prison. Discovering Eddie’s betrayal, he declared war on Eddie. In a matter of weeks, Eddie found himself suddenly stripped of all his protective armor.

With his top aides gone, Eddie promoted one of his last remaining henchmen to serve as his chief “lieutenant.” Albert Sutton was a hardened, ex-convict who had been recently paroled from the “Big Top,” the Federal Penitentiary at Fort Leavenworth, Kansas, where he was said to have organized a thriving dope ring. Rival gangsters were elated. Sutton was the weakest of Eddie’s aides and could easily be eliminated.

“Hovering in the background like jackals,” wrote the Herald, “they were afraid to make a move as long as the ‘Big Shot’ was alive.”

Around that time, Mickey McDonald, a gambler and former underling of Eddie’s who operated a large and prosperous numbers racket in Montgomery County, was looking for ways to expand his enterprise. Emboldened by Eddie’s new vulnerability, McDonald began to muscle in on Eddie's clientele, refusing to share the profits.

In retaliation, Eddie ordered his “lieutenant,” Sutton, to take out McDonald. Sutton placed a dynamite bomb—a “pineapple”—in McDonald’s car, but it failed to go off.

Fearing that McDonald would quickly strike back, Eddie called in a “big gun” from Philadelphia, a member of the then-notorious Tri-State Gang which operated along the East Coast from Virginia to New York: Tony “the Stinger” Cugino, a man law enforcement billed as one of the most ruthless and vicious killers in the underworld.

Cugino traveled to Washington to meet with Sutton. Two weeks later, they agreed on a deal. Sutton paid Cugino an undisclosed sum of money to execute Mickey McDonald.
Just before dawn on October 23, 1934, Cugino set off to accomplish his mission. He was accompanied by a driver, Howard Bailey; fellow Philadelphia gangster Bill Cleary; Sutton; and three other Tri-State gangsters: Albert McDermott (alias John “Slim” Dunn), William Cleary, and Ernest Myers.

A short time after the hit men arrived at McDonald’s Takoma Park, Maryland, home, another car approached, driven by a young Washington Herald newspaper carrier named Alan Wilson. Wilson left his car to place the morning paper in a mailbox by the McDonald’s front door. In the still-dim light, he did not notice the men crouched behind a cluster of bushes.

The unsuspecting Wilson never had a chance. “Slim” had mistaken Wilson’s car for McDonald’s and instructed Cugino and Myers to begin firing. Alan Wilson died in a salvo of shotgun fire and pistol bullets.

McDonald's wife Viola, who had been sleeping at the time, leapt from her bed to the window in time to see the attackers flee.

Bailey, Dunn, Myers, Sutton and Cleary were later arrested. They believed that Eddie was still powerful enough to get them out of jail, and, according to the Code, they refused to admit who had ordered the hit.

Bailey later attempted to break out of Lorton Reformatory and was shot dead by guards.

Cugino was arrested in New York, but committed suicide a few weeks later after confessing his criminal history.

Bill Cleary broke down, confessing to police that he had been approached by Sutton to murder McDonald, but, according to a newspaper account, he developed “amnesia” whenever Killeen’s name was mentioned.

District police took over the investigation for its obvious links to DC gambling. Investigators were certain Eddie had ordered the botched hit, but in the absence of supporting evidence, the investigation was deadlocked. As for McDonald, he had no doubt that the bullets which killed Wilson were meant for him. Nor did he have any doubt about who had ordered his execution.


A year earlier, in 1933, Washington citizens had been shocked to learn that 88 people had been murdered in that year alone and that Washington had the highest murder rate among similarly-sized cities across the nation. The Wilson killing touched the city's nerves, waking it up to the relationship between gambling and organized crime. “Enough!” cried Washingtonians, and the city declared an all-out war on crime. U.S. Attorney Leslie C. Garnett spearheaded the effort.

Numbers was a relatively new racket in Washington, and the laws against it were ineffective. One of Garnett’s first steps to combat crime was to appeal to newspapers to stop publishing racing results. The Washington Herald, the Evening Star, the Washington Times and the Washington Post all complied, but to his disappointment, this had little effect on the flourishing bookmaking industry.

Garrett began arguing either for the legalization of gambling or the revision of lenient laws and took his case to Capitol Hill. He proposed a series of amendments before the Senate District Committee, but these did not pass in either House. He then initiated a series of spectacular police raids on gambling establishments, resulting in many indictments, which were enumerated under glaring headlines across front pages.

President Roosevelt had recently formed the Federal Bureau of Investigations, endowing it sufficient resources and authority to put down the nation's gangsters from New York to Los Angeles. “G-men” joined local authorities in keeping Eddie under constant surveillance.

Eddie’s final blow came when “lieutenant” Albert Sutton’s parole was revoked and he was sent back to Leavenworth. Word quickly spread that Eddie had lost his last defense. Now, powerful Philadelphia syndicates began to move in on his territory.

Eddie fled the city, moving his records and equipment to his Brookmont bungalow, abandoning all but a few quasi-legitimate business ventures and a small numbers racket. He stored his gaming devices in a steel vault in the basement, and then exiled himself for several months on the Florence K., anchored off Colonial Beach. Depressed and drinking heavily now, he waited for the heat blew over, and used his new free time to plan his comeback. He boasted to his few remaining friends that he was planning on setting up a gambling establishment that would rival even the upscale Mohican Lodge, one of two stone “castles” along Conduit Road, near Glen Echo, Maryland.

Sometime during this period, he re-encountered a thirty-seven year-old woman whom he had known briefly during his youth in Georgetown. Her name was Lillian Callaghan Maddox.


She was born Lillian Alice Callahan in March 1898, to Alice Wills Baker, a nurse, and Timothy Callahan, a Georgetown blacksmith. Her parents were respectable working-class Georgetown immigrants. Her father had been a wheelwright and was among the hundreds of Irish laborers who had earlier come to Washington to build the C&O canal. Their first home was a squat frame house on Prospect Avenue. They later moved into a larger home in the 3200 block of P Street, NW, just a block away from the Killeen house.

Neighbors called Lillian a "bad apple,” “ahead of her time.”

Former neighbor Jane Ward remembers Lil as pretty and clever, “from a good Catholic family, but she just got mixed up with the wrong crowd.”

Early on, Lillian developed a fascination for Eddie Killeen, and neighbors said she frequently passed by a Wisconsin Avenue saloon where Eddie worked. Here, one neighbor claimed, Eddie also ran an upstairs brothel, and he alleged that Lillian took a job there as a “hostess.”

Lillian later told police that she first met Eddie in 1911, when she was only thirteen years old. When she was fifteen, Eddie, twice her age, seduced her by promising to marry her.

By 1915, Lillian was working as a salesclerk at Hecht & Company downtown, still living in her family’s P Street, NW, home. On November 3rd of that year, at the age of only 17, she married a cigar clerk named Richard Lewis Collins. Father Edwin Corbetts performed the ceremony at Holy Trinity Church only after obtaining special dispensation from the Diocese, as Collins was not a Catholic. Collins lived with the Callahan family for several years, but no details are known about the marriage itself, which later dissolved.


Lillian first discovered opiates during her childhood. After she fell from a garden wall, at the age of six or seven, doctors prescribed narcotics for her pain. This was not an uncommon practice at the end of the 19th century, when opiates were freely dispensed for headaches, pain, and even menstrual cramps. Until they were banned early in the twentieth century, over-the-counter patent medicines--containing up to forty percent opiates by volume—were widely available, and led many down the path to addiction. By the 1880’s, there were an estimated 300,000 opiate addicts in the United States, most of them women, and a great many of them from the upper and middle classes.

For decades, physicians had freely prescribed opiates to “innocent addicts,” viewing them not as criminals, but as pathetic victims to be spared the pains of withdrawal from drugs. In 1914, the US passed its first drug law, the Harrison Narcotic Act, a tax measure regulating the import, manufacture, transport and sale of opiates. Doctors were still permitted to prescribe drugs, and narcotics clinics still operated in dozens of American cities. However, in 1919, the US Supreme Court ruled that physicians could no longer provide narcotics to addicts. Clinics across the country were shut down, and by 1924, a total prohibition was in place.

This saw the birth of the street drug trade. Having no legal access to drugs, addicts all over America were forced to turn to illegal sources to support their habits. Dealers quickly grew wealthy, and addicts were forced to commit petty crimes to pay the increasingly high price of drugs. Many women addicts were forced to turn to “houses of ill fame” as sources of opiates.

Lillian was arrested ten times between 1924 and 1933. At 26, she was arrested for the first time and fined for disorderly conduct—the legal euphemism for being under the influence of alcohol or narcotics. At the time she was working as a clerk at Washington’s Union Station. By now divorced from her husband Richard Collins, she was still using her married name.

In spite of her weakened leg, Lillian had a reputation as a fighter who could rival any man. In 1930, after a car struck hers, she pursued the motorist into his downtown office, where, said the Washington Herald, she rained blows on him sufficient enough to drive the desperate man back out into the street. It took four police officers to subdue her.

In the 1920s, Lillian married a Union Station co-worker, a gambler named John Maddox. The couple later separated, but remained friendly for years. Maddox would later subsidize, in part, her legal defense in her later trial for Eddie Killeen’s murder, and stood by her throughout her trial.

In 1932, she briefly took up with a local hoodlum called “Hoofsie” Davis.” In June, the two traveled to Atlantic City. There, she was arrested in connection with the murder of a small-time racketeer named "Milsey" Henry, killed the previous April. Police accused Hoofsie of driving the getaway car for the murderer. Lillian was charged with hiding Hoofsie from justice and briefly jailed, however, the case was dismissed for lack of witnesses.

In February 1933, she was arrested for narcotics charges and sentenced in April to serve from one to two years at Lorton Reformatory. At that time, the Washington Herald labeled her “a drug peddler and operator of an opium den.” She was released from Lorton on probation thirteen months later, in May 1934 and promised anxious friends and neighbors she would go “straight.”

It was that year that she was reintroduced to Eddie Killeen, the man to whom she had lost her virginity so many years earlier. He took Lillian for a cruise on the yacht where he was by now living in exile, and in May of 1934, the two began secretly living together, splitting their time between her Third Street, NW, apartment, the Florence K., and his Brookmont bungalow.

It did not take long for Eddie’s wife Florence to find out about the relationship.

“Oh, I don’t remember exactly when it happened,” she later told reporters. “A year or so ago, I guess. He never talked about her. But I knew. There’s always a friend who will come and tell you about those things.”

Florence said Lillian had always held a strange fascination for Eddie, even though their meetings nearly always ended in quarrels. Though Florence downplayed her reaction to Eddie’s mistress, Florence had been privately despondent at the time. Once, she went to Lillian’s apartment when the latter was away and left a note threatening, “Next time I come here, I will blow you to hell.”

When Eddie and Lillian began living together, a desolate Florence attempted to commit suicide by turning on the gas in her Chesapeake Street home. She was revived by rescue workers, and told them, “I couldn’t go on living with him anymore.”
Eddie kept up his relationship with his mistress, and Florence eventually decided she had had enough. In September 1935, Florence filed for divorce.
“I charged desertion because I didn’t want to drag the other woman into it,” Florence later explained. “I was a better sport than she was.”

Marshals looking to serve Eddie his divorce papers found him in Lillian’s apartment. Eddie pleaded with them not to tell “the other side” where he was. Eddie opposed the divorce, and over the coming weeks and months, telephoned Florence several times, begging her to reconsider. Florence refused to back down, and after the divorce was made final, Eddie provided Florence with a generous settlement, giving her the fashionable Chesapeake Street house, paying all household bills, buying her a car, and giving her $25 a week in spending money—which was not a large sum of money by any means. One decent hat at Woodward $ Lothrop’s would have consumed an entire monthly allowance.


To be Continued...

© Cecily Hilleary, 2009

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