Eddie and Lil -- Conclusion

If Eddie and Lillian had a honeymoon period, it was short-lived. From the start, constant quarrels, heavy drinking, and physical abuse—on both sides, plagued their relationship. It is difficult to understand Eddie’s feelings for Lillian, which may have been tied into guilt over having “ruined” her so many years before and reneged on his promise of marriage. Or, as some have suggested, Eddie could well have been Lillian’s source of narcotics, and their relationship could have been tied up in the complex relationship between distributor and addict, master and slave. Lillian was an attractive woman, though worn by years of drug and alcohol abuse. One early police mug shot in particular showed her faded beauty. With fine arched brows, well-shaped mouth, and saddened downcast eyes, she looked more like a Madonna from a Renaissance Pieta. Photos at the time of the murder show a heavier Lillian, eyes blackened and face puffy from drink.

It is perhaps easier to understand Lillian’s feelings for Eddie. She had met him as a young adolescent, when Eddie was already 24 years old. He was an attractive firebrand—likely glamorous to a girl just discovering her own sexuality. If, as she said, her first sexual encounter were with Eddie, it would have bonded her to him in a way that subsequent relationships may not have been able to. He had promised to marry her, but only as a ruse to seduce her, and the betrayal may have left her with a drive for a fair “settlement.” In her adult relationship with Eddie, he abused her, and as is often the case with abuse victims, she may have clung to the relationship out of a sense that it was all she deserved.

Their second affair came in the wake of the Depression, a time when there were few opportunities for women, outside of a traditional marriage. As an addict with a police record and two bad marriages behind her, she would have seen Eddie as someone who could offer her security and possibly, protection from the law.
During her relationship with Eddie, Lillian employed a housekeeper, Hannah Smith, who later described the relationship as toxic from the start.

Eddie sought to isolate Lillian from friends and family. He would often hold her as a prisoner, keeping visitors away from the house for days and weeks at a time. On one occasion, he locked Lillian aboard the Florence K., anchored on the Chesapeake Bay, and left her there alone for three weeks, threatening repeatedly to kill her. He once threatened to kill Lillian after she had refused to take part in a dangerous game: He had wanted to shoot a lit cigarette from between her fingers, just for the sport of it. On Christmas Eve, 1934, Lillian had asked Eddie for permission to deliver gifts to her Georgetown family. Eddie become so enraged that he tore off her clothes knocked her half-naked to the ground and kicked her repeatedly. Once, said Hannah, when Eddie was sitting downstairs, he shouted for Lillian, who was upstairs at the time. Getting no answer from her, he shot his pistol through the ceiling.

It was that same pistol that Lillian would ultimately use to end his life.

***

On Thanksgiving Day, 1935, Lillian was formally arranged for the Eddie’s murder. State’s Attorney James Pugh had already begun building his case. At first he was unconvinced by Lillian’s confession, and combed it carefully, looking for flaws. He found one puzzling contradiction: Lillian claimed that she shot Killeen in self-defense, after he had beaten her. However, the Georgetown doctor who had examined her in her cell the night of the murder said the bruises and cuts on her body had been three to seven days old—enough to support her claim that Eddie had beaten her, but not on the day of the murder.

Pugh had trouble accepting the fact a man with so many powerful enemies had been murdered by a penniless girlfriend. He became convinced she had not acted alone and that there may have been another gunmen in the house.

Four bullets had been fired. Investigators examined slugs from Eddie’s body and compared them to those found in the bedroom wall, but concluded that only one gun had been fired, and that the fifth chamber of Eddie’s .38 caliper pistol had been empty at the time of the shooting.

The Washington underworld was rife with speculation that Eddie’s rivals had paid Lillian to murder Killeen. Though there was no evidence to support the idea, Pugh was certain someone was backing Lillian. How else had she managed to retain Maryland State Senator Stedman Prescott, a prominent and high-priced lawyer?
Eddie’s gamester rivals made no secret that Lillian had done them a service by killing off they man they hated and feared. Some of them now approached her lawyer openly, asking whether there was a chance she might be released on bail, whether she needed anything in her cell or witnesses to testify on her behalf.

In the end, while he did not believe her story in its entirety, Pugh concluded she had acted alone.

Meanwhile, the fledgling Federal Bureau of Investigation was interested in learning what Lil may have known about interstate racketeering. Within only a few days of her arrest, her lawyer Prescott granted the FBI permission to interview Lil, and was present during the questioning. The FBI later refused to disclose what, if any information, Lil gave them.

States Attorney Pugh and a team of investigators now shifted the focus of their investigation to Eddie himself. They sifted carefully through the boxes of papers they had retrieved from the Brookmont house. Slowly, they pieced together a chronicle of Eddie’s criminal rise and his hold on District and Maryland rackets—of interest, but not the prize they were seeking: any bit of information that could link Eddie to the killing of paper carrier Alan Wilson. Three Washington detectives had spent more than a year working the case—at the time, a record for any one murder.

Finally, investigators found what they had long been seeking: a box of stationary belonging to Mickey McDonald’s Richmond House casino—physical evidence linking Eddie with McDonald.

In another part of town, the defense began putting together their case. Lillian’s estranged husband, John Maddox, retained the services of a second lawyer to assist Prescott Stedman, Harry Whelan, who had earlier helped Eddie secure his liquor license. Though separated from Lillian, Maddox said he was determined to see she was adequately represented during her trial.


Meanwhile, Washington crime lords were scrambling to fill the void left after Eddie's death. The papers called the resulting power scuffle a "dog fight" and wondered nervously who would emerge as the new "Mayor" of the DC underworld.

***

Lillian remained in jail for more than two weeks. A preliminary hearing was scheduled for the first week in December, but rescheduled because her attorney was tied up in a Prince George’s County trial.

The State outlined to the press their strategy for the upcoming preliminary hearing.
“So far as the county is concerned, we are satisfied that the slaying occurred in the manner described by Mrs. Maddox,” State’s Attorney Pugh told reporters.

At the on December 11th, her lawyer, Stedman Prescott, read out Lillian’s initial confession, in which she said that she knew what she was doing when she shot Killeen, and that he would have killed her had she not done so. Prescott told the court that Eddie “was haunted by fear that he was to be the next victim [of the mob], and carried a gun wherever he went.” Months before his murder, Eddie began to drink heavily and physically abuse Lillian.

The defense called its principal witness, Lillian’s former housekeeper, Hannah Smith, who testified to the abuse she had witnessed Eddie inflicting on Lillian.
Lillian’s Georgetown doctor testified that just two weeks before his death, Eddie had beaten Lillian in her face so severely that she needed medical attention. She had appeared in the doctor’s office with blood flowing from her mouth, her teeth nearly cut through her lower lip. Killeen, he said, had followed her and waited in his car outside. After Lillian left his office, the doctor watched from the window as Eddie threw Lillian roughly into his car and threatened to kill her again, crying, “What the hell are you trying to do?”

Lillian, heavily made up and looking far older than her age, did not testify at the hearing. However, at one point in the proceedings, she was asked why, if Eddie was so brutal, did always return to him. She answered simply, “Because I loved him.”

The following day, Judge Harold Smith reduced her first-degree murder charge. Based on the State’s evidence, he said he did not believe a trial jury “would convict her of anything more than manslaughter.” The court released Lillian on $5,000 bond to await a grand jury trial.

Lillian said nothing, but smiled. A few minutes later, she fainted into the arms of her lawyers and had to be revived with smelling salts. She then signed her bond and left the courthouse for her sister’s house in Georgetown.

Killeen's estate was assessed in late December. He had left behind $2,650, consisting of $900 cash, two diamond rings, a car, and $300 worth of prize gamecocks. His yacht was not to be found, and there was no mention of the watch and knife police had confiscated at the house.

Florence, disappointed at Eddie’s meager legacy, began looking into whether the Northampton Brewing Company, who had retained Eddie as an agent a few years earlier, would provide any residuals.

***

On January 21, a Montgomery County jury charged four men with the murder of newspaper carrier Alan Wilson: Eddie’s former chief lieutenant Albert Sutton, “Slim” Dunn, Bill Cleary, and Ernest Myers. Cleary made a deal with lawyer, confessing to his involvement in killing Wilson and implicating the other three. In return, he was given legal immunity. The court postponed setting a trial date until “Slim” could be retrieved from Alcatraz Federal prison. The others were serving time in Washington jails. Another Tri-State” member, Dewey Jenkins, kept in seclusion somewhere in Washington, was indicted after having made a confession implicating the suspects in the murder.

The following day, State’s Attorney Pugh moved to extradite “Slim” from the California prison and issued warrants for the other three suspects.

***

On the first of February 1936, Lillian was arrested for shoplifting at department store at 9th and D Streets, NW. Caught with two pocketbooks, a packet of rouge and a bottle of massage oil for a total value of $6, she was held, and then released, on a $300 bond. She told reporters she was "back running dope."

***

On February 25, Sutton, Dunn, and Myers were arraigned in a Rockville court, and their trial date set for March 30th. Cleary did not appear in court. Sutton, Dunn and Myers, “nattily dressed and clean-shaven,” said the Herald, showed no emotion as the charges were made before Judge Charles Woodward. Sutton and Dunn, convinced they could not get a fair trial in the District area, obtained a change of venue, and would later be tried in Cumberland, Maryland.

On April 4th, after the Rockville jury deliberated only an hour and a half, 37-year-old Ernest Myers was found guilty of first-degree murder.

***

On April 8th, 1936, the manslaughter trial against Lillian Callahan opened in the Rockville Circuit Court. It took only an hour to select the jury. Three times, the sheriff was forced go out into Rockville streets to round up new prospects, after several potential jurors said they had already formed opinions about the case.

Lillian pleaded not guilty. Apparently confident, she showed little interest in the proceedings.

In his opening statement, her lawyer, Prescott, described Eddie Killeen’s underworld history, telling jurors that “Big Eddie” had been “practically” the head of all gambling in the area. Only a few days before his death, Prescott said, Killeen had woken Lillian from her sleep, striking her in the face, and raving that he was planning to kill gambling rival Sam Beard and US Attorney Leslie Garnett, who had headed the capital’s crackdown on gambling rackets.

He chronicled Lillian’s relationship with her lover. State's witnesses--two police officers and Lillian's own written confession--all corroborated a history of brutality at the hands of Edward Killeen.

In light of that testimony, State's Attorney James Pugh announced he did not feel he could ask the jury to convict Lillian. That day, the jury acquitted Lillian of all charges. She left the courthouse on the arm of her lawyer, beaming to the surrounding throng of reporters and photographers.

***

The New Deal enthusiasm for patching up and mending a worn national infrastructure had by now hit Georgetown. A few years earlier, the Rockefeller Foundation had invested millions to restore colonial Williamsburg, Virginia, to better-than-original condition. Inspired, Georgetown citizens set about restoring their long-neglected township. They purchased crumbling houses at fire-sale prices and refurbished them. They mended fences and manicured gardens. Shopkeepers painted storefronts and hung new signs. Gradually, Georgetown began to hold its head up again, its decorum restored.

So, too, did Lillian set about repairing up her life. She returned to her sister's house in Georgetown, where she would live quietly for years, fighting for sobriety and respectability. If Lillian knew more about the day Eddie Killeen died, she kept it to herself. Whether she formally divorced John Maddox is not known, but she returned to using her maiden name, Callaghan.

Though she never made it back to the front pages, she was never, at least in Georgetown circles, able to completely live down her past as a Notorious Woman. Neighbors either avoided her entirely, or nervously pretended the whole affair had never happened.

Children found her fascinating, among them, Washington painter and architect James Hilleary.

“Every time she would open her purse to take out a cigarette, I'd look to see if she was carrying her ‘gat’,” he remembers.

In her later years, Lil became somewhat of a local legend. Neighbors quietly referring to her by the nickname, “Diamond Lil,” after the Mae West character, due in part to her appearance.

“She’d wear clothes—the only way to describe them is ‘costumes.’ Like Sunset Boulevard,” former neighbor Jane Ward says.

Once, some time after World War II, Lillian threw a lavish party, in what some guests saw as an attempt to reinstate herself into Georgetown society. James Hilleary attended the party at Lillian’s apartment, which she had decorated very elegantly. She had draped a silk-tasseled shawl over a white lacquered piano and filled the rooms with flowers.

“It was the funniest mixture of people you would ever want to meet. She had all the Holy Hill Irish there, you know, the pillars of the Church,” he says. “Poor Lillian. The party was going well until some unwanted guest, somebody from her past, showed up drunk and made a big scene and shocked everyone.”

Lillian had one more brush with the law, says area resident Carmel Nance, who knew her in her later years. In the 1950s, while driving along Georgia Avenue near Silver Spring, Maryland, she was involved in a car accident. When police examined the wreck, they found a packet of heroin. She was sent to a hospital at Lexington, Kentucky, where she underwent treatment for the addiction that had plagued her since childhood.

Lillian spent her last years in a retirement home in NW Washington. The Georgetown University Hospital physician who cared for her in the early 1980s said she spent most of her time staring out of her bedroom window in silence. He did not know her history. In fact, she was a puzzle to him: On the surface, she looked every bit the “sweet little old lady.” But, her body, on physical examination, bore unmistakable signs of past physical and chemical abuse.

She never left the nursing home. Lillian Alice Callahan died in November of 1984, at the age of eighty-six.

© Cecily Hilleary, 2009