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A Woman of Her Convictions

U.S. Attorney Leslie Caldwell has nailed some of New York’s most vicious criminals.

By Amy Aldrich

On the morning of Feb. 26, 1988, Edward Byrne, a 22-year-old New York cop, sat alone in his patrol car outside the home of a witness he was guarding. The rookie officer did not have long to live.

From a jailhouse telephone in Brooklyn, Howard "Pappy" Mason, 31, a hardened gang leader and drug dealer in prison on a weapons charge, had delivered a message to several members of his gang: He wanted a police officer dead. Byrne was the victim, shot in the head five times at close range by four of Mason’s thugs.

It fell to Leslie Caldwell, JD ’82, an assistant U.S. attorney in Brooklyn, to prosecute Mason and his co-defendant, Lorenzo "Fat Cat" Nichols. Caldwell had been a prosecutor for only two years. She inherited the Mason proceeding by default, when a senior prosecutor was pulled away from it to work on another case. The pressure to make sense of a mountain of evidence and to obtain a conviction was intense. "The case that made me grow up as a trial lawyer was the Pappy Mason murder trial," she says.

Today, almost 10 years after the trial she describes as her defining moment, Caldwell, a tall woman with dark brown hair and an engaging smile, seems totally at ease in her large corner office overlooking Brooklyn and the Verrazano Bridge. Her desk overflows with paperwork from cases in progress. A chair against the back wall holds stacks of press clippings detailing convictions she has won against drug dealers and gang leaders from Queens to Chinatown.

In 1994 Caldwell received the highest award given by the Department of Justice for criminal trial work. That same year, she was appointed to establish the Violent Criminal Enterprises Section of her office. She headed the unit until June 1997. Recently Caldwell was on the short list of federal prosecutors considered for the Oklahoma City bombing trial.

Back in 1989, Caldwell was so obviously green that the judge hearing the Mason case told her she was too inexperienced to handle it. A woman of quiet but steely determination, Caldwell set herself a goal: "to do the case and not panic." When the pressure became too intense, she would go for a run. Before making her opening statement, she "took a little walk, by myself, and watched the skyline."

In preparation, Caldwell had listened to thousands of FBI wiretaps, straining to find the evidence she needed to convict. Among the obscenity-laced conversations was one that Pappy Mason had with a member of his gang shortly after the Byrne shooting. The sound was fuzzy, but Mason seemed to be asking if "they" had arrived yet—referring to Byrne’s assassins, Caldwell suspected. This meshed with statements from several of the killers who, convicted by a state court, had agreed to cooperate with federal prosecutors.

Originally Mason faced narcotics and racketeering charges. After listening to the tapes, Caldwell made the decision to go after him for Byrne’s murder as well. "I felt like we had to win the murder case," she recalls.

Caldwell came through. The jury, deliberating for 13 hours, convicted Mason of ordering the execution of Edward Byrne. (In a separate trial, she had Lorenzo Nichols put away for ordering the murder of his parole officer.) The conclusive evidence for the jury was the snippet of conversation Caldwell had caught, together with testimony from the four cooperating gang members. Now in his 40s, Mason is serving a life sentence. Shortly after his conviction, he put out a contract on Caldwell. She makes light of it, but a colleague, Margaret Giordano, says the threat was serious. In 1990, another federal prosecutor, Giordano notes, received a package containing a briefcase with a loaded rifle, rigged to fire on opening. By chance, two visiting officers stopped her just before she popped the latch.

For Caldwell, the Mason trial began a seven-year stint prosecuting violent, often gruesome crimes. She was lead counsel in the trial of a defense attorney charged with murder, robbery and drug trafficking. She was sole prosecutor in a corruption case in which state officials were accused of peddling information to drug dealers. She persuaded five people involved in the murder of a parole officer to plead guilty. She tried the man who sent her colleague the booby-trapped briefcase. And she saw to the conviction of Gerald "Prince" Miller—an evil person, she says —who headed a Queens crack-dealing gang known as the Supreme Team.

Caldwell, a native of Pittsburgh, says she has no idea what attracted her to violent crime. Becoming a lawyer, however, had been her goal even in childhood. She attended GW Law School primarily because she envisioned a political career, but after three years in Washington she realized politics was not for her. "It feels like a big game that everyone’s playing," she says.

She had visited New York in high school and "loved it." Foreseeing a life as a partner in a large firm—"with a second house in the Hamptons"—she accepted an offer from a major New York firm, but found the work dull.

In 1987, she moved to the U.S. attorney’s office in Brooklyn. Doing "God’s work," as she laughingly refers to it, energizes her. "This job focuses you more," she says. "It’s important to do the right thing in the right way."

Out of court, Caldwell is casual, direct and friendly. An avid reader of novels and tales of adventure and endurance, Caldwell also rollerblades, hikes and plays golf—an abiding goal is to consistently break 90. She has climbed to the top of Mt. Whitney, the tallest peak in the continental United States, and trekked in New Zealand.

She has two brothers and admits to being highly competitive. Occasionally she finds herself competing just for the sake of competing. But most of the time she employs the trait productively—in court, for instance, where she uses a low-key approach to snare her victims. "I like to lull my adversaries into a false sense of security," she says with a grin. "I like to set traps."

A clever strategist, she has an unassuming manner that appeals to juries. She is also relentless. "She is very tough, very focused, like a dog biting your leg," says Gerald Shargel, a New York defensive attorney who has been on the other side of the courtroom from Caldwell many times.

"Leslie is an incredibly tough prosecutor," says Lawrence Schoenbach, a New York defense attorney in the Supreme Team case. "She beats the pants off of me. And she’s not just bright in an intellectual way. She has a sense of street smarts. She understands how life goes outside the courts."

Several years after prosecuting Howard Mason, Caldwell joined the push to clean up crime in Chinatown, a district of long, narrow streets crowded with restaurants and small grocery stores. Gang violence had been rampant there for years. Sometimes, at night, snipers from rival groups would fire at each other from rooftops, occasionally mowing down innocent bystanders. "It was very unsafe to be on the streets of Chinatown at 9:30," Caldwell notes.

Chinatown was run by tongs, purportedly legitimate business organizations that also engaged in racketeering and promotion of gang violence. While some gang members had been tried and convicted for their offenses, tong leaders had eluded prosecution.

In February 1992, three members of the Tung On Boys -- a gang that controlled southeastern Chinatown—burst into a Greenwich Village pool hall popular with a rival organization. The "boys" opened fire, killing a young honors student, James Rou, who had no gang connections whatsoever. The assassins were arrested and convicted in state court. While in jail, two of them revealed that Clifford Wong, a prominent tong leader, had ordered the pool-hall raid.

Working day and night at the end of 1994, through Thanksgiving and with only two days off for Christmas, Caldwell and her colleague Margaret Giordano amassed enough evidence to persuade the jury of Wong’s guilt. Even so, Wong seemed "amazed at the fact that he could be brought into court and before a jury," Caldwell says. In a related proceeding, she presented such a forceful case that Wong’s associate, Paul Lai—a respected businessman who had once been an adviser to former New York governor Mario Cuomo—agreed to a plea bargain.

"Leslie has a real ability to strategize, to play one thing off another," says Giordano. "She has a distinct style, a weird hybrid of forceful argument with little logic games—drawing things out to the absurd."

Tongs still operate, but it is now possible to dine at a Chinatown restaurant at night without worrying that gunfire might interrupt a meal. In the first 10 months of 1997, Caldwell notes, there was one homicide in Chinatown. In the previous years, there had been dozens.

Caldwell and other federal prosecutors have helped make the city safer because they have gone beyond attacking street crime. "The cases are getting bigger and bigger," Caldwell says. "We are not saying no to ambitious cases that really focus on the top people, like John Gotti."

Since 1997, Caldwell has largely turned her attention from violent offenses to white-collar corruption. "I need variety," she says.

With the boom in the stock market, fraudulent securities schemes have mushroomed, costing unwary customers tens of millions of dollars, according to Caldwell. In her office, she says, there are seven or eight pending securities cases, but "we could easily have 100." Long Island, in particular, houses a number of these illicit operations.

In a typical scam, shady brokers buy large quantities of worthless stocks, then pump up their value, using high pressure sales tactics. To hype the stock, these brokers sometimes recruit a sales force from off the streets. They assign them impressive phony names, hand them telephones, and put them to work calling prospects.

One strategy is first to sell customers a solid stock, such as IBM, then try to interest them in the worthless securities. Investors who fall for it find themselves with large holes in their pockets. Caldwell believes these office crooks to be as reprehensible as any other criminals she has encountered. "They really have no moral substance at all," she says.

Although she has no immediate plans to leave her job, Caldwell does seem intrigued at the possibility of testing her mettle in a different line of work. Women lawyers, she believers, generally are treated as equals in all branches of the profession—with one notable exception. "Very few are criminal defense attorneys," she says wryly. "It gives me a little pause."

Attorney Gerald Shargel agrees. "To a large extent, criminal defense work is one of the last strongholds of sexism," he says. "There is a certain machismo element to the practice."

Both Shargel and Lawrence Schoenbach say they would welcome Caldwell to their specialty. "I hope that five of 10 years from now someone will be going a profile of her as a prominent criminal defense attorney," Shargel says.

Amy Aldrich is a free-lance writer living in Washington.

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