Brennan was responsible for most of her own tuition and expenses; her résumé from this time includes “car jockey” at a rental outfit, cocktail waitress, magazine-subscription clerk and brewery worker. A journalism major, she also did stints at the Milwaukee Journal Sentinel—“My first front-page story was about a meth-lab bust,” she notes—and at a TV station in Green Bay before moving into an on-air slot in Eau Claire after graduation. Reporting gave her a buzz. “I enjoyed the ability to be in the moment,” she says, “to be a part of an exciting story, to try to interpret events and share them with the public.” Deciding it would be useful to develop a niche, she returned to the University of Wisconsin for law school.
“My grades were not stellar,” she said in a 2001 address to first-year law students at her alma mater; in the speech she also admitted to having gone through “periods of panic and gripping insecurity.” That insecurity was not in evidence by the time she landed in Frank Tuerkheimer’s Trial Lab class in the spring of her third year. “Bridget gave a closing argument as a prosecutor in a little mock trial that was close to brilliant,” recalls the professor, who recommended her to his former boss, then–Manhattan DA Robert Morgenthau. Although Brennan had grown up thinking of New York as a place with “no trees” and prosecutors as the “old guys” in the TV cop shows, a summer job in a legal clinic had piqued her interest in the work of the other side. “I came to realize the tremendous clout that a prosecutor had in terms of discretion”—deciding what charges to bring, she says. “And, frankly, I also realized that most of the people convicted were guilty of the crimes they were charged with. The question was whether the punishment was appropriate.”
Less than a week after the recommendation from her professor, Brennan headed to New York, where the cab ride from the airport confirmed some of her worst suspicions. “There was trash all over the side of the road and a carnage of cars,” she recalls of that 1983 visit. “I’m thinking, Where am I?”
“She was one of the best applicants we had that year,” says Morgenthau. As Brennan gained experience, the intensity of her cases ratcheted up. Robbery. Burglary. Sexual assault. Homicide. She began noticing a pattern: The late ’80s were “a really awful time, and every time you turned around, it was about drugs.” Especially crack cocaine. Those cases haunt her to this day. The addict parolee who robbed the restaurant manager who’d given him a job, severed the man’s neck with a machete and then smoked up all the money he had stolen. (“When I took a statement from him, he was weeping about having killed the man who had been so kind to him,” she recalls.) The crack-addicted mother who “never showed up” to testify against the man accused of sexually abusing her four-year-old girl.
“Everything I was seeing reinforced the devastation caused by this drug,” says Brennan, who took “a little breather” and transferred to the white-collar-crime unit, where the lawyers she supervised included the late President Kennedy’s son. “By that time my father had died,” she says. “But I’ve often thought that he would have loved it . . . [New York] is a remarkable city. The fact that Gale Brennan’s daughter could become John Kennedy Jr.’s boss is sort of an amazing quirk of fate.” Two years into her emotional respite, Brennan was offered the position of deputy chief of the Special Investigations Bureau (SIB) in the Office of the Special Narcotics Prosecutor. Here was an opportunity to attack head-on the evil at the root of so much of the despair she had seen. “I loved being on what I viewed as the front end of the problem,” she says, “seizing the drugs before they hit the streets, rather than on the back end, sweeping up the debris.”
When her supervisor downshifted to part time after a maternity leave, Brennan became the head of the SIB. Four years later, in 1998, she was sworn in as special narcotics prosecutor. She was pregnant for both promotions.