Meanwhile, Judith Weinstein was the youngest of five from a well-to-do Northwest Baltimore family. She was just entering college when her father’s eponymous drugstore chain entered a messy and devastating bankruptcy. Monaghan and Weinstein met via local politics, working on Carlton R. Sickle’s failed 1966 bid for the Democratic nomination for governor. The couple remains active in politics; Monaghan remembers riding her tricycle around the old Stonewall Democratic Club as a five-year-old. Her father worked for years as a city liquor inspector, then began running his own club, the Point, which has thrived in an unlikely location on Franklintown Road. Her mother works for the National Security Agency and says she cannot divulge what she does.
“I’m pretty sure she’s a secretary,” Monaghan says, “but for all I know she’s a jet-setting spy who manages to get home by five thirty every night and put supper on the table.”
The family settled in Ten Hills on the city’s west side and Monaghan attended public schools, graduating from Western High School ’s prestigious A-course and then attending Washington College in Chestertown, where she majored in English. By her testimony, she discovered two lifelong influences on the Eastern Shore -rowing and Whitney Talbot. A member of a very old, very rich and very connected Valley family, Talbot has a work ethic as fierce as the one instilled in Monaghan by her middle-class parents, and the two have long reveled in their competitive friendship.
Upon graduation, Monaghan joined the Star as a general assignments reporter, while Talbot-who had transferred to Yale and majored in Japanese-landed a job on the Beacon-Light’s editorial pages. But Monaghan’s timing turned out to be less than felicitous-the Star folded before she was twenty-six, and the Beacon-Light declined to hire her. Cast adrift, she relied on the kindness of family members to help her make ends meet on her meager freelance salary. She lived in a cheap apartment above her aunt’s bookstore in Fells Point and relied on her uncle to throw her assignments for various state agencies. It was in Kitty Monaghan’s store, Women and Children First, that she met her current boyfriend, Edward “Crow” Ransome. When she was twenty-nine, she fell into PI work and likes to call herself the “accidental detective,” a riff on Anne Tyler’s The Accidental Tourist.
“Does anyone plan to become a private detective?” Monaghan asks. “It’s not a rhetorical question. I suppose somewhere there’s a little boy or girl dreaming of life as an investigator, but everyone I know seems to have done some other kind of work first. Lawyer, cop. All I know is I did a favor for a friend, botched it royally, and then tried to help his lawyer get him out of the mess I created. When it was over, the lawyer pressed me to work for him as an investigator, then pushed me out of the nest and all but forced me to open my own agency.”
That lawyer, Tyner Gray, would end up marrying Tess’s aunt Kitty. Monaghan pretends to be horrified by this development but seems to have genuine affection for the man who has mentored her since she was in her late twenties.
Her agency, Keys Investigation Inc., is technically co-owned by Edward Keys, a retired Baltimore police detective who seems to spend most of his time in Fenwick Island, Delaware. (Asked to comment for this story, Keys declined repeatedly and would not respond to rumors that he has, in fact, met Monaghan in the flesh only once.) Monaghan appears to be the sole employee on the premises of the onetime dry cleaner’s that serves as her office, although she jokes that there are two part-time workers “who have agreed to accept their compensation in dog biscuits.” Those would be Esskay, a retired racing greyhound named for her love of Baltimore ’s best-known sausage, and Miata, a docile Doberman with infallible instincts about people. “If she had growled at you, I wouldn’t have let you over the threshold,” Monaghan says. “I’ve learned the hard way to trust Miata.”
The office is filled with Baltimore-bilia-the old “Time for a Haircut” clock from a Woodlawn barbershop and several Esskay tins. “People give them to me,” Monaghan says. “I’m not prone to collecting things.”
Has anyone ever commented on the irony that Monaghan, who sits beneath that “Time for a Haircut” clock, once had a most untimely haircut, in which a serial killer sliced off her signature braid? Monaghan shot the man in self-defense, but not before he killed a former transportation cop with whom she was working.
“I don’t talk about that,” she says. “I understand you have to ask about it. I was a reporter, and I’d have asked about it, too. But it’s something I never discuss.”
Okay, so life and death have been shot down as topics. What would she prefer to talk about?
“Do you think the Orioles are ever going to get it together? One World Series in my lifetime. It’s so depressing.”
Monaghan lives in a renovated cottage on a hidden street alongside Stony Run Park in the prestigious Roland Park neighborhood. That’s how she puts it, her voice curlicued with sarcasm: “Welcome to the prestigious Roland Park neighborhood.” The house continues the rather whimsical decorating themes of her office, with a large neon sign that reads “Human Hair.” What is it with Monaghan and hair?
“You’re a little overanalytical,” she counters. “One of the liabilities of modern times is that everyone thinks they’re fluent in Freudian theory, and they throw the terms around so casually. I don’t have much use for psychiatry.”
Has she ever been in therapy?
“Once,” she admits promptly. “Court-ordered. You know what, though? I’d like to reverse myself. In general, I don’t have much use for psychiatry and I thought it was bulls-t when they put me in anger management. But it did help, just not in the way it was intended.”
How so?
“It’s not important,” she says, reaching for her right knee, a strange nervous tic that has popped up before. “Let’s just say that it doesn’t hurt sometimes to be a little angry.”
Monaghan is speaking in low tones, trying not to awaken her boyfriend. Six years her junior, Ransome works for Monaghan’s father, scouting the musical acts that appear at the father’s bar. Ransome’s workday ended a mere four hours ago, at 4 A.M., while Monaghan’s day began at 6 A.M. with a workout at the local boathouse.
Monaghan and Ransom have been a couple, on and off, for more than four years. Do they plan to marry?
“You know what? You and my mom should get together. You’d really hit it off. She asks me that every day. Ready to experience the exciting life of a private detective?” She draws out the syllables in “exciting” with the same sarcasm she used for “prestigious.”
What’s her destination this morning?
“The most wonderful place on earth-the Clarence Mitchell Jr. Courthouse.”
And, truth be told, the courthouse does seem to be a kind of fairyland to Monaghan, who stalks its halls and disappears into various records rooms, greeting many clerks by name. But wouldn’t it be more efficient to work from her office? Isn’t most of the information online?
“Some,” says Monaghan, who also relies on an online network of female investigators from across the country. “Not all. And there’s a serendipity to real life that the Internet can’t duplicate. Do you use the library? For anything? Well, sometimes you end up picking up the book next to the book you were looking for, and it’s that book that changes your life. Google’s great, but it’s no substitute for getting out and talking to people. Plus, the courthouse is only a block from Cypriana. So whenever I come here, I can reward myself with a celebratory chicken pita with extra feta cheese.”
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