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Not The Secretary, The Assistant, The Typist, The Helpmate

Even though lawyering is in her blood, in the male-dominated legal world of the 1970s, M. Natalie McSherry had to prove all the things she wasn’t before she could prove what she was

Published in 2015 Maryland Super Lawyers magazine

By Joan Hennessy on December 12, 2014


Long before M. Natalie McSherry was born, the man who headed Maryland’s judiciary dispensed with the notion of women becoming lawyers. The law, as written, simply did not allow it.

“We are not to be understood as disparaging the laudable ambition of females to become lawyers,” wrote the chief judge of the Maryland Court of Appeals in a Nov. 21, 1901, decision. “It is for the General Assembly to declare what class of persons shall be admitted to the bar. We have no power to enact legislation. … If the General Assembly thinks, at its approaching session, that females ought to be admitted to the bar, it can so declare.”

The general assembly declared it the very next year.

That judge? James McSherry.

More than a century later, the judge’s great-granddaughter waxes philosophic about her ancestor’s decision. He was a strict constructionist, she says, a lawyer with a reverence for the law as written. In that respect, they share more than a surname.

Known for representing doctors and railroads—contentious cases that put her in the courtroom—McSherry, 64, is a principal at Kramon & Graham. And for her, the law is more than a calling.

Not only was her great-grandfather chief judge of the Court of Appeals, but both her grandfather and father were lawyers. And among her father’s 12 children, four became lawyers. 

Law isn’t just a calling; it’s the McSherry family business.

McSherry was raised in Frederick, an hour from Baltimore. Now considered a bedroom community for both Baltimore and neighboring Washington, D.C., when McSherry was growing up, it was the sticks. And that wasn’t bad.

She and her brothers and sisters could get on bicycles on a Saturday and be gone all day. Their parents weren’t the least bit worried. All over town, they were recognized, and that meant they never got away with anything.

“Everybody knew, ‘Oh, you’re a McSherry. I don’t know which one you are, but you’re a McSherry,’” she remembers. 

Her father regarded himself as a country lawyer and believed that legal services should be available to everyone.

“There were times when people would show up at our house with bushels of corn or tomatoes or whatever,” she says. “And those were the legal fees.”

As Frederick was a farming community, such scenes, straight out of To Kill a Mockingbird, happened often. But while the town may have been an ideal setting, her parents worried about the quality of the high schools. They sent several of their children to boarding schools. In McSherry’s case, that meant Eden Hall in Pennsylvania. A classic Catholic institution equipped with stone buildings, serious academics and the disciplined sisters of the Sacred Heart, the girls arose each morning by six and knelt on the chapel’s chilly stone floor. McSherry remembers it as a solid education, a foundation that enabled her to move on to a noted liberal arts school, Manhattanville College in Westchester County, New York.

After college, it was on to study the family business. While her great-grandfather had come along when it was customary to apprentice under other lawyers, both her grandfather and her father had studied at the University of Maryland School of Law. She did the same.

At the time, women had stricter entrance requirements to get in, she recalls. Consequently, at graduation, many of the academic awards went to women, who were disproportionately at the top of the class. Over and over again, as the dean handed out the awards, he called the names of women.

“About halfway through giving out the awards, he looks up and he says, ‘How could you men let this happen?’ Afterward, we went to him and said, ‘You made it happen, dean.’”

The year she graduated, 1974, turned out to be a tipping point for women in law, says her classmate, Judge Lynne Battaglia of the Maryland Court of Appeals and chair of the editorial committee for the upcoming book, Finding Justice: A History of Women Lawyers in Maryland (April 2015). Before 1974 there were not as many women as men admitted to the bar, she says. “It was seen as a more aggressive profession … rooted in conflict.”

Throughout the 1970s, more and more women became attorneys—but men still dominated the landscape. Newly minted women lawyers were competing for their jobs. Women in law had to be tough and self-confident, Battaglia says. “None of us knew whether we would be able to get jobs.”

At Whiteford Taylor & Preston, McSherry found herself adjusting to a paternalistic workforce in which women previously served in subordinate roles: the secretary, the assistant, the typist, the helpmate. She had to be tough, but she had to be diplomatic, too.

“We had an office administrator who, on National Secretaries’ Day, put a rose on the desk of each of the secretaries—and mine,” McSherry says.

She told him it was sweet but asked, “Why?”

“Well, all the other girls got one,” he told her, “so I thought you should have one, too.”

“I understand your intentions and that was really sweet,” McSherry responded, “but do you see the disconnect?”

Then there was the matter of court appearances.

“When I first started trying cases, I sometimes felt like the other lawyers, judges sometimes, weren’t taking me seriously,” she says. “But that was, I figured, something I could use to my advantage. Because they would just assume that I didn’t know what I was doing. When I did, it was like the element of surprise.”

Early on, McSherry worked on the defense side of a complicated legal malpractice case. Her co-counsel was the well-known Brendan Sullivan of Williams & Connolly. McSherry describes working with Sullivan before Judge David Ross, who was “a stickler for the rules and very demanding,” as an intensive course on civil procedure. “Between the two of them, it was an amazing education,” she says.

Months before the case was to go to trial, she married and asked the law firm for a leave of absence. Her husband was a Marine and the couple would have to move as he changed assignments. She also wanted to raise the kids.

The head of the firm, Woody Preston, asked how much of a leave of absence she would need.

“Oh, about 10 years,” McSherry said.  She was serious.

As she remembers it, after his shock wore off, he said, “OK. I don’t think anybody’s ever done that before, but OK.”

Not everyone was confident that she was making a smart move.

“I never expected to see her again,” recalls Kathleen Howard Meredith of Iliff, Meredith, Wildberger & Brennan. “The idea that she would come back after that would have been unthinkable for me.”

It was uncharted territory for McSherry. Through that decade, while raising three children, she pointedly kept in touch with lawyer friends in Baltimore. She didn’t want anyone to forget that she was coming back—even as she privately worried. 

She told a fellow colleague, “Gosh, I don’t know how I’m going to get up to speed when I come back. I mean, I haven’t practiced in 10 years.”

Her friend responded, “What are you talking about? You’re a trial lawyer. You learn what you need to learn for each case anyway. And other than that, you are just talking to juries and you know how to do that. What are you going to have to relearn?”

As it turns out, there were procedural changes that she had to learn. Otherwise, the decade away had changed nothing. She returned to Whiteford and wanted back in the courtroom. 

Quickly, her practice focused on medical malpractice and railroad accidents. Upon her return, she tackled the February 1996 head-on collision of Amtrak and MARC (Maryland Area Regional Commuter) trains, which resulted in the death of 11 people.

It was high-profile, the kind of case that lands in the newspapers every other day. Before the year was over, The Baltimore Sun reported on the filing of more than $200 million in lawsuits coming out of the accident. It looked nasty.

“The two railroads got together and decided we’re not going to fight about whose fault this is. We’re just going to resolve the claims,” she remembers. “Three out of 28 claims went to trial.”

Long ago, McSherry came to grips with a fundamental truth of her profession: Even though she relishes a good court case, her clients think of her the way they think of dentists.

“Nobody wants to be your client when you are doing what you do best,” she says.  “They figure, if I have to have somebody, I guess I’m OK having you. But it is not pleasant for litigants. It is incredibly stressful for them.”

There’s no stress when it comes to her peers, however—they like having cases against McSherry, says her former law partner, J. Norris Byrnes, a retired circuit court judge who now presides over settlement cases. They know what to expect. “She’ll be upfront,” he says, “but she’ll be prepared, too.”

Although that doesn’t mean her fellow attorneys always agree with her. McSherry knows they don’t, particularly on the matter of expert witnesses. She’d like more stringent guidelines about who can be declared an “expert” in court. A case in point: One of her clients, a doctor, was sued over his handling of a neonatal crisis. In the doctor’s defense, McSherry put up experts from first-tier medical facilities in Baltimore. The opposing lawyer’s expert witness was a family practitioner from rural Pennsylvania who had no experience with a neonatal case of this sort, but was convincing enough on the witness stand. McSherry’s client lost. 

“My good friends who are colleagues on the plaintiff’s side would say I want to keep out more expert testimony. And to some extent they are right,” she allows, “because there is this ongoing debate in litigation about the quality or reliability, if you will, of expert testimony.”  

At times, the attorney on the other side of the table is Meredith, who warns her clients about McSherry. 

“You have to make sure your clients understand that, because she’s friendly, that doesn’t mean that she is your friend,” Meredith says. “She has a job to do. And she will do it well.”

Six years ago, McSherry decamped from Whiteford, Taylor & Preston, which she felt had become too big. A year ago a seat opened on the Maryland Court of Appeals—the very court where her great-grandfather served as chief judge. She applied but didn’t get the appointment. 

The family business is still going strong, and has found itself a new shareholder. McSherry’s son, Peter Naugle, recently passed the bar.

No doubt his mom will give him good advice.

“You put all of your facts in the best light you can put them in,” she says. “You don’t hide facts. You don’t play games with the facts. You assume the other side is going to do the same thing. When that happens … it’s really just a question of if you can persuade people that you’re right.”

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