Shah v. The System

Monica Shah had a plan. Fresh out of undergrad at the University of Pennsylvania in 2000, Shah took a business and consulting gig in New York City. Her carefully curated blueprint: Take a year or so to build a solid business foundation, get into law school, then spend her career sharpening a Big Law business litigation practice. 

Sept. 11, 2001, changed everything.

“I was at work in New York that day,” says Shah. “I had the direct experience of being somebody who saw what happened there, and then saw the aftermath. Obviously, this was a massive tragedy for the city and the country in terms of loss of life. I also saw a very quick shift in the targeting of people of South Asian descent and people who are Muslim for no reason other than their ethnicity and their religious background.”

Already accepted to Columbia Law, Shah pivoted. Hard.

“I asked myself what I wanted to do with my career, and it became clear that I wanted to focus on helping the vulnerable, particularly in civil rights and criminal defense work,” she says. “That’s the career I wanted.” 

And it’s the career the criminal defense and employment lawyer with Boston’s Zalkind Duncan & Bernstein has built. 

For the past 20 years, she has represented people across the entirety of the human spectrum. The common thread? Each is facing a powerful entity.

“I have empathy toward my clients, regardless of where they’re coming from,” she says. “I went in this direction to represent people who are in vulnerable situations, but that may mean that that vulnerable somebody is someone from the white-collar space or, in my university practice, a student or a faculty member. But they’re all facing the powers that be and a system that is stacked against them.”

During law school, Shah saw firsthand what it looked like to face a stacked deck. As an intern for the Asian American Legal Defense and Education Fund, she joined with community organizers and went door-knocking in predominantly South Asian neighborhoods. There, she witnessed the consequences of post-9/11 racial profiling: Stores were boarded up, people detained and families broken. “Our job was to go into these neighborhoods to give out ‘know your rights’ information to individuals that had been impacted by the kind of racial profiling that was decimating their community,” she says. “This opened my eyes to what lawyering actually is. It’s not just being in a courtroom. It’s providing the community with information about their fundamental, day-to-day rights.”

She credits several internships for pulling into “critical focus” what it means to be an individual ensnared in the criminal justice system. At Neighborhood Defender Service of Harlem, she interned for a public defender, then spent a summer with the NAACP Legal Defense Fund before interning for what is now Neufeld Scheck Brustin Hoffman & Freudenberger, doing wrongful conviction work.

“Many of my clients [at Neufeld] were exonerated through DNA evidence, but others were the victims of police brutality,” she says. She returned to Neufeld for three years after law school to focus on police brutality cases. “That work formed the basis for my criminal practice,” she says.

It was during her time with the NAACP, however, that Shah got to work on an amicus brief for Roper v. Simmons, in which SCOTUS held that it was unconstitutional to impose the execution of offenders who were under 18 when the crime was committed. Roper overruled 1989’s Stanford v. Kentucky, which upheld the death penalty for offenders as young as 16. The work changed the course of existence for 72 juvenile offenders across the nation who had been on death row. 

“What an amazing experience to work on an extremely important issue before the Supreme Court about the sanctity of a young person’s life, and the ability for young people to move forward,” says Shah, whose brief highlighted the racial inequities of the death penalty system. “I think that was critical to the decision in the case.”

At Zalkind, where Shah has been since 2010, her work is intentionally diverse, with cases split across criminal defense, employment, civil rights and Title IX matters.

Trial is the great clarifier, she says. “As you’re barreling toward trial, the strengths and weaknesses of your case come to the forefront. It’s exciting, and of course can produce a lot of anxiety. The way that I’ve dealt with it is the way that I think many lawyers deal with it: over-prepare. I think one of the benefits of my training at the firm and having the colleagues that I have is that we all support each other. If there is any superpower I have, it’s this amazing team.”

In 2015’s Charles v. City of Boston, Shah teamed up with colleague Emma Quinn-Judge for the first time. At the center of the employment discrimination case was a Haitian-American woman who had worked for the city’s treasury department for decades, who alleged she was discriminated against based on her race and denied opportunities for promotion to higher management positions. 

“This was a case we took mere weeks before trial,” says Quinn-Judge. “We hadn’t done the discovery, so we knew there were gaps. Monica was absolutely tenacious about calling up and talking to witnesses who really did not want to talk to us and thinking about ways we could strengthen the case that we hadn’t built a record ourselves.” 

One hurdle: Their client, a current employee of the city, appeared to have not even applied for the higher management positions she said she wasn’t getting.

“Our client had been sort of stuck at a certain management level for almost the entirety of her career, and she was never given the opportunity to apply for higher-level management positions,” Shah explains. “And our view of things—a view the jury agreed with—was that the city was trying to intentionally prevent her from applying for these management positions by constantly redrafting and updating the job descriptions.”

As a result, Shah and Quinn-Judge argued a “futility of application” theory, in which they would need to show that it was pointless for their client to even apply for positions, given what they viewed as the city’s intentional actions to bar her candidacy.

“Employment lawyers don’t typically take these cases because, if someone’s currently employed, they don’t necessarily have huge damages from termination, for example,” Shah says. “So we were operating on a very challenging theory.” 

Quinn-Judge remembers a moment when Shah was questioning the head of the treasury department. “She chose to cut off her exam at a point earlier than she thought she needed to, just because she thought the witness had left a really bad impression,” she says. “I think that takes real maturity and judgment as a lawyer, and lack of ego, to get to that point where you don’t just bang through your list for the sake of banging through your list.”

Their tag-team approach—Quinn-Judge on open, Shah on close, and a divvying-up on cross—worked to the tune of an almost $11 million jury verdict, which, despite being remitted by the trial judge, was upheld on appeal, ultimately reversing the remitter and requiring a reassessment of damages. “It really shed light on the continued discriminatory practices of the city, even well into 2015,” Shah says. 

“The thing about Monica is she’s very tough as a lawyer, and she always has been, and I suspect always will be,” says Quinn-Judge. “We grew up as lawyers together. What’s made her a great peer not just for me, but for others in our office, too, is helping us recognize where we need to grow and how we need to develop. She recognizes that it’s important not to stand still, and to keep moving and developing and growing and getting out of your comfort zone.”

She had a similar case last year, this time against the Federal Bureau of Prisons. Her client was a nurse manager who had worked for years at Fort Devens, a medical facility. Shah says the woman applied for a promotion and was denied in favor of a male nurse who was her subordinate at the time, and who had no relevant management experience. “It was just so obvious that she had been completely overlooked, and it was due to her sex and gender and also her LGBTQ status,” Shah says. “This really motivated me to take the case.”

Title VII, which applies to federal employees, carries a significant cap on damages. “It’s kind of difficult for the plaintiff’s bar to take a case where the cap is at $300,000,” she says. “But there was evidence of systemic discrimination and a difficult work environment there, and so I had to take it.” Counting emotional distress damages, back and front pay, attorney’s fees and interest, she won a nearly $1.2 million judgment.

“One of the things that’s most motivated my career is going up against powerful institutions, particularly in Massachusetts, where certain powerful institutions claim that they promote equality and that they care about diversity,” Shah says. 

By that token, Shah is proud of the time she’s dedicated lately to representing student protesters. While she declines to comment on the case, The Harvard Crimson reports Shah represented a pro-Palestine Harvard graduate student accused of assault at an October 2023 protest. 

“These years are a crucial time for young people who are trying to find their voices,” Shah says. “They’re out there protesting, and some are getting criminally charged, and it’s important for them to have representation and to make sure that their rights are being vindicated in criminal court. … Criminal charges can deeply impact [students], and they shouldn’t be penalized for expressing themselves and exerting their First Amendment rights. I view this work as essential in protecting fundamental freedoms.” 

Executive director of Lawyers for Civil Rights Iván Espinoza-Madrigal has partnered with Shah to protect those fundamental freedoms for the low-income people, people of color, and immigrants that LCR serves. 

“Monica was recruited to be on the board based on her tremendous leadership in Boston’s legal community, where she practices in a wide range of key areas that touch on the civil rights issues that my organization champions,” he says. “Monica joined the board and quickly made herself indispensable as part of the organization’s governance. … She brings fresh and incredible ideas to the boardroom. Oftentimes, we are called to action when there is significant uncertainty and when the stakes are high. Monica has an amazing clarity, vision and purpose that helps guide and lead in those challenging moments.”

Although he can’t reveal case specifics, Espinoza-Madrigal says Shah has handled many cases for the agency. “She is deeply committed to making sure that free legal services remain available for low-income people and other vulnerable communities,” he says. “What does having Monica at the table look like? It looks like having a fierce and fabulous advocate.”

Shah says her work, pro bono or otherwise, faces new challenges in 2025. “The rollback of diversity, equity and inclusion initiatives impacts the plaintiff’s side,” she says. Particularly for her employment work—she says the agencies that typically handle initial filings, such as the Equal Employment Opportunity Commission or the Massachusetts Commission Against Discrimination, have shifted priorities. 

“The EEOC is not taking on cases that involve transgender rights, for example,” she says. “They’re limiting or not taking cases involving LGBTQ rights.” As a result, cases that would typically be resolved at the agency level are now forced into court more frequently—if clients can find representation. “The biggest concern I have is: Are there enough lawyers out there that are willing to take on these cases?”

Another significant impact is in the pro bono space. “As big law firms are potentially not able to take on the pro bono work that they’ve taken on for decades [due to deals made with the Trump administration], it falls on smaller firms and solo practitioners to potentially fill in those gaps,” she says. At Zalkind, Shah says the firm continues to champion pro bono cases while acknowledging the challenge of filling large needs as a small shop.

The challenges also serve to remind Shah of the reason she pivoted on her path decades ago. 

“Going to law school and learning about the goal of the rule of law and constitutional and other civil rights means you’ve made a pledge to ensure that individuals are protected,” she says. “There is such power amassed by government, educational or corporate entities in the United States, and as that has developed over time, it’s become all the more important to focus on individuals. I truly feel it is my duty to do this work. It gives me purpose every day.”