Two weeks before this interview, at 1:30 in the morning, Todd C. Pomerleau sat down to file a federal lawsuit on behalf of a pregnant trafficking victim. In roughly six hours, she was scheduled to be loaded onto a deportation flight. By the time most of Boston was awake, a federal judge had stopped the removal.

Pomerleau tells the story without any drama, the way other people describe clearing their inbox. Filing habeas corpus petitions in the dead of night has simply become the rhythm of his life. "I filed them at 1:30 in the morning. I filed them on Labor Day, wedding anniversaries," he says. "It's just around the clock." By his own estimate, he has been lead counsel on somewhere between 100 and 150 habeas petitions filed.

It is a punishing pace, and Pomerleau is clear-eyed about the cost. But the work has also placed him at the exact center of one of the defining legal fights of the moment. To understand how an attorney ends up litigating against the clock before sunrise, it helps to go back to a decision he almost did not make, long before he had ever read an immigration statute, when his plan was to be a working musician.

From Jazz Performance Major to the Courtroom: Todd Pomerleau's Unlikely Path Into Law

Pomerleau spent a couple of years at Arizona State University as a jazz performance major, a guitarist who used to joke that he had a backup plan ready. "I used to joke that if the band broke up, I'd go to law school," he recalls. "And there we are."

He grew up in Lewiston, Maine, and, after graduating magna cum laude near the top of his class, his first job out of law school sent him back home. He spent a year as a law clerk for Associate Justice Robert Clifford of the Maine Supreme Judicial Court, a coveted but demanding position. "You basically spend a year as a bookworm doing all the research for the opinions that the court's going to draft," he says, "helping all the judges prepare for oral arguments." During that year, he found himself gravitating toward the constitutional cases on the docket, particularly those touching criminal law and civil rights.

The clerkship is traditionally a stepping stone, and Pomerleau used it as one. He moved to Boston to become a full-time public defender, working a stone's throw from where his office sits today. The job was an education in how the legal system absorbs human crisis. "It's a lot of people that have mental health issues, abuse, you name it," he says. "In a lot of ways, you feel like you're a social worker." He came away with a conviction that has shaped his career since: "It seems like people just end up in criminal court because the rest of the system doesn't know how to deal with people."

Discovering "Crimmigration" Before the Field Had a Name

Some of the clients Pomerleau represented as a public defender had immigration issues tangled up with their criminal cases, and at the time, almost no one knew how to handle that overlap. "It was really uncharted water," he says. "There weren't a lot of criminal defense lawyers that even understood immigration law."

That changed when he left the public defender's office to work for an attorney named Jeffrey B. Rubin, who is now his law partner. Rubin spoke fluent Spanish and represented a large non-citizen clientele, and Pomerleau began absorbing the intersection of criminal and immigration law in real time. He had never taken an immigration course in law school. "I honestly didn't even comprehend what it entailed," he admits.

Rubin had been ahead of his time. Since the late 1990s, he had argued in court that a lawyer who failed to give a non-citizen proper immigration advice in a criminal case was violating the Constitution. Judges often dismissed the idea outright. "A lot of judges would just look at you like, what are you talking about? That's not the law," Pomerleau says. Massachusetts was firmly on the opposing side of the issue. Then, in 2010, the U.S. Supreme Court decided Padilla v. Kentucky and recognized for the first time that non-citizens are entitled, at a minimum, to accurate advice about whether a guilty plea will get them deported. Pomerleau then drafted an amicus brief in a 2013 case before the Massachusetts Supreme Judicial Court, Commonwealth v. Sylvain, that made Padilla rights retroactive to 1997 under Massachusetts law - a landmark decision to this day. 

Pomerleau and Rubin had been specializing in that hybrid practice before the law caught up to it. Today the field even has a name. "Harvard Law School literally has a clinic called the Crimmigration Clinic," he notes. "So I'm effectively a crimmigration attorney, and I've been one since the beginning." After building his own practice, Pomerleau Wood LLP, alongside attorney Danielle M. Wood, he partnered with his former boss to form Rubin Pomerleau PC.

Wescley Fonseca Pereira v. Sessions: The 8-1 Supreme Court Victory That Reshaped Immigration Law

Within a few years of forming the firm, Rubin Pomerleau had a case in front of the United States Supreme Court. Pereira v. Sessions was decided in 2018 by a margin of 8 to 1, and the firm litigated it alongside the corporate law firm Goodwin Procter. For Goodwin attorney David Zimmer, it was his first Supreme Court oral argument.

"It affected millions of people's lives overnight. It invalidated millions of notices that the government had been giving to non-citizens to start a deportation process going back to 1997."

The case turned on a single document called a notice to appear, the charging paper that begins a deportation proceeding. By law, that notice is supposed to tell a non-citizen where and when to show up for an immigration hearing. For years, Pomerleau explains, the government simply left that section blank, or wrote "to be determined." People missed hearings they never knew they had, and immigration judges ordered them deported in absentia.

Beneath the procedural language was a powerful consequence. A defective notice, the government argued, still triggered the "stop-time rule," a provision that freezes the clock on the continuous physical presence many immigrants need to qualify for relief from removal. The Supreme Court rejected that argument, and the majority reached for a memorable analogy. An incomplete notice, the Court reasoned, was not really a notice at all. As Pomerleau puts it, "You can't just put the fourth wheel on it and call it a car." The lone dissenter, Justice Samuel Alito, took the opposite view, describing the document as a three-wheeled Chevy that could simply have a wheel added and be driven off the lot.

A year later, Rubin Pomerleau received the prestigious Jack Wasserman Award, the only national award given by the American Immigration Lawyers Association for excellence in immigration litigation. It is voted on annually and recognizes the most impactful immigration case in the country.

Wescley Pereira: The Handyman Behind the Landmark Case

For all its national reach, the case began with one person. Wesley Pereira was a Brazilian handyman living on Martha's Vineyard, a caretaker for a roughly 100-acre property, a man who races motorcycles around a track on weekends. "Everyone knows him," Pomerleau says. "He'll give you the shirt off his back."

Pereira's ordeal started with a broken tail light. He was pulled over, detained, and during the process he told immigration officials that mail was unreliable where he lived and asked them to use his post office box. They mailed his notice to the wrong address anyway. Years later, he was arrested again and told he had already been ordered deported for missing a hearing he never knew about. He spent months in jail. The proof of the error turned up in his own file: a return-to-sender envelope.

By the time Pereira walked into Rubin Pomerleau's office seeking a second opinion, his business was thriving, he owned a home, and his US citizen children were growing up. He arrived discouraged. "I just remember him walking into our office kind of hanging his head low," Pomerleau says, "because his other lawyer was like, look, there's nothing we can do for you. You should just voluntarily depart the country."

There is one more turn to the story. Years of pandemic-era delays mean Pereira still has not received his green card. "He's like literally one of the only people in the country, I think, that hasn't even fully benefited from his own case," Pomerleau says. He expects that to change soon.

How One Ruling Rippled All the Way to Chevron

A Supreme Court win that broad does not end the litigation. It starts a new round of it. After Pereira, immigration courts across the country split over what the decision meant, and roughly 10,000 cases were dismissed within weeks. Pomerleau then argued Matter of Fernandes before the Board of Immigration Appeals, a body that holds oral argument only once or twice a year. That case established the remedy: a non-citizen who makes a timely objection to a defective notice can have the case dismissed.

The deepest ripple came from a single concurring opinion. In Pereira, Justice Anthony Kennedy wrote separately to question Chevron deference, the long-standing doctrine that courts should defer to a government agency's interpretation of an ambiguous statute. That concurrence was later cited by veteran Supreme Court litigator Paul Clement in Loper Bright, the case brought by a group of commercial fishermen that ultimately overturned Chevron. "Strange bedfellows," Pomerleau says of the alliances that immigration litigation can produce, since many of the judges most skeptical of unchecked agency power are also among the most conservative.

Filing Habeas Corpus Petitions Around the Clock in the Second Trump Administration

If Pereira defined the first half of Pomerleau's career, the work of the past year may define the rest of it. In the last twelve months, he says, he has handled eight or nine cases that became national or international news, and nearly every one started the same way: with a habeas corpus petition. He sits on a Boston task force called the Habeas Project, where he mentors other attorneys filing emergency petitions at all hours.

The cases he describes share a disturbing pattern. He represented Any Lucia Lopez Belloza, a 19-year-old freshman attending Babson College on a full scholarship, who was deported to Honduras, a country she had not lived in since she was eight, despite a federal court order barring her removal. She learned she had a lawyer only after she was already gone.

He represented two longtime lawful permanent residents detained at Logan Airport, each of whom had held a green card for more than 40 years. One was returning from a family reunion in Cancún. The other had traveled to Cape Verde to bury her brother and see her mother for the first time in four decades, and was held at the airport for two weeks. Neither was ever charged with anything. One of them, Jemmy Rosa, nearly died in detention, and her case drew a front-page editorial from The New York Times and Emmy-nominated news coverage.

He represented nine workers arrested in a single raid at a Boston car wash, none of whom had a criminal record, after a college Republican leader at a local university bragged on social media about having them detained.

"The People Following the Rules Are the Ones Getting Arrested"

Ask Pomerleau what connects these cases, and his answer is immediate. The clients are not, by and large, people hiding from the law.

"So many of the people are the ones that are actually following the rules. They're applying for their green cards, they're reporting crimes, they're showing up to testify in court when asked to. And then they're getting arrested, thrown in vans, and getting shipped out of the country with no due process."

That, he argues, is precisely why federal court matters so much right now. A habeas petition is often the only tool fast enough to stop a removal before a plane leaves the ground, and it does not always succeed. "A lot of it is just luck of the draw," he says, "on the timing of where your case is."

It is also why he now spends a meaningful share of his days talking to reporters, something he frames as part of the job rather than a distraction from it. "It's important to explain to the media what's going on with the government, because I don't think a lot of people believe it," he says. "They just think we're like these crazy immigration lawyers. It's like, no. It's that off the rails right now."

Mass Deportation Defense and a Nationwide Mobilization of Immigration Lawyers

Pomerleau has co-founded a nonprofit called Mass Deportation Defense with his former law partner Wood, which his firm sponsors at the gold level, an organization whose name is a deliberate inversion of the policy it exists to counter. He frames the past year as exhausting, but he is careful to name a silver lining too.

"There's been this unique mobilization effort nationwide," he says. He has collaborated with nonprofits, law firms, and law schools across the country, taken calls from members of Congress, and advised a major Washington nonprofit on pending legislation. "I've been meeting people I never would have probably met before."

He is also candid, with a quick disclaimer that he is not trying to brag, about why his firm has been able to take on so much. Rubin Pomerleau can litigate a criminal case, file a habeas petition, and carry an appeal all the way to the Supreme Court. "All the heavy lifting litigation that needs to be done, we've just been doing it for years," he says. "It just seems like what we are known for doing is exactly what is needed at this moment in history."

"You're Only as Good as Your Last Case"

The work of the second Trump administration, Pomerleau says, has been "exhausting and exhilarating at the same time." He files before dawn, fields interview requests from outlets like CNN, MSNow, and Telemundo when a case goes viral, and mentors younger lawyers learning to do the same. None of it has dimmed the urgency he brings to it.

What keeps him grounded is a refusal to coast on past victories, even one as large as a Supreme Court win. Asked to reflect on being called a legend in his field, he waves the word off with the instinct of someone who knows the next emergency filing is always coming.

"I try to be," he says. "But I'm always only as good as my last case."

It is a fitting close for a lawyer whose career has, again and again, placed him exactly where the law was breaking and someone was needed to fix it. From a clerkship in Maine to a courtroom analogy about a three-wheeled car, from one handyman on Martha's Vineyard to millions of invalidated notices, Todd C. Pomerleau has built a practice on a simple proposition: that the people moving through the immigration system are people first, and that someone has to be awake at 1:30 in the morning to remind the system of it.

This interview was conducted for the LegalBridge Magazine Immigration Leadership Interview Series, which spotlights the perspectives of leading immigration and global mobility experts.