This Side of Terminal 5

In late 2016, Fiona McEntee and her two children, Rose and Perry, breezed through O’Hare International Airport. The trio had just arrived back in Chicago after visiting McEntee’s family in her native Ireland. They deplaned, grabbed their luggage, headed to ground transportation, and exited through the doors in a matter of minutes.

It was that routine sequence that the immigration lawyer and founder of McEntee Law Group couldn’t stop thinking about weeks later when she found herself back at O’Hare in the thick of President Donald Trump’s travel ban. Dubbed the “Muslim Ban,” it took effect Jan. 27, 2017, and barred Syrian refugees and citizens from seven predominantly Muslim countries from entering the United States. After receiving a frantic email from the International Refugee Assistance Project that urged any lawyers who could to get to O’Hare immediately, McEntee and her younger brother and law partner, Ray McEntee, were among the first to arrive.

“We raced to the airport, picking up other lawyers on the way,” says Ray, managing partner of the firm. “It was just such a poorly rolled out executive order. There was so much confusion. I think it was probably intentional. There were so many people being swept up in it. ‘War zone’ is probably a pretty fair summation.”

“I’m getting chills remembering how scary that was for those people,” says McEntee, who quickly became the de facto media face of the attorneys at the airport. “We were trying to speak to the CBP officers that were there, and they had no idea what was going on, either. People were just showing up to collect their relatives and they were nowhere to be found. … We set up a legal triage area and an Iranian man approached us. He was terrified because his wife, a green card holder from Iran, was detained, along with their baby, who was a U.S. citizen. They’d been living in the U.S. for years and went to Iran to visit family, and now this woman and her baby were detained for no reason.”

Thinking about the detained baby stirred a fire. “I’m looking at the same corridor I walked with my kids just a few weeks earlier and I thought, ‘What a privileged position I’m in.’ But now I’m on this side of Terminal 5. I’m an immigration lawyer. I can go on TV and tell the world what’s happening here, and I can advocate for these people,” says McEntee. “It got a lot of media coverage, and people started swarming to protest. By the end of that evening, they had released all the people they had unjustly detained.”

For their work—six months of being on call at O’Hare and wading through an extra 2,000 emails per day—McEntee and others earned the Chicago-Kent College of Law Outstanding Pro Bono Service Award. But it was chaotic. “And I was trying to meet that chaos. I was doing every interview, litigating, organizing protests. It became unsustainable,” she says. “I learned a lot of difficult lessons during the first Trump administration. I was so angry. I was marching in the streets. I had to start therapy.” 

Now facing heightened chaos surrounding immigration in Trump’s second term, McEntee looks for balance. She turns off the news. She coaches her kids’ sports teams. She cozies up to the sound of her husband, Brian, on the ukulele. She’s still fighting, but she’s not marching. 

“It’s critical to stand up for what you believe in, to make your signs and hit the streets,” she says. “I haven’t done that this time because my work, day in and day out, is a singular act of protest.”

The daughter of entrepreneurial parents who owned several small businesses across Dublin, McEntee was fascinated with the concept of entrepreneurship. And working for her parents turned out to be great for her future career. “I swear, there’s nothing that prepares you more for being a lawyer than working a reception desk as a teenager in a busy salon on a Saturday—when people are running behind for nail appointments and trying to get a waxing in and their eyebrows tinted, and you’re trying to keep the peace,” McEntee says with a laugh. “I look for people with retail and hospitality experience in hiring because the skills are so useful: learning how to speak to people, learning how to calm people down.”

McEntee’s father, Bernard, with whom she would have animated kitchen-table conversations with as a child, might tell you she was destined for social justice. “I was always taking up for the rights of this community or the other,” she says, noting that her impassioned positions earned her the family nickname “Save the Whales.” “I grew up in Dublin in the center of a collective ‘we’ in which we believe society is about the greater good. Ireland is very small but quite progressive. … In Ireland, my dad, who was a Joe Biden-type in terms of politics, would be considered conservative.”

After becoming interested in U.S. law, McEntee arrived in Chicago in 2002 as an international exchange student at DePaul University College of Law. Drawn to classroom discussions and the feverish defenses her classmates gave, she was exposed to viewpoints she’d never considered. She was so smitten with Chicago that she returned to earn her J.D. from the Chicago-Kent College of Law. And when McEntee saw an immigration law class in a course booklet, she thought, That’ll tick the “Save the Whales” box.

“As soon as I was in that class, I was like, ‘Yeah, OK. This is it.’”

When she first arrived stateside, McEntee was young and idealistic. Since then, her notions of America have evolved. “If I was at home, seeing the way things are unfolding, I don’t know if I would’ve made the decision to come,” she says. “I think right now there are many would-be international students going, ‘I don’t know that I want to be in a place where I could express an opinion in an op-ed or and end up in an immigration detention center.’”

It’s those would-be immigrants, and the innovations they bring, that McEntee works to protect as part of her firm’s startup niche. Colleen D. Egan, a former president and CEO of the Illinois Science & Technology Coalition who focused on technology-based economic development throughout the state, has worked with McEntee on immigration reform and entrepreneurship. The two bonded over shared Irish roots. “When I started in 2020, 28 percent of the startups coming out of our state universities had at least one immigrant founder. In 2024, that number was 42 percent,” says Egan. “Not only do immigrants play such an important role in a lot of our jobs here in Illinois—whether hospitality, childcare, food services, construction and other sectors—but on the entrepreneurship side, the numbers are huge.”

Egan credits McEntee with helping “scores of people” not only come to the U.S., but progress from student visas to citizenship to entrepreneurship. Some have become “unicorns”—that is, privately held companies valued at more than $1 billion. “Fifty one percent of the unicorns in this country have at least one immigrant founder,” Egan says. “I don’t think people really understand the impact of limiting these workers from coming here; everybody’s been fighting for a startup policy for the last 20 years and nothing gets changed. But Fiona has lived this journey. I don’t think anyone understands it more than her. She fights for the innovation economy of this country.”

One of those people was her own brother, Ray, who confesses to being a typical little brother as the two grew up in Ireland. Now, they manage the firm together and live five houses apart.

“Fiona made her way through the U.S. immigration system one way, I did it the other way,” Ray says, noting that his sister handled his H-1B visa. “I came over on a work visa, met my wife, had a marriage-based green card, and then became a citizen. So we’ve been through the process in different ways. It’s very personal to us. It should be personal to every American, because immigration is part of their story.”

“Whenever we’re able to work together to enable immigrants to do what immigrants do—which is work really hard and contribute and try to make this country a better place—that’s a very big deal for us,” McEntee says. 

One such success story is that of Mert Iseri, a former Turkish international student who co-founded Chicago-based health care technology company SwipeSense. McEntee secured Iseri’s O-1 visa, for extraordinary ability, as well as his green card. “SwipeSense was acquired, which is a success, and they created a lot of jobs,” says McEntee. “Every case that we work opens up a life of opportunity—not just for our client, but also for others through the ripple effect of what they grow. There’s a lot of pride in being along for that journey.”

McEntee got started with O-1 visas when she pitched herself, then a brand-new attorney, to work on an extraordinary ability visa for a professional sports team. “I was definitely not qualified to do that, nor did I know a thing about this American sport,” she says. “So I taught myself, and eventually became the main lawyer for this team, doing their immigration stuff.” 

Now McEntee represents leading musicians, artists, and athletes in addition to her innovative entrepreneurs and U.S. companies. One example is Yulia Kuznetsova, an artist and Moscow native who sought to stay in the U.S. so she could continue painting matters deemed unacceptable in Russia. “I love the startup space, but the O-1 practice is really fun,” she says. “A big part of it is writing and storytelling and being selective about evidence, and thinking about how to put this big puzzle together in a really creative way that shows the client’s extraordinary ability.”

There’s also the pro bono work. In addition to taking on clients hurt by Trump’s travel ban in 2017, McEntee and the firm have handled cases stemming from President Biden’s 2021 withdrawal from Afghanistan—which she calls “a horrific evacuation that led to all sorts of ramifications.”

It was McEntee’s pro bono efforts that attracted Paulina Okreglak to the firm. A Polish immigrant and U.S. citizen, Okreglak was the second hire at McEntee Law Group, where she serves as a legal manager. “Watching Fiona continuously take a leading stance on what I believe is the right side of history with the ‘Muslim Ban’ and with Afghanistan, where we handled a lot of the parole applications, was so inspiring,” she says. “For Afghanistan, we were trying to get information from people whom we basically abandoned, and they had nothing: no resources, no food. Yet we’re asking for signatures because the U.S. government requires pages to be hand-signed in a war zone. Everything changes on a dime, and we must be there in really vulnerable moments. Fiona is so good at that.”

Okreglak marvels at McEntee’s memory. “She’s able to recall a random case that was in an email blast from the American Immigration Lawyers Association from 10 years ago. Lo and behold, I’m 10 pages deep in Google, and she was right. She comes at everything with such a level of empathy, and she doesn’t have it in her to quit. There has to be someone to stand up and push back right now, and I think that’s Fiona.”

One way she pushed back is via a children’s book called Our American Dream, which McEntee published in 2020 as a response to the family separations that occurred under the first Trump administration. 

“It got to a point where you’re speaking about immigrants in such a derogatory, dehumanizing way that you feel it’s OK to rip a breastfeeding child from its mother’s arms and separate them with no intentions of reuniting them. How can anyone think that’s OK?” McEntee says. “I started thinking about how I have a front-row seat to the most beautiful immigration stories, and I wish that other people could see what I see—because I am still optimistic, still. People need an opportunity to see what I see: that immigrants are not statistics or figures but human beings who live full lives. I thought I’d tell their stories.”

Then there’s her own immigrant story. “It is my superpower to do this work,” she adds. “You’ve gone through it yourself, and your core default is to empathize.”

After helping so many immigrant clients with their startups, McEntee recently launched one of her own: Nouvie. When McEntee turned 40, she and her sister-in-law, Faith, wanted to toast the occasion with a nonalcoholic wine that actually tastes good. The two couldn’t find one, so they set about creating it. The sparkling de-alcoholized wine is produced in Spain, but the founders are working on a second line to be produced in California. 

Consider Nouvie another act of balance to help McEntee counter whatever comes next. “Every day, it’s something new and terrifying,” she says. “National Guard deployments, mass deportations. People being taken off the streets by masked agents. We’re seeing change overnight, or from the president’s tweets. It’s hard for people who don’t work in immigration to really understand the depth of this chaos.” 

But that may be changing. Last autumn, McEntee watched as federal agents deployed tear gas in Old Irving Park during a Halloween parade. “They were trying to grab somebody, and people were there with whistles trying to stop it. The people of Chicago have been amazing. Us lawyers, we know we’re not alone. They’re our allies in defending human rights,” she says. “The amount of community and togetherness has been incredible. The activism, protest and support … it really gives me hope.

“There is a whole generation of young people going to law school to become immigration lawyers. Not finding it the way I did, but pointing and saying, ‘Hey, I want to do that,’” she adds. “I’m so proud of this movement. There is nobody you would rather have your back than a bunch of tree-hugging, bra-burning immigration lawyers. I’m hopeful for our country because of my colleagues who are fighting for it.”