In his expansive legal career with Sidley, which spanned two decades, John Gallo has had the seemingly effortless ability to cultivate meaningful and lasting relationships with the people around him—whether it was with his colleagues, clients or professional contacts. Having since changed tracks to join a nonprofit, he now mines that wonderful reserve of personal connections in a role solely dedicated to the betterment of the Chicago community.
“Every day, I do whatever I can to raise the profile of the organization,” said Gallo, who left Sidley in 2017 to serve as CEO and executive director of Legal Aid Chicago, the largest provider of free civil legal services to people living in poverty in the Chicago metro area. “This means leveraging my ready-made connections to the legal and corporate communities, as well as essential social networks and cultural centers. There is a huge demand for civil representation among those living in poverty.”
Gallo leads a team of 150 full-time lawyers and staff members, some of whom have dedicated their entire careers to legal aid. Gallo says making the leap from corporate law has had its challenges. “A big part of the steep learning curve of this job has been understanding the nature of the practice and the types of cases that my colleagues do.” He also cites the garden-variety issues that come with the management role, including those related to HR, finance and operations, which are now all under his domain.
He says he harnesses in his current role the legal experience he amassed in the 20 years he was a partner at Sidley, where he represented clients in complex civil litigation matters and led internal investigations on behalf of parties from various industries. Gallo also held several key leadership positions at the firm, including serving as head of the litigation group in Chicago and as global co-leader of the firm’s white collar practice.
Gallo looks back on those years with Sidley’s litigation group as a humbling experience. “The lawyers are just outrageously smart — a combination of modest and intellectual titans. I basically worked off the backs of their talent, knowing that every issue in every case would be identified and addressed.”
It was the firm’s pro bono work that made its greatest impact on Gallo. In 2005, he was instrumental in implementing a major pro bono initiative for Sidley — the Capital Litigation Project, which ensures that inmates incarcerated on death row have access to high-quality legal representation. “I have a letter that I received from a client on death row in Alabama that is one of my most treasured possessions,” he recalled fondly. “In it, he talks about how the work of the firm has given him hope in the face of complete hopelessness.”
Of his current work, Gallo speaks proudly of Legal Aid Chicago’s high-profile victory for National Teachers Academy (NTA), a high-performing African-American public elementary school located in Chicago’s South Loop. Chicago Public Schools wanted to close NTA and build a neighborhood high school to accommodate gentrification moving south.
“We sued on behalf of the families to keep the school open and won. That’s the bottom line,” he said.
When not working, Gallo enjoys spending time with his family, friends and faith community. He also shares that he has an unhealthy relationship with Notre Dame Fighting Irish football. “It’s more like an addiction, which I actually wish I didn’t have,” he said. “But now I just accept that I have it.”
Published September 2019
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