A Conversation With Tony Aiello, Retired Sidley Partner

As family lore has it, Tony Aiello was destined to have a future in the legal profession. At a young age, he recalls having a prophetic interaction with his Sicilian immigrant grandmother. Following a spirited difference of opinion, she declared, “Anthony, you’re going to be a lawyer one day.” Aiello also credits his father, a residential real estate broker who frequently worked with lawyers, as having an influence on his decision to pursue a career in the law. Through his dad, a young Aiello met several of those lawyers and those interactions, in turn, piqued his interest in both real estate and law.

His professional journey began in 1983, when he attended DePaul University College of Law. Initially uncertain about pursuing a career in Big Law, Aiello’s property law professor, a mentor and a Sidley alum, convinced him to interview at the firm.

While he tried a few other top firms on for size as he made the round of interviews, Aiello recalls Sidley towered above them. “It was by far and beyond the most impressive, as well as the firm that I felt the most comfortable at. As a recruit, it was the people and the firm culture I saw on campus, and my interactions during my call back interviews, that attracted me to Sidley. These are intangibles that cannot be portrayed on a website or in marketing materials. Sidley has many lawyers who stay their whole careers at the firm just like me — from summer associate until they retire — which is a testament to the truly excellent culture.”

Aiello’s career at Sidley spanned nearly four decades. He began as a summer associate in 1985, joining the firm a year later as an associate. Achieving partnership status in 1994, Aiello ultimately led the firm’s Chicago Real Estate practice from 2012 until his retirement in December, 2021. His practice focused on real estate transactions of all types including purchases and sales, leasing, development, and financing transactions, with advancements in technology and the industry over the years contributing to the complexity of the work, as well as the size of the transactions.

“I’m very proud of the level of sophistication and professionalism of the Real Estate practice, both locally in Chicago and nationally,” he says, adding: “I believe we were one of the best real estate transactional practices in the country.”

Aiello’s favorite part of his time at Sidley was discovering new talent as one of the firm hiring partners and co-chairs of the recruiting committee. “No matter how far removed I was from being a law student or a first year associate, it kept me in touch with what was important for the next generation of legal minds. I had a strong commitment to promote the firm’s culture and find the best people. Seeing a recruit have success and perhaps become a partner or the head of a practice made me feel so proud as I really felt as though I was helping to shape the future of the firm.”

Aiello had several people he considered mentors at the firm and credits each of them for assisting in the development of his career; among them, former partners Ginny Aronson, Bob Maganuco, Paul Monson, Tony Licata, and Bruce Bernstein.

Aiello credits the decision to retire at the end of 2021 to the birth of his first grandchild. “That was when the light bulb went off.” He knew he wanted to be actively involved in his granddaughter’s — and later, grandson’s — life.

The legacy of practicing law continues, with Aiello having passed on his love of the profession to his children. He has a son and three daughters, two of whom are lawyers. His daughter Nicole Aiello Martinez, is now a senior managing associate at Sidley in the M&A and Private Equity practices. “Nicole was old enough to see how much I enjoyed my time at Sidley, and how much I respected the people I worked with. Obviously, I just think it’s a win-win for her to be practicing at Sidley. The firm’s getting a great lawyer, and she has a practice she loves while experiencing the same joy I had in my career.”

Aiello has fond memories of his colleagues at the firm, some of whom he still sees from time to time. “My practice group was very close, and we’re still good friends. There’s times when I get a phone call out of the blue from one of the partners who wants to talk about college football or some other topic. Somebody will retire or have a birthday, and we’ll try to set something up to get together. Sidley is still very much an important part of my life, whether I’m there every day or not.”

Meanwhile, Aiello is also busy with his family. During the winter, he and his wife of 40 years, Marie, go ice-skating and snowmobiling. In the summer, they enjoy boating, while the autumn brings the joy of hunting with his dogs. “It’s a very busy, but fun retirement,” Aiello says.

Published December 2024

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