40 Under Forty Feature – Jonathan Amarilio

Interviewed by Kenny Matuszewski

Now celebrating its 20th Anniversary, the Chicago Daily Law Bulletin’s 40 Under Forty recognizes rising stars in the legal community. Past winners come from all practice areas and settings, including the government, private practice, and in-house. The one thing they all share is their commitment to excellence and dedication to the legal profession.

Law is often regarded as one of the loneliest professions, but it does not have to be cloistered and isolating. In fact, law can be one of the most collaborative and communal of professions. By getting involved, making friends, and fostering connections, Jon Amarilio discovered this truth and was able to hone his abilities, grow his network, and rise to the top of the legal profession in the process.

Jon’s journey had a rocky start. Like many graduating from law school around the Great Recession, he was unsure of his immediate job prospects, much less his career path. He returned to Chicago after nearly a decade living in other cities, like Washington D.C. and Barcelona, Spain and took a clerkship in the chambers of Judge James R. Epstein, and later Michael B. Hyman, in the General Chancery Division of the Circuit Court of Cook County. Jon then took another clerkship with Justice Epstein when he was elected to the Illinois Appellate Court (Justice Hyman was elevated to the same court soon thereafter).

At first, Jon treated his legal career like a job, working hard while at the courthouse, but leaving work behind at the end of each day. That changed when Justices Epstein and Hyman (the latter a former CBA President and Editor-in-Chief of the Record) stressed to Jon the importance of getting involved in the legal community. They recommended that Jon join the Chicago Bar Association (“CBA”), particularly the Young Lawyers’ Section (“YLS”). As Jon soon discovered, taking that advice would be one of the best things he could have done for his career.

With Jon’s appellate clerkship coming to an end, J. Timothy Eaton, another former CBA President and then head of appellate litigation at Shekfsy & Froelich Ltd., recruited Jon to join the firm as an associate. Meeting Tim changed the trajectory of Jon’s career. Tim mentored Jon, taught him how to be an effective appellate litigator, and became one of Jon’s best friends. Thanks to Tim’s guidance, Jon excelled at Shefsky, and soon after the firm merged with Taft Stettinius & Hollister LLP in 2014, Jon became a partner in just his fifth year of private practice.

As a former president of the CBA, Tim encouraged Jon to get even more involved with the YLS and CBA than he already was, particularly in its governance. Jon did so, joining numerous boards and committees, and eventually rising to be Chair of the YLS. This involvement not only allowed Jon to meet and befriend many of Chicago’s best and brightest lawyers but also to boost his personal brand and build a book of business.

Jon now co-chairs Taft’s appellate practice group, in which he focuses his practice on appeals, critical motions in trial courts, and advising trial attorneys on the law and strategy in particularly complicated cases.

Practicing appellate law is rare. Most appellate lawyers either work at large law firms handling internally generated appeals or are solo practitioners. Jon and Tim are different. They work at a large law firm, but have their own appellate books of business and do not rely on internal firm work. That is even rarer. It allows them a measure of independence but, more importantly, it allows them to objectively assess the strengths and weaknesses of cases that are brought to them and to advise their clients and trial counsel frankly on whether and how to proceed. Doing so, they work regularly with trial counsel for both sides of the bar in everything from personal injury disputes to large business and governmental disputes, representing the side they believe to be in the right.

In 2018, Jon won the 40 Under Forty award as a young partner. His first and most overwhelming reaction to winning was not pride, but gratitude, thanking Adam Hrejsa, Editor of the Chicago Daily Law Bulletin, along with his co-counsel, opposing counsel, and clients who wrote letters supporting his nomination.

When asked what he thought led him to win the award, Jon said his involvement in the legal community and bar associations like the CBA was important. Apart from the CBA, for which he is now a board member, Jon is the Treasurer of the Appellate Lawyers Association, a board member for the Lawyers Lend-a-Hand-to-Youth foundation and serves on the Illinois Supreme Court’s Character and Fitness Committee. None of that, he thinks, would have been possible were it not for his CBA involvement.

And herein lies an irony. While involvement in bar associations is a critical component in the successful careers of so many lawyers, bar associations across the country are shrinking at unprecedented rates. Young lawyers are deciding more and more not to join bar associations because they believe their careers can flourish along other paths. Jon sees this as shortsighted. Involvement in local bar associations elevates the practice of law from a job to a profession; it allows attorneys not only to develop referral networks critical to their future security, but also allows them to develop friendships across firms, practice areas, and backgrounds. It makes the practice of law more fulfilling.

Using the initiative and work ethic that has helped him so well in private practice, Jon is hoping to draw the next generation of lawyers to the CBA, and to bar associations in general, through a newer medium: the podcast. In 2018, Jon and Jennifer Byrne, the YLS Director, launched the CBA’s @theBar podcast. Featuring guests like Ret. Judge Richard Posner, Amanda Knox’s defense team, the founder of Revolution Brewing, and the prosecutor who ended John Wayne Gacy’s serial murder spree, the podcast has grown exponentially and now has an international audience. Listeners appreciate Jon’s ability to connect with his guests, his quick wit, and his insightful questions.

When asked what he would tell a younger version of himself, Jon said he would tell his mid-twenties self that he knows less—much less—than he thinks knows. “True knowledge exists in knowing that you know nothing and succeeding in the law requires you to constantly learn and recognize previously unknown variables. Only by asking questions, rather than assuming you already have the answers, can you excel.”

When asked what, in his long list of accomplishments, Jon is most pleased by, his answer was not awards like the 40 Under Forty, or winning big cases, but the friendships he’s made along the way, particularly the opportunity to work with and befriend Tim Eaton. They have worked to affirm and reverse mega verdicts, they have tackled difficult constitutional questions, and case-by-case, they have changed the common law together, none of which would have been possible working alone. And so, it isn’t as lonely at the top as it seems, or at least it doesn’t have to be.

About Jonathan:

Jonathan Amarilio is a partner at Taft Stettinius & Hollister in Chicago specializing in civil appellate litigation and critical motion practice. In addition to hosting @theBar, Jon is a frequent author and speaker on a range of appellate topics. Jon is a former Chair of the YLS, has been recognized by Chicago Lawyer Magazine and Chicago Daily Law Bulletin as a “40 Under Forty” Illinois attorney to watch, and is regularly rated as a Super Lawyer and Leading Lawyer by those publications. 

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