Justin Kaplan is a partner in Tressler’s HOA Practice Group. Justin’s practice includes representing condominium associations and common interest community associations in a variety of litigation matters, and counseling condominium associations and common interest community associations in interpreting governing documents and in pre-litigation disputes. Justin has a strong understanding of the intricacies involved in HOA governance, covenant enforcement, compliance, and dispute resolution. He is committed to providing practical legal advice that promotes harmonious relationships within communities while ensuring compliance with applicable laws.

Justin received his B.S. in Accounting from the University of Kansas’s Honors Program and his J.D. from Chicago-Kent College of Law, graduating with High Honors, where he attained the Order of the Coif distinction, the Dean’s Honor List every semester, the CALI Award, and served as a Student Bar Association Representative.

Where are you from?

I grew up in Kansas, but contrary to popular belief, I lived in a city and was nowhere near any farms. After college, I moved to Chicago, Illinois.

What was your first job?

My first job was working as a nanny for a family who were close family friends.

Do you have any hidden talents and/or unique hobbies?

I have always enjoyed collecting sports cards. Growing up, I have great memories of opening packs with my brothers, and it’s a hobby that has stayed with me over the years. Now that our kids are old enough, we’ve started collecting together. It’s especially meaningful—and a bit nostalgic—to see them enjoy the same pastime that I once shared with my siblings.

What is on your bucket list?

My family loves to travel, and we are always looking to take our kids to unique places. The Greek Islands are definitely on that list.

Why did you decide to become an attorney? 

My interest in the law was first sparked by my grandfather, who was an attorney. Spending time with him and being around the legal materials he kept at home ignited my curiosity. From a young age, I was drawn to the principle of “innocent until proven guilty” and the broader idea of fairness it represents. Although I do not practice criminal law, I have always admired that our legal system is built on protections that avoid presuming right or wrong, instead emphasizing due process. I knew I wanted to be part of a profession where I could help people navigate that system and protect their rights.

What does a typical workday look like for you?

With four kids, there’s no such thing as a “typical” day. My mornings start at 4:00 a.m. CT, allowing me to squeeze in a workout before meeting my wife for a CrossFit session. After that, it’s a hectic rush to get the kids ready and off to school. Once things settle down at home, I dive into work. No two days look the same, but most involve client meetings, court appearances, drafting legal filings, and addressing unexpected issues that come up. My evenings are just as packed as my wife and I coach our kids’ sports events and cheer them on. We then wind down together at home and spend some time with our puppies!

Why did you choose your areas of practice? 

My main concentration is on HOA/Condominium & Common Interest Community Association law. I find this area rewarding as it allows me to assist clients in navigating a realm that can often seem complex and overwhelming. With detailed governing documents and intricate statutory requirements, clients frequently seek clear and practical guidance. I take great satisfaction in bringing clarity to these issues and helping communities operate more smoothly and effectively.

What do you like most about Tressler? 

I appreciate that Tressler combines a national footprint with the feel of a close-knit family. Everyone is welcoming and always willing to lend a hand wherever needed. It’s a team of great people doing exceptional work.

What are you most proud of, professionally and/or personally? 

Professionally, I’m proud to have earned the trust of my clients and to know that they value the quality of my work and rely on me to guide them through their legal matters. Personally, I’m most proud of our four children and the opportunity to watch them grow, discover who they are, and develop into their own unique individuals.