Written by Max Chwatko
Katonah resident Brian Willingham is the owner of the private investigation firm Diligentia Group in Katonah, moved to the area in 2014 and feels deeply rooted in our local community.
Why did you want to be a judge?
A friend asked me to volunteer, and I couldn’t say no. It’s a fantastic way to give back to the community and celebrate the incredible small businesses that bring so much character and vibrancy to the area. Plus, who doesn’t want an excuse to dive into the local scene and discover new favorites?
What’s your professional background?
I’ve been a private investigator for 23 years and started Diligentia Group 15 years ago. My connection to this area goes way back. I grew up in Cortland Manor, but Katonah became home in 2014 when my wife and I moved our family here. She grew up in town and went to John Jay.
What perspective did you bring as a judge?
My work as a private investigator gives me a unique lens. I’m not quick to judge—I weigh both sides, find the facts, and take my time forming an opinion. People have wildly different tastes and preferences, and I think it’s important to keep that in mind. While I have my own take on things, I’m generally more focused on fairness and balance.
What did you expect as a judge?
I looked forward to working in a collaborative environment where we could all find common ground. In a world full of divisiveness, it’s refreshing to agree on something, even if it’s just a local business.
What kind of judge are you?
I see myself as reasonable and reserved. I’m the guy in the middle, helping bring people together and forming a balanced opinion without being overly loud or forceful. Quiet but effective, I’d like to think.
Which famous judge best matches your personality?
Ruth Bader Ginsburg. Not that I can hold a candle to her brilliance, but I admire her quiet strength and thoughtful presence. She didn’t speak unless it mattered, and that’s something I strive for.
Last question: Who would make a better judge, Beetlejuice or Wolverine?
I’m gonna have to go with Beetlejuice. He might bring some wild insights and play devil’s advocate in the best way.
This article was published in the January/February 2025 edition of Connect to Northern Westchester.
Max Chwatko
