Written by Gia Miller and Kayla Schmidt
Jason is the writer and founder of the cartoon “Teddy’s Friends” and its foundation, which donates teddy bears to hospices, orphanages and hospitals, among other charitable acts. He’s also a licensed real estate salesperson for Douglas Elliman. He returned for his second year to use his knowledge to better the community—and decide who’s the best.
Why did you choose to return as a judge?
I had a blast last year! Plus there were businesses last year that I didn’t know as well, so it gave me an opportunity to go into them and get to know more areas of the community that I was not as aware of. It was super fun.
Based on this experience, which reality show would you be best suited to judge?
I really like the Halloween and Christmas Food Network shows. I love the creative process when the contestants bring their ideas to life. And, of course, I love tasty food.
What stood out to you during the judging process this year?
I feel like we expanded more throughout Westchester, which was nice. It was a little bit more northern-centered in the past, but now we’ve expanded a bit farther. I think that when the magazine switched from Katonah Connect to Connect to Northern Westchester it was a really big turning point, and it’s been great to further build our community in the county.
Did you take bribes? Be honest…
I didn’t, but I did notice people starting to recognize me in certain places, and I noticed a bit of a friendlier vibe from certain people. I could sense there was a little bit of “above and beyond” treatments in some places, but no bribes.
What was your judging philosophy this year?
My main thing was not being stuck in what it was like last year, because that was obviously the first time we did something like this. This year, a lot of nuances were worked out, which made it easier for me to separate the two.
You’re going on the judge circuit. What type of contest would you rather judge?
Best dog costume or most delicious vegan chili?
Best dog costume. Dogs are so cute, and they bring a lot of joy to people. And to see them in costume is one of the best things in the world.
Best creative cocktail or most exquisite hula dance?
I don’t drink, so I’d say the best creative mocktail. There’s so much creativity that can go into it, and it would be neat to see who would make an amazing mocktail. It’s becoming very popular at many established restaurants.
Most creative excuse for being late or best secret handshake?
I take being on time very seriously. But when I’m late, I might as well go out with a bang.
Best misuse of a toaster oven or funniest dad joke?
Funniest dad joke. My son Colby and I love them. Here’s one he just told me: Why did the pasta not belong? It was an impasta!
This article was published in the January/February 2026 edition of Connect to Northern Westchester.
To view all 2026 Connect to the Best winners, click here.
Gia Miller is an award-winning journalist and the editor-in-chief/co-publisher of Connect to Northern Westchester. She has a magazine journalism degree (yes, that's a real thing) from the University of Georgia and has written for countless national publications, ranging from SELF to The Washington Post. Gia desperately wishes schools still taught grammar. Also, she wants everyone to know they can delete the word "that" from about 90% of their sentences, and there's no such thing as "first annual." When she's not running her media empire, Gia enjoys spending quality time with friends and family, laughing at her crazy dog and listening to a good podcast. She thanks multiple alarms, fermented grapes and her amazing husband for helping her get through each day. Her love languages are food and humor.
Kayla Schmidt
Kayla Schmidt is a sophomore at Horace Greeley High School. She is part of the newspaper and the SADD club, and she is also the co-manager of the track team. In her free time, Kayla enjoys spending time with her friends, family, and dogs, along with reading (preferably on the beach).
