The Dropped Stitch owner Hannah Wilson won over $230,000 appearing on Jeopardy in 2023. Her game-show winnings gave her and her wife Katie the financial freedom to move from their apartment in Logan Square to a condo in Andersonville—and turn Wilson’s love of knitting into a business venture.
Wilson, who learned to knit as a child and got back into it during the COVID-19 pandemic, discovered there wasn’t a yarn store within walking distance of their condo. She did the research about running a retail business, bought a vacant storefront and transformed it into The Dropped Stitch, 1524 W. Bryn Mawr Ave., in November 2024.
The name came from a common knitting mistake because she “was always dropping stitches when I knitted, and at first I would panic. But in knitting, pretty much everything is fixable and that really teaches you how a piece of knit fabric is put together.”
The Dropped Stitch has recently added a tiny secondhand bookstore called The Turned Page where Wilson sells interesting used books.
She hopes Dropped Stitch will illustrate for customers that, “Yarn is something you need to see and feel in person to know what you like.”
Wilson also does private knitting and crochet lessons. She said once people get the hang of it, they will have something to do with their hands while they watch TV for the rest of their lives, and be able to show off what they’ve made to the public.
Being on Jeopardy had long been a dream. Wilson made numerous attempts to be a contestant since her college years at the University of Chicago and finally got the chance in early 2023. Her episodes aired in May 2023, and she won eight games in a row.
“It was an absolute trip to be up on stage,” said Wilson. “When I won the first game I really had no time to think about it, because they tape five shows a day and I had to immediately get changed for the next taping. All eight games I won were taped within a 48-hour period, but of course you’re not allowed to tell anyone about it until they air, which was almost two months later.
“It only really hit me once I got back to Chicago [that] I was going to be on TV every day for almost two weeks. I was actually kind of nervous about it, because I knew trans people often get a lot of hate just for existing in public, and I knew if certain right-wing culture warriors decided to target me they could make my life hell. Luckily, it didn’t really happen. I don’t think I won enough games to attract the notice of non-Jeopardy fans. In the end, I got a lot more positive feedback than negative stuff.”
Wilson’s victory made her the second out trans woman to win at Jeopardy after Amy Schneider’s 40 consecutive game win from November 2021 to January 2022. Wilson had actually connected with Schneider before her Jeopardy appearance because they were both members of the LearnedLeague trivia competition website and sought out her advice about being an out trans woman in the public eye.
Schneider eased Wilson’s fears, which gave her the confidence to try out for the show again after transitioning.
“I don’t think I would have been willing to try out for Jeopardy again after my transition if she hadn’t done it first,” Wilson said. “I finally got to meet her in person, and do karaoke with her, at the 2025 Jeopardy Invitation Tournament. She’s the best.”
Wilson’s journey began in California’s Bay Area, where she spent her childhood and teen years. She moved to Chicago in 2006 to attend college. Wilson got her bachelor’s degree in geography.
While in college, Wilson began working at the NORC research organization, where she stayed through 2017. She quit because she got burned out and, “Donald Trump was elected president, and I guessed a lot of the funding for this stuff was going to dry up.”
A couple of years later, Wilson realized she was trans and wanted to medically transition. A new job at Strata Decision Technology gave her the insurance to “finance my transition while working from home due to the COVID-19 pandemic.”
After Wilson’s Jeopardy victory, she quit her data scientist job at Strata Decision Technology. She “had completed all of my medical transition goals,” which was one of the reasons she kept working there, to help pay for those medical costs.
Wilson met Katie in 2017 on Tinder and their first date occurred at Katie’s friends graduation party. Katie’s friend officiated their wedding in September 2022 at the Music Box Theatre, because both of them are movie fans. The couple recently welcomed their son Felix (via surrogacy) whom they call “absolutely perfect. We can’t wait to see what kind of person he turns out to be.”
They both love living in Andersonville because it’s quieter and closer to the lake. For Wilson, the neighborhood “is probably one of the best places in the country to walk around as a transgender lesbian without attracting any attention.”
Wilson spends most of her time outside of work with Katie and Felix exploring all Chicago has to offer, meeting with friends and their children, playing her electronic keyboard, reading books and “of course I still watch Jeopardy every single weeknight.”
On Nov. 13, Wilson will hold a second anniversary party for The Dropped Stitch. Last year’s event “was an absolute blast” with snacks, cake, drinks, balloons and a big sale. She said the store was packed that day and they plan on holding an even bigger event this year, “So stay tuned.”
