It’s easy to look back at my great-grandfather—or even my great-great or great-great-great—and see them as “pharmacy history.” What feels strange is writing about my dad, who I still work alongside a few days a week, and thinking of his years of ownership (1991–2021) in the same way.

Over the past four Ozzie Gram issues, I’ve written about the first four generations of my family who ran the pharmacy. To now turn the spotlight to my dad, the fifth generation owner, feels a little different. His years don’t feel like history yet—they feel like yesterday. But working with our 2025 community partner, Naper Settlement, I’m often reminded that history is happening all the time. Even when it feels “too recent,” it’s still part of the story.

So, here goes: I’m going to write about my dad’s time at the helm just like I did the previous four generations—because it really is part of Oswald’s history! And I’m grateful he’s still here today, part of the pharmacy, part of my life, and part of my kids’ lives.

Like me, my dad Bill didn’t plan on running the family business. He was just “helping out” his dad when a longtime clerk retired. That temporary gig turned into more than 40 years at the family store.

Fourth-generation owner Bill Anderson restocking vitamins in the old Oswald’s Pharmacy location, December 1990.

By the 1980s, the bookshop my great-grandfather had opened in 1964, Paperback Paradise, had moved down the street and become Anderson’s Bookshop. They added a second store in Downers Grove (where Grandpa Kester, our third-generation owner, was born and raised) and even a warehouse in Aurora. My dad worked with his three siblings in those businesses, but he took on the pharmacy.

During the 1990s, Naperville was booming, and with every new subdivision came another chain pharmacy. Mom-and-pop shops across town started to disappear. My dad shifted our focus—cosmetics, once a huge department, gave way to toys and gifts. Thanks to a small Illinois company called Ty Inc., we got in on Beanie Babies at just the right time. That craze helped kickstart what became a much larger gift and toy department in the years that followed.

By 2004, my dad made the tough decision to move Oswald’s from downtown Naperville to Naperville Plaza. Downtown had become more about dining and shopping than services, and the Plaza offered twice the space. With the move, he grew our medical equipment department—something we’ve always carried in some form, but which he saw had real potential. He was right. The department grew so much that in 2015 we expanded again, adding 5,000 square feet to create our premier showroom.

By the mid-2010s, I had returned to the business myself—also just to “help out.” Like my dad, I quickly realized this was where I belonged. Together we navigated the challenges of the COVID-19 pandemic, and in January of 2021, we transitioned ownership.

I was asked on a recent podcast about how Oswald’s has managed to carry on for 150 years. My answer was simple: overlap. Each generation has worked side by side with the one before for at least five years. I’ve been lucky enough to work with my dad for over a decade, not to mention my high school days behind the counter. (Those stories are for another time!)

If you see Bill around the store, make sure to say hello—he swears he’ll retire one day, but we’re grateful for every day he’s still here. And don’t forget to join us for our 150th anniversary celebrations this month: a ribbon cutting on Friday the 26th and our big Customer Appreciation Day on Saturday the 27th with giveaways, sales, snacks, and more. We hope to see you there!