What My Bootlegging Grandfather Taught Me

3 min readOct 28, 2021


Quiet and unassuming, Grandpa Popeye (as we called him after the cartoon), would pull his 1985 Cadillac up to the pine trees and park.

He visited us once a week. He had big hearing aids and a quiet voice but he was always a source of calm in our home. He was at our home for Easter and Thanksgiving every year, sharing with my mom how to make golumpki (known now as stuffed cabbage), as his Ukrainian mom had made.

While my dad was half Italian (from his mother), and had a temper at times, Grandpa Popeye was 100% Ukrainian and quiet. And a big mystery to me.

His wife, the love of his life, my grandmother Elsie, had died from lung cancer in the late 1970’s. She had been a smoker and her diagnosis came swiftly and cruely. It was too late for her to get treatment and she died within a few months.

Grandpa Popeye visited his sons weekly, bringing stories and babka bread. My mom loved to hear about the old country and about his love of ice skating on the Erie Canal, driving a trolley, or working at General Electric.

My mom, curious like me, managed to get out the one detail he did not talk about a lot. Or ever. Something buried in his past.

In the 1980’s, I was a kid and had overheard the word bootlegger but did not know what it was. As I got older, my career consisted of writing, blogging, and a lot of genealogy, my true passion.

I learned in school about the 18th Amendment, the Volstead Act, passed in 1919 and went out of favor in 1933. This caused the increase in the illegal production and sale of liquor (known as “bootlegging”), the proliferation of speakeasies (illegal drinking spots), and the accompanying rise in gang violence.

My grandfather was born in 1906. Simple math showed me he was in his 20’s during this time and this myth became a fact. My grandfather was a mysterious legend to me.

I did not dig deeper into this until recently. I really don’t know why except when I lost my dad to Alzheimer’s in 2016 and then my uncle in 2020, I needed more answers about the family.

But that’s when my trail grew cold. My grandfather’s Ukrainian last name consisted of 14 letters and 10 variations of the spelling of it, according to…




New England born- now living in the Midwest. Blogger, author, influencer, history addict and genealogist in training