Meet a Westside Pioneer!
John ‘Skip’ Sherbak

What kind of career have you had?
I was the section foreman for the Midland Terminal Railway from 1947 to 1949. I’d fill out the timecards and I repaired track. I was a boxer in the lightweight division in the late ‘40s and was also a bartender. I was in the Navy from 1950-54, and during the Korean War I served on the heavy cruiser, the Quincy. I recently retired from my own business of 50 years, Skip’s Mountain TV.

Can you tell us about your marriage?
Louise and I met in San Diego while playing skeeball. I was a sailor and she was a barmaid. We’re celebrating our 56th anniversary Oct. 23.

Did you have children?
We raised my brother’s three children (Bret, Mark, and Lisa) after he was killed in a car accident.

Grandchildren? Great-Grandchildren?
Bret had two children (girl and a boy). Lisa had a daughter.

Any of your family members still here?
My sister and Bret still live here.

Can you tell us about your parents/grandparents?
My father had been a bridge and building foreman with the Midland Terminal Railway (1926-1942). My mother was from Kansas and moved out here with her family during the Depression. My granddad and my grandmother owned a 360-acre homestead (which included land that goes up to Bear Creek Park). When they couldn’t pay the war and property taxes (they came to about $49 total back then, in the 1800s), the state took it over and then sold it to Bott, Hagerman and Howbert. I didn’t know my grandparents on my mothers’s side very well.

Skip and his wife Louise in the 1950s.
Courtesy of Skip Sherbak What are your best memories of growing up on the Westside?
Freedom. I could go rabbit hunting right out my back door and go deer hunting in Bear Creek Canyon. Bartending at the age of 17... (I had changed my birth certificate.)

What is gone from the Westside now that you wish had stayed?
The Midland railroad. The owners just tore it up after World War II to sell for the metal. It would be nice to ride that thing to Cripple Creek now. And, it would be a wonderful money-maker.

What has stayed that you wish had gone?
Everything that’s stayed is pretty good. I can’t think of anything.

How about the way things have changed? It’s still a small community compared to other parts of town. There used to be one policeman walking the Westside beat, going from bar to bar and store to store. We used to have a butcher shop, grocery store and a big pool hall just before Cunningham’s Bar. There used to be only one high school (downtown) and if I couldn’t get a ride I had to walk or take the trolley. Now there’s a high school on this side of town. We used to be able to fish and drink water right out of the creek. Now that’d be like committing suicide; it was a river then.

Baby Skip with his parents, John and Sarah Ann Sherbak, around 1930. 
Courtesy of Skip Sherbak Overall, is the Westside better or worse than when you were a kid here?
Better when I was a kid, because there are too many people now.

“Meet a Westside Pioneer” interviews people who were born, raised and still live on the Colorado Springs Westside. If you meet that criteria (or know someone who does), please give us a call at 471-6776.