Leo Castle

Leo Castle passed away in the hospital on April 15, 2025. He was born in Madison, WI to Leonard William and Josepha Laura (Patterson) Castle on February 26, 1939. As a teenager he worked for his dad at Taylor’s Deep Rock Gas station. He attended Madison Central High School and MATC.

He joined the Navy, served on the submarine the Clamagore. After being honorably discharged he returned to Madison and worked as a bartender. He and his wife Janet bought Bob and Gene’s on University Avenue which they ran for 18 years until it was demolished for student housing. Leo and Jan then bought the Village Bar on Madison’s west side. They ran that for 22 years until their retirement.

Leo was a great storyteller regaling friends and family with funny incidents that had happened to him and Janet or other people he knew. The stories were amusing but never cruel. It was suggested he should write a book.

He was preceded in death by his parents, brother Patrick, his many sisters-in-law and brothers-in-law.

He is survived by the love of his life his wife of 63 years, Janet, his brother Michael, his sisters Mary Anne Sobek, and Sally and her husband Glen Lee.

Leo was loved, admired and the rock of the family. His passing leaves a hole in the heart of many. The world is a dimmer place without him.

There will be a visitation on Tuesday, April 29 at Cress Funeral Home, 3610 Speedway Road, from 12 pm until the time of the funeral service at 1 pm. In lieu of flowers, memorials in Leo’s name may be made to the Wounded Warriors  (https://www.woundedwarriorproject.org/donate  ).

The family would like to thank the staff at the VA for their wonderful compassion and care.