Tommy wasn't a mob minded guy like Oliver nor even a sad alpha like Morty. He was the kind of guy who got sleepy after a lot of drinking wine.
Tommy was married only once, to grumpy half-Armenian housemaid Nelly Kevorkian Hopper, in 1931. He and Nelly birthed a boy named Jockey in 1934 and a trio of triplets named the SZYSLAK sisters in 1946. The sisters were Mindy, Ellis and Holly.
He wasn't a great beer maker but he helped his nephew Moe relaunch Scorpio's for the baby boomer era as Moe's! He died in 1977.
The triplets mostly remain single while Jockey married a former go-go dancer named Molly Selma Thompson, Celia's older sister. They then birthed an only child named Joe Thompson Szyslak of Shelbyville, in 1969. He and Molly remain good friends, even after they divorced in 1984.