Moe "Mo' Guns" Jackson was Robert Freeman's wingman and friend from World War II. In their younger days, Robert caught Moe necking with a girl he liked and never forgave him. He dies from an erectile dysfunction but Granddad does not know until a few days later due to Riley failing to deliver the message. At first, Grandad was all but overjoyed that Moe was finally dead, but refused to attend the funeral. However, the promise of something of Moe's being left to him in the last will was enough to coax him to Chicago.