Moe "Guns" Jackson was Robert Freeman's wingman and friend from World War II. He dies from an erectile dysfuncion but Granddad does not know until a few days later due to Riley failing to deliver the message. Granddad told a story of how he and Moe took down two German planes during the war. While flying, Moe and Robert run into German fighter pilots. Robert is focused on fighting while Moe is playing around. Moe decided to bet Robert (in the middle of the fight) 2 bucks that he saves him from being killed. After a bit of argument, Robert accepts the bet. Robert manages to succesfully shoot down one plane but does as much luck with the next. Moe mocked Granddad when he shot at one of the Germans and missed horribly. Moe gets very cocky and closes his eyes while shooting at the Germans, but he himself misses horribly and shoots Robert. The German gets a clear shot insight but is out of ammo. This forces him to retreat. When Moe opens his eyes he sees the German retreating, thinking that he was the cause, thus ending the fight. He then reminds Robert that he now owes him 2 bucks. He wanted Robert to deliver his eulogy because he thought that he was good at saying deep things.
Moe was a loud, self-absorbed, immature person. Based on his personality, it came as no surprise when Moe asked to have his funeral on a party boat. Many people from his war days were at his funeral. They gave credit to him for Robert's accomplishments (Moe even somehow had one of Granddad's medals). According Cookie Freeman, "everyone knew that Moe was an asshole".