I get why Dice brought Kenny, Dice was legitimately hated by large groups of people. Jimmy just saw him do it and assumed that's what big-shot comedians did, he doesn't seem to understand that Dice only did it because he was extremely divisive.

My theory:

Jimmy is an agoraphobe and has social anxiety. Kenny is there to talk to people so Jimmy doesn't have to. Jimmy is sensitive about this and attempts to save face by claiming Kenny is an assistant/bodyguard, even though the notion that a nobody like Jimmy needs either of those things is patently absurd.

His need for a chaperone isn't so much hateable as it is pitiful.

Nice title.

Kenny takes care of shit for Jimmy. He's more of an assistant and Jimmy finds it worth his money. Also it's like having a travel companion...which makes you realize Jimmy pays to have friends.