Kit Cloudkicker must have had a hard life before meeting Baloo, and then once he met Baloo and the Higher for Hire crew, his life vastly improved and gradually got better. That's what makes Kit's character so appealing, he had a difficult life and been in the company of shady characters, yet despite all of that, he turned out a good kid, a loyal friend and hard worker. That's why we all love Kit Cloudkicker so much. He's like the Artful Dodger in a way, who gave up life on the streets and settled in with a surrogate family.