Kennedy was the frontman and lead guitar of Wanderlust, the jam band that Roadie spent years working for, first as general crew, eventually working his way up to their trusted guitar tech. The band recently split up after many years, but it was an amicable parting of the ways, and they're still friends. Wanderlust had a big cult following, and they still have their loyal fans eagerly awaiting whatever its members do next, but for now, Kennedy's just enjoying some time off.
Kennedy originally founded the band with his then-future-wife Shea. They divorced eventually, but they're still friends, just not right for each other in that way. Roadie has known the members of the band since he was a teenager-- they're some of the longest-lasting relationships in his life. In some ways, he grew up around them. He and Kennedy still keep in touch, and whether he asks for it or not, Kennedy's eager to offer advice and support to his little baby roadie now that he's off to spread his wings.
Kennedy is friendly, kind, and canny, if a little bit a space cadet and very much a character. He never wears any shoes unless it's absolutely required, and never happily. Yes, he walks around New York City's streets completely barefoot-- when he's not using his unicycle to get around. He owns a pet iguana named Jeffrey, which often rides around on his shoulder. You could maybe say he's a hippie, but mostly he's just Kennedy.