On Oct. 5, Guernsey's of New York will auction off some of the late country legend's goodies.
Muhammad Ali's ring robe
"Waylon and Muhammad were really good friends," says Guernsey's president Arlan Ettinger. The boxing icon gave Jennings this ring robe after his 1978 fight with Leon Spinks.
Estimated price: $20,000 to $30,000
Buddy Holly's 1958 Ariel Cyclone
Jennings, a close pal of Holly and a member of his post-Crickets band, was supposed to be on the ill-fated 1959 flight that took Holly's life.
Starting bid: $300,000