Gale Gilbert (NFL)
When: 1974, Red Bluff, Calif.
When he went pro: Gilbert developed a much more ignominious claim to fame than Drury: He is the only man to be a member of five consecutive teams that lost in the Super Bowl. A career backup quarterback, Gilbert’s football highlights started when he served as the Cal quarterback during the famous game against Stanford when his Bears won on a touchdown stampeding through the Stanford band, then played as Jim Kelly’s backup for the four Bills teams that lost in the Super Bowl, as well as the Chargers who fell to the 49ers the following year. Gilbert, whose son Garrett Gilbert is currently an NFL backup quarterback himself, also lost in the LLWS final.