In 15 seasons with Pittsburgh, Friend pitched on five last-place teams and is the only pitcher to have lost more than 200 (230) while winning fewer than 200 (197). In 1955 he became the first to lead a major league in ERA (2.83) while pitching for a last-place team. Friend twice topped the NL in hits allowed, and lost a league-high 19 in both 1959 and 1961. But he paced the NL in starts each season from 1956 through 1958, innings in 1956 and 1957, and tied with Warren Spahn for the NL lead with 22 wins in 1958. Friend shares the NL record with two All-Star Game victories (1956 and 1960), and lost the 1958 All-Star Game as a reliever. Friend lost Games Two and Six in the dramatic 1960 Yankee-Pirate World Series. A Purdue graduate, Friend served as Pittsburgh and NL player representative.