In December 1987, the Tribune Co. hired Frey to replace his old boss, general manager Dallas Green, who had resigned two months earlier. Frey hired his lifelong friend, Zimmer, to manage the team, and immediately made his presence felt. Within weeks of his hiring, Frey dealt relief pitcher Lee Smith to Boston for journeyman pitchers Al Nipper and Calvin Schiraldi, the latter of whom was best known for playing a part in the Red Sox' 1986 World Series collapse. Frey also traded the popular Keith Moreland to San Diego for closer Goose Gossage, who had played a big part on the Padres team that eliminated the Cubs, four years earlier. Neither move worked, and the Cubs were without a closer.