A native of Cleveland, Ohio, Frey never reached the major leagues as a player. A left-handed batting-and-throwing outfielder, Frey spent much of his career in the farm systems of the Boston/Milwaukee Braves and St. Louis Cardinals. A recurring arm injury prevented him from his best shot at the big leagues, in. Following the end of Frey's playing career in, he joined the Baltimore Orioles as a scout and MiLB manager. Frey was promoted to the MLB Orioles' coaching staff under Earl Weaver, in 1970, and coached on three AL pennant winners and one World Series champion through 1979.
A week after the end of the 1979 World Series on October 24, Frey was named to succeed Whitey Herzog as manager of the Kansas City Royals. He led the Royals to a 97–65 mark and the American League West Division title in 1980; then, in the 1980 American League Championship Series, the Royals swept their long-time postseason nemesis, the New York Yankees, in three straight games to capture the AL title. But Frey's Royals dropped the World Series to the Philadelphia Phillies, in six games. During the strike-marred 1981 season, in which the Royals finished the first half with a 20–30 record, Frey was criticized widely for not taking full advantage of a team built for speed and for failing to motivate his players by Kansas City vice president/general manager Joe Burke. Frey was relieved of his duties on August 31, despite the 10–10 ballclub leading the second-half American League West standings. His replacement was Dick Howser, who had lost his managerial job with the Yankees after the previous year's ALCS. Frey's record in just less than two seasons as Royals manager was 127–105.
Frey then returned to the coaching ranks with the New York Mets for 1982–83. He was hired by the Chicago Cubs for the 1984 season, and again struck paydirt as the Cubs won the division title, earning their first post-season appearance since 1945. During the clubhouse celebration following the division-clinching in Pittsburgh, Frey declared, "The monkey's off our back!" The Cubs won the first two games against the San Diego Padres in the National League Championship Series at Wrigley Field, before they went to San Diego needing to win just one of the next three games. The Cubs lost the next three games, and many critics blamed Frey for mishandling the pitching staff. Still, the 1984 Cubs are revered among Cubs fans. After a trying 1985 season in which the entire five-man starting rotation simultaneously spent time on the disabled list, the Cubs sputtered in 1986. Frey was fired two months into the season and replaced by John Vukovich. The next year, Frey surfaced as a color commentator on the Cubs' WGN Radio broadcasts. 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 pitcherLee Smith to Boston for journeymanpitchersAl 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 closerGoose 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. So Frey made a bold move in the winter of 1988, trading budding star Rafael Palmeiro and young pitcher Jamie Moyer to the Texas Rangers for a number of players, including Mitch Williams. The trade appeared to pay off for the Cubs with respect to the 1989 season as Williams saved 36 games, the Cubs won a division title and Moyer and Palmeiro struggled in Texas. But Williams had just one more forgettable year for the Cubs before being traded to Philadelphia in 1991, and Palmeiro and Moyer went on to have productive careers. Following the 1989 campaign, Frey was named co-Executive of the Year by United Press International. After a disappointing 1990 season, Frey was active on the free agent market, acquiring former Toronto Blue Jay and American League MVPGeorge Bell, former Cincinnati Redsstarting pitcherDanny Jackson, and former Houston Astros closer Dave Smith. Jackson and Smith flopped in their roles in 1991, and Zimmer was fired – apparently on orders from Tribune Co. CEODonald Grenesko, in May 1991. Jim Essian, a former journeyman catcher and Iowa Cubs manager, replaced Zimmer for the remainder of the season. Frey was reassigned within the organization after the 1991 season, replaced by former Chicago White Sox general manager Larry Himes.
