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Leyland's first job in the majors came with the Chicago White Sox, who had hired Tony LaRussa as manager in 1982. Leyland and LaRussa had met three years earlier while managing opposing teams in the American Association, and one of LaRussa's first moves was to ask Leyland to join the White Sox as third-base coach. Leyland brought an impressive minor-league resume to the big leagues, having won three Manager-of-the-Year awards in eleven minor-league seasons since 1971, when at age 26 he ended an unremarkable career as a catcher in the Tigers' system to manage Detroit's Rookie League affiliate in Bristol for $6,000 a year.
Except for a short stint filling in for LaRussa during a suspension in 1985, Leyland had no major league managing experience when he was named manager of the Pirates in November by new Pirates GM Syd Thrift. But although the Pirates -- perpetual NL East doormats before Leyland's arrival -- again finished last with a 64-98 record in 1986, young stars Bobby Bonilla and Barry Bonds, along with starter Doug Drabek emerged to form a nucleus that had the Pirates in second place by 1988. After taking a step back in 1989, Leyland's 1990 squad (his favorite, by his own account) won 95 games and the division title, as Bonds won the MVP and Drabek the Cy Young.
But the team fell to Lou Piniella's Reds in the playoffs, starting a pattern of post-season futility that would continue for the next two years. In 1991 and 1992, despite winning 98 and 96 games respectively (in '92, after losing Bonilla to the Mets and 20-game winner John Smiley to the Reds, both via free agency) the Pirates lost to the Braves in the League Championship Series. In fairness to Leyland, the '91 and '92 series were both close contests and the team was hurt both times by Barry Bonds' inability to produce in the clutch. In 68 LCS at-bats, Bonds hit only .191 with 3 RBIs.
Pirates fans continued to cheer their team's skipper, even after three straight playoff disappointments and a slide back into mediocrity starting with a fifth-place finish in 1993 and continuing for another three losing seasons. Throughout his career in Pittsburgh, Leyland - a true Steel City folk hero -- consistently won the most applause of anyone in a Pirates uniform during pre-game introductions. An unusually intense competitor, Leyland was once described by longtime coach Rich Donnelly as being able to "make coffee nervous."
Ironically, Leyland finally found post-season success after leaving Pittsburgh in October 1996 for Florida. Under Leyland, the expensive Marlins team (featuring Bonilla at third base) finished second in the NL East but won their first playoff series against San Francisco (featuring Barry Bonds in left) and surprised Atlanta in the LCS before outdueling the Indians for the championship. After Craig Counsell scored the winning run for the Marlins against Cleveland's Jose Mesa in the seventh game of the World Series, Leyland charged around Miami's Pro Player Stadium yelling, "never give up!" with his index finger raised in triumph. Taking his own advice, Leyland returned to the helm in 1998, even though team owner GM Wayne Huizenga got rid of most of the Marlins' best players, trying to cut enough payroll to sell the team.
Leyland used an escape clause in his contract to defect to Colorado after his decimated defending champions lost 108 games in 1998. But after an unsatisfying season with the disappointing Rockies the veteran skipper called it quits, walking away from $4.5 million of a three-year, $6 million deal, the largest ever signed by a major-league manager. "I've been in clubhouses for 35 years," Leyland told the Rocky Mountain News. "I'd like to be home once in a while." Later, he admitted, "I don't have the energy to do it anymore" and vowed never to manage professionally again.