Raines begins career rebirth with White Sox

On Dec. 23, 1990, the Expos traded Raines and two prospects to the Chicago White Sox in exchange for Ivan Calderon and Barry Jones. The 31-year-old Raines was coming off his 10th full season in the big leagues where he posted a .287 batting average with a .379 on-base percentage, nine home runs, 62 RBI, 49 stolen bases and 70 walks. It was a typically outstanding season for Raines. In his 10 full seasons with Montreal, Raines averaged .302 at the plate with a .391 OBP, 10 home runs, 55 RBI, 63 steals and 77 walks. But Raines had been anxious to play for a contender as the Expos slowly entered rebuilding mode. “I’ll miss the fans, a lot of the good times and a little of the bad times, the friends and the relationships I had with the players and the city,” Raines told the Associated Press. “I think it’s probably the toughest thing I’ve ever had to do in my life – to leave the place that I practically grew up in.”

Raines was selected by the Expos in the fifth round of the 1977 MLB Draft, and by 1979 was in the big leagues. In 1981, Raines became a regular in the lineup and took the National League by storm – stealing a league-best 71 bases in 88 games over that strike-shortened season. The Expos advanced to the NLCS that year before losing to the Dodgers in five games.

Over the next decade, Raines won three more stolen base titles and the 1986 NL batting crown, but the Expos never again advanced to the postseason despite a lineup that also included future Hall of Famers Gary Carter and Andre Dawson. Recognized as one of the best leadoff hitters in the game, Raines was a hot commodity when the Expos made him available via trade following the 1990 season.

“My main concern was finding a leadoff man, and Tim Raines is one of the best,” said Ron Schueler, the White Sox’s general manager, who immediately signed Raines to a three-year, $10 million-plus contract following the trade. “He adds a whole new excitement to our team.”

The White Sox installed Raines at the top of their batting order, and – following a breakout season in 1990 where Chicago went from last place to second – the team began a push that culminated in winning the 1993 AL West title. Raines scored 102 runs in both 1991 and 1992, then hit .306 with 16 home runs in just 115 games in 1993.

Raines would play five seasons with the White Sox, departing after the 1995 campaign when Chicago traded him to the Yankees. With New York, Raines became a valuable part-time starter who helped the Yankees win World Series titles in 1996 and 1998.