[13] Raines was caught stealing for the first time in 1981, after having begun his career with a then major league record 27 consecutive successful stolen bases.

Raines was the runner-up for the National League's Rookie of the Year Award in 1981, which was won by Los Angeles Dodgers pitcher Fernando Valenzuela.

[14] To avoid leaving the drug in his locker, Raines carried it in his hip pocket, and slid headfirst when running the bases.

Raines became a free agent on November 12, 1986,[15] but in spite of his league-leading play no team made a serious attempt to sign him[18] (in a period when Major League Baseball owners colluded to keep salaries down).

[18] In his first game back, on May 2, facing the Mets, although Raines had not participated in spring training or any other competitive preparation for the season, he hit the first pitch he saw off the right-field wall for a triple.

Raines finished the game with four hits in five at-bats, three runs, one walk, a stolen base, and a game-winning grand slam in the 10th inning.

[22] The Expos traded Raines to the Chicago White Sox on December 20, 1990, along with Jeff Carter and a player to be named later (PTBNL), later identified as Mario Brito, in exchange for Iván Calderón and Barry Jones.

In 1993, despite missing nearly six weeks in April and May due to a torn ligament in his thumb he sustained while stealing a base, he managed to hit .306 with 16 home runs as the White Sox won the American League Western Division title.

[24] In the 1993 American League Championship Series against the Toronto Blue Jays, Raines posted a .444 batting average and scored five runs in a losing cause.

[25] On December 28, 1995, the White Sox traded Raines to the New York Yankees for future considerations; in February 1996, the teams agreed on Blaise Kozeniewski as the return.

After a kidney biopsy on July 23, Raines was diagnosed with lupus and spent the rest of the year undergoing treatment and recovery.

[15] At the Expos home opener in 2001, Raines received what he described as the longest and loudest standing ovation in his entire career, resulting in the pitcher walking him on four pitches.

Raines underwent surgery on May 31 due to a left shoulder strain, and spent time rehabilitating with the Expos Triple-A club, the Ottawa Lynx.

With 808 steals in his career, Raines has the fourth-highest total in major league history, behind Rickey Henderson, Lou Brock and Ty Cobb.

[38] Raines's career stolen base percentage (84.7%) was the highest in major league history for players with 300 or more attempts, until he was surpassed by Carlos Beltrán with an 86.4% success rate.

[citation needed] He is also listed as the 40th greatest non-pitcher in major-league history according to Bill James's win shares formula, one place ahead of Mark McGwire.

He won a Silver Slugger Award as an outfielder in 1986 when he led the National League in both batting average and on-base percentage.

[47][48][49][50][51] Raines began his coaching career in 2003 as manager of the Class A-Advanced Brevard County Manatees affiliate of the Expos.

After the 2010 season, the Bears moved to the Canadian American Association of Professional Baseball, and the team announced Raines would return to manage in 2011.

"[58] In 2007, he moved to Estrella Mountain Ranch, a suburb of Phoenix, Arizona, and married Shannon Watson from Arnprior, Ontario.

[60] In 2017, Raines published his autobiography, written with journalist Alan Maimon, Rock Solid: My Life in Baseball's Fast Lane.