Barfield had by far the best outfield arm of the 1980s. He led American League outfielders in assists three times (198587). Along with George Bell (LF) and Lloyd Moseby (CF), Barfield starred in what many analysts considered the best all-around outfield of the 1980s.

Selected by the Blue Jays in the ninth round of the 1977 amateur draft, Barfield debuted in the majors in 1981 and was a regular the following season. In 1985, he helped Toronto reach the playoffs for the first time. He also topped 20 home runs six times, became the first Blue Jay to hit a pinch grand slam (1982), and the first to hit 20 homers and steal 20 bases in the same season (1985).

Despite the Blue Jays' failure to defend their division title from the previous year, Barfield enjoyed his best personal season in 1986. He collected career-highs in batting average (.289), RBI (108), runs (107), hits (170) and doubles (35). He also hit a career-best 40 home runs, leading the major leagues and setting a team record which lasted one year. In addition, Barfield was awarded the Gold Glove Award and selected to the American League All-Star team. Barfield was traded to the Yankees for pitcher Al Leiter on April 30, 1989. He won his second Gold Glove in 1987, but his offensive numbers declined noticeably. He hit 25 home runs for New York in 1990, but never produced like the club had hoped. Injuries and general ineffectiveness forced his retirement in 1992, at age 32.

Barfield was a career .256 hitter with 241 home runs and 716 RBI in 1428 games. He was inducted in the Kinston Professional Baseball Hall of Fame in 1990.

In 2007 and 2008, Barfield served as a color commentator for Blue Jays games on CBC. Currently, Jesse Barfield works at Competitive Edge Sports in The Woodlands, Texas.

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