Greatest Chicago Cubs Outfielders of All Time

If this were a career list instead of just a career-with-the-Cubs list, Dawson might be No. 2. The Hall of Famer played 21 Major League seasons, but just six came in Chicago. They were an impressive six, though. Impressive enough to make No. 4 here.

Dawson signed with the Cubs ahead of the 1986 season after spending 11 years in Montreal with the Expos. The NL didn’t have a designated hitter at the time and the grass of Wrigley Field ended up prolonging Dawson’s career as he was able to get off the glorified concrete in Montreal.

Dawson won NL MVP in his first season in Chicago by leading all of baseball with 49 home runs and 137 RBIs. He was named an All-Star in five of six years with the Cubs, and his .507 slugging mark ranks seventh in team history.

3. Hack Wilson (1926-1931)

Wilson didn’t look much like a big-leaguer in his first three years with the New York Giants, producing just a 2.1 WAR total over three summers. But once he joined the Cubs, he became one of the best players in the sport in the late 1920s.

Wilson joined the Cubs in 1926, his fourth year, and immediately led the NL in home runs and walks, earning a fifth-place finish in MVP voting.

He’d finish in the top 12 in NL MVP voting each of the next three seasons, too, before finally capturing the honor in 1930 with one of the greatest seasons ever: Wilson slashed .356/.454/.723 with 56 home runs, 191 RBIs, and 105 walks. That RBI total remains the highest single-season total in MLB history.

2. Billy Williams (1959-1974)

A Cubs legend, Williams remains one of the top two or three most beloved players in franchise history, having played 16 of his 18 years on the north side of Chicago.

Williams had just two superstar seasons, finishing second in MVP voting in both in 1970 and 1972. For his other 14 years in a Cubs uniform, he was merely really good. Williams ranks third in offensive WAR, games, hits, and home runs in Cubs history, and he earned MVP votes eight times from 1964 to 1973.

1. Sammy Sosa (1992-2004)

Sosa’s legacy with the Cubs is complicated. But in the late 1990s, "Slammin’ Sammy" was so famous that even your grandmother who didn’t watch baseball knew who he was.

Sosa became a regular with the Cubs in 1993 at age 24. But he became a superstar in 1998 when he hit 66 home runs en route to MVP honors. He would ultimately hit 40 or more home runs seven times and eclipse the 60-homer mark three times.

Performance-enhancing drug allegations came shortly after his rise to stardom and have haunted him since. Though he has never formally admitted to their usage, he apologized in 2024 while acknowledging that he "made mistakes."