Sammy Sosa: 36 SB in 1993, 34 SB in 1995
Mostly known for his ability to obliterate baseballs onto Waveland Avenue, Sammy Sosa was actually a fairly decent base-stealing threat throughout the 90s and he exceeded 30 stolen bases with the team twice. Sosa's speed started to fade around the same time he began slapping 60 home runs a year in the late 90s and early 2000s. But Sosa finished his career with 234 stolen bases, not too shabby.
Bob Dernier: 45 SB in 1984, 31 SB in 1985
Center fielder Bob Dernier spent four years on the North Side, adding 119 stolen bases to his career total (218). This came with back-to-back years where the former Philly standout surpassed 30 SB in 1984 and 1985. Although the Cubs were not good during this time, Dernier contributed to the 182 stolen bases to team collected in 1985, which was second in the league that year.
Ivan De Jesus: 41 SB in 1978, 44 SB in 1980
Ivan De Jesus was the starting shortstop for the Cubs for five seasons, where he put up great numbers. His best season came in 1978, where he led the league in runs scored (104) and set a career highs in walks (74). De Jesus used his ability to get on base to swipe a lot of bases, and he collected 154 as a Cub.