His real first name was Ransom, and gosh darnit, he was kind of handsome. (His teammates thought he looked like Gregory Peck). "Handsome Ransom" Jackson was one of the best players on the Cubs in the early 50s; a National League all-star third-baseman in 1954 and 1955. He hit 19, 19, and 21 homers in 1953-55 (his three seasons on the Cubs), and was a pretty good fielder too. (In 1955 he led NL third basemen in double plays.)

His greatest day in a Cubs uniform was April 17, 1954 against St. Louis. Jackson had four hits - including a home run that hit an apartment building on Waveland Avenue. With the wind blowing out at Wrigley Field, the Cubs beat the Cardinals 23–13 in a National League record (at the time) three hour and 43 minute game. The two teams combined for 35 hits — including five homers.

The Dodgers traded Walt Moryn, Don Hoak, and Russ Meyer to the Cubs for Jackson and pitcher Don Elston after the 1955 season with the expectation that the slugger would succeed Jackie Robinson at third base. Unfortunately for Jackson and the Dodgers, he suffered a serious knee injury in 1957, and Handsome Ransom never played regularly again.