He was named to the NL All-Star team in 1957, 1958, and 1960 while with the Cardinals, and allowed only two hits and no runs in 3+2⁄3 innings in the three appearances; the 1957 game was played at Sportsman's Park in St. Louis.

[4] After the 1962 season, Jackson was traded to the Cubs along with Lindy McDaniel in a six-player deal; the Cardinals received three players including Don Cardwell.

[6] In early 1966 he was traded to the Phillies in the deal which brought Ferguson Jenkins to Chicago, and he ended the season as one of six pitchers tied for the league shutout lead with five.

In 1967, he won his 171st game to pass Bill Doak, who had previously been the winningest NL right-hander of the 20th century to never play for a pennant winner.

He tied a record held by Claude Passeau by four times having the most total chances among pitchers with a perfect 1.000 fielding percentage (1957, 1964, 1965, 1968).

He ran for governor in 1978,[7][8] but was fourth in the six-man GOP primary in August, won by Allan Larsen,[9][10] who lost the general election to incumbent John Evans.