Elberfeld signed Jackson to his first professional contract, and recommended him to John McGraw, manager of the Giants.

[2][3] Jackson attended Ouachita Baptist University in Arkadelphia, Arkansas, where he starred on the college baseball team.

With Dave Bancroft and Heinie Groh, the Giants' starting shortstop and third baseman respectively, sidelined with injuries incurred during the 1923 season, Jackson drew notice as a fill-in.

The Giants lost the 1924 World Series to the Washington Senators, with Jackson committing a key error in Game 7.

[18] Though Jackson fell behind Blondy Ryan on the team's depth chart during the season,[20] he returned in the 1933 World Series, which the Giants won over the Senators.

[21] Terry stayed with Jackson as the Giants' starting shortstop for the 1934 season,[1] in which he drove in 101 runs and was chosen to appear in the 1934 MLB All-Star Game.

[22] Jackson played third base in his final two seasons,[23] serving as team captain,[21] although he struggled in the 1936 World Series,[24] which the Giants lost to the New York Yankees.

[4] Jackson signed a three-year contract with the Jersey City Giants of the Class-AA International League after the 1936 season.

[27][28] Jackson's knees prevented him from appearing in many games with Jersey City as a player,[2] but he remained as the team's manager until July 1938, when he was replaced with Hank DeBerry.

The Giants brought Jackson back to the majors as a coach for the remaining 18 months on his contract, succeeding Tommy Clarke, who became a scout.

[4] As defensive standouts have historically been overshadowed by power hitters in Baseball Hall of Fame voting, Jackson was not elected through the annual balloting process despite his record and achievements.