From 1927 through 1946, he played for the St. Louis Browns (1927–1932; 1938–1939), Chicago White Sox (1932–1934), Washington Senators (1934–1936), Detroit Tigers (1939–1940) and New York Giants (1946).

Kress spent 1937 with the Minneapolis Millers of the American Association, hitting .330 and leading the league shortstops in total chances.

He was reacquired by the Browns along with Bobo Newsom and Buster Mills from the Boston Red Sox, the Millers' parent club, for Joe Vosmik on December 3, 1937.

During his minor league days with the Toronto Maple Leafs, Kress played a nine-inning game at nine positions.

As a shortstop, Kress recorded a .944 fielding percentage, 1761 putouts, 2357 assists, 243 errors in 4361 chances, and 558 double plays.

In addition to the Saints, he managed minor league clubs the Sacramento Solons and Indios de Ciudad Juárez.