Stewart was somewhat typical of the Democratic Party's Southern wing of that era. He has been considered to be at least somewhat an ally of Memphis political boss E. H. Crump, but less so than Tennessee's other Senator of the time, Memphian Kenneth McKellar. Unlike some of the other Southern Senators, however, Stewart was also a staunch pro-Roosevelt New Dealer and was the only successful Senator to win a primary and purge an incumbent Senator whom Roosevelt targeted in the 1938 midterm election "purge." Stewart was reelected in 1942. In that year, shortly after the beginning of Japanese internment, he introduced a bill in the Senate to revoke citizenship from all American-born persons of Japanese ancestry. In 1948, he was challenged for renomination by Estes Kefauver, a progressive East Tennessean who defeated him. Edward J. Meeman, the influential editor of the "Memphis Press-Scimitar", supported Kefauver to undermine the Crump machine, with which Meeman had long been at odds. After he defeated Stewart, Kefauver then handily prevailed over the Republican nominee, B. Carroll Reece.