The answer to the crossword for the term 'WINNER IN A 1948 HEADLINE' is 'DEWEY', a five letter word. Thomas E. Dewey was the Republican candidate in the 1948 United States presidential election, and his victory was widely predicted by the media. However, he ultimately lost to incumbent President Harry S. Truman. The famous headline 'Dewey Defeats Truman' was printed in the Chicago Tribune on November 3, 1948, the day after the election.