The crossword solution for the term TWO-TIME LOSER TO MCKINLEY is BRYAN, which is a 5 letter word. The answer refers to William Jennings BRYAN, an American politician who ran for President of the United States three times, losing twice to William McKinley in 1896 and 1900. BRYAN was a prominent leader of the Populist movement and a major figure in the Democratic Party during the late 19th and early 20th centuries.