Crossword clues for the word: JACKDEMPSEY The word JACKDEMPSEY has appeared as an answer to at least 7 crossword clues on different crossword puzzles. Crossword clues for JACKDEMPSEY Showing 1 to 7 of 7 results Clue(s) '20s heavyweight champ "Boxer mentioned by the Notorious B.I.G. in ""Freestyle""" "Subject of this puzzle, born 6/24/1895" Boxing great born 6-24-1895 Boxing great who won his first world heavyweight title by defeating champion Jess Willard on July 4, 1919 (2 wds.) First athlete to appear on the cover of Time magazine Winner of the FIRST heavyweight title bout heard on radio