Crossword clues for the word: KENJENNINGS The word KENJENNINGS has appeared as an answer to at least 4 crossword clues on different crossword puzzles. Crossword clues for KENJENNINGS Showing 1 to 4 of 4 results Clue(s) "Jeopardy!" co-host who holds the record for the longest winning streak in "Jeopardy!" history (74 wins) (2 wds.) 2004 "Jeopardy!" contestant who still holds the record for most money won in regular-season play ($2,520,700): 2 wds. Guy who won $2.5 million in 2004 Knowledgeable Juggernaut