Can Ken Jennings lose? The Jeopardy champ who has become Jeopardy's first million dollar winner may not be invincible after all. An unsubstantiated rumor on Jason Kottke’s website, www.kottke.org, states that Jennings has lost but that the game (his 75th) won’t air until late October. The Mormon phenom ends up taking home over two million dollars.