Why it matters: "Jeopardy!" has held many mega-tournaments during its 36 years on the air, but starting tonight, it's aiming to find its greatest player of all time. The three contestants are Ken Jennings, who won 74 consecutive games; Brad Rutter, who's won the most money of any contestant; and James Holzhauer, who dominated this past "Jeopardy!" season and won its Tournament of Champions. Personally, I think James will win, given that he's the youngest and has played the most recently. However, Brad has beaten Ken in almost all their previous matchups (a notable exception is the 2011 tournament that was won by IBM's Watson computer), so maybe he'll come through again this time. Above all, I hope the competition is fun for host Alex Trebek as he thinks about the end of his tenure. -- Cathy (the WYWW "Jeopardy!" expert)