James Holzhauer Begins ‘Jeopardy! The Greatest of All Time’ Battle vs. Jennings, Rutter Tuesday Night

One of the most anticipated game show showdowns of all time will begin on Tuesday night, as sports bettor and poker player James Holzhauer faces off against Ken Jennings and Brad Rutter for Jeopardy supremacy in a contest that could span as many as seven nights.

Jeopardy James Holzhauer Jennings Rutter

James Holzhauer, Ken Jennings, and Brad Rutter (left to right) will face off starting Tuesday night to determine the greatest Jeopardy player of all time. (Image: ABC)

Booked as “Jeopardy! The Greatest of All Time,” the primetime contest pits the three most dominant players in the show’s history against each other for the first time. It’s a unique format that hasn’t been tried before, and we’re here to break it down for you ahead of the first night’s competition.

Meet the Contestants

The main reason this Jeopardy contest will be so popular in poker and gambling circles – other than the show’s incredible enduring popularity – is the presence of Holzhauer. The professional sports bettor also has a background in poker, and even teamed up with Partypoker to take part in the Partypoker Live Caribbean Poker Party, playing in the main event and (naturally) hosting a trivia night.

Holzhauer won 32 straight games in his main show run, then avenged his loss to Emma Boettcher in the Tournament of Champions final. That impressive result still left him short of the records set by Jennings, who won 75 straight games during his 2004 reign. Jennings also holds the record for the most money won in regular play, with $2.52 million, though Holzhauer’s big-money strategy brought him close, as he earned $2.46 million in a far shorter period of time.

Rutter may actually have the best resume of the three competitors. He only won five straight games during his initial run in 2000, but that’s because the rules at the time retired five-time champions. Since then, no human being has ever defeated him in play: he’s won nearly $4.7 million by coming out on top in various tournaments over the years, even betting Jennings head-to-head on multiple occasions.

The Format

This event will use a format similar to the finals of the Tournament of Champions. Each night, the contestants will play two back-to-back Jeopardy games. At the end of those two games, the player with the highest combined score will be declared the winner of that match.

To win the competition, a contestant must win three matches in total. That means that in the case of a three-way tie at two wins apiece, the Jeopardy GOAT might not be decided until a winner-takes-all Game 7, just like in many other sports.

Who’s Going to Win?

Sportsbooks aren’t taking any more money on the Jeopardy special, as the episodes have already been taped. When the contest was first announced, however, Bovada quickly put up odds, making Holzhauer (+110) and Jennings (+115) the virtual co-favorites over Rutter (+280).

Those odds were pounced on by sharps with Jeopardy knowledge, and Rutter soon became a +140 co-favorite with Holzhauer, with Jennings (+180) pushed slightly behind them.

With the odds moving so much, it might be worth looking at what some Jeopardy experts think.

I think many Jeopardy fans would love to see this event go the full seven matches, although I wouldn’t be surprised if one contestant goes on a run and sweeps three in a row,” ESPN producer James Quintong – a one-time Jeopardy champion – wrote Tuesday. “With that said, I’m going to predict Brad winning in six matches, with James taking two matches, and Ken capturing one match.”

If you prefer computer models, TheJeopardyFan.com has you covered. Their analysis predicts that the contest could go the way of any of the three contestants: Rutter is the slightest of favorites, winning just over 36.1 percent of the time in the site’s simulations, with Holzhauer (32.8 percent) and Jennings (31.1 percent) only fractionally behind.

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