In Jeopardy: Will James Holzhauer Surpass Jennings’ All-Time Records?

By in Entertainment on

James Holzhauer, a 34-year-old professional sports bettor from Las Vegas, is on pace to rewrite the Jeopardy history books in spectacular fashion as he’s shattering previous numbers and taking this illustrious gameshow to new heights. As of Friday, April 19th, Holzhauer has an 11-game winning streak, which isn’t as impressive as previous marks. But, his cash total and daily winnings have already broken records and it appears that there’s no end in sight to James Holzhauer’s amazing run on Jeopardy.

Entertainment betting sites have begun taking notice of Holzhauer’s performance as these online betting sites are now listing odds on James’ Jeopardy future. They’re also listing odds on whether or not Holzhauer can surpass the legendary Ken Jennings. Let’s take a look at these entertainment prop bets from BetOnline to see if we can find any value and make some money.

Will Holzhauer Break the All-Time Record of 74 Games?

  • Over 74.5 (+500)
  • Under 74.5 (-1000)

For those of you who do not know this, Ken Jennings is the “Babe Ruth” of Jeopardy as he set the mark for 74 wins in a row before losing on his 75th appearance. His remarkable run made him a celebrity and boosted the show’s ratings over 22% from the year before. He went on to publish two books and also landed in the Guinness Book of World’s Records. Jennings’ run seemed surreal at the time. And, looking back now, we can see just how impressive it was by comparing his win total to other previous champs. To put it in proper perspective, you would have to combine the next 5 contestants on the list of all-time winners to match what Jennings did.

The following is a list of the Top 10 Jeopardy contestants with the most wins:

  • 1. Ken Jennings 74 wins
  • 2. Julia Collins 20 wins
  • 3. Dave Madden 19 wins
  • 4. Matt Jackson 13 wins
  • 5. Austin Rogers 12 wins
  • 6. Seth Wilson 12 wins
  • 7. Arthur Chu 11 wins
  • 8. Jason Keller 9 wins
  • 9. Dan Pawson 9 wins
  • 10. Ben Ingram 8 wins

Breaking Jennings’ all-time win mark was unfathomable until Holzhauer came along. With that said, James still has a long way to go. As of this writing, he has 11 wins, which is good for 7th all-time. That total also makes him the 8th contestant ever to have double-digit wins on Jeopardy.

So, now we turn our attention to the first prop bet offered by BetOnline and that’s whether or not Holzhauer can break Jennings all-time record for wins. Oddsmakers don’t believe he will as they’ve set the odds pretty high against him at -1000 odds.

For this particular bet, I also have a hard time seeing James Holzhauer breaking this mark. For starters, only two people have ever won at least 20 games: Jennings and Collins who’s the winningest female contestant of all-time. Secondly, Holzhauer is very aggressive in his wagering and there’s a good chance that betting strategy will backfire on him somewhere down the line. And, with his gambling background, this is something that Holzhauer is definitely aware of.

Jeopardy Bet: Under 74.5 wins (-1000)

Can Holzhauer Surpass the All-Time Cash Winnings Mark?

Currently, betting odds for this record are off the board as of this writing. However, BetOnline had a prop bet that asked if Holzhauer would break Jennings’ all-time winnings for regular shows with Yes at +150 and No at -200.

During Jennings amazing 74 game win streak, he obliterated the record books for cash won. However, Jennings had an advantage over contestants before him. Up until 2003, contestants were done after winning 5 games. That rule changed by 2004 and Jennings took full advantage of it. With that said, Jennings holds the record for most money won during regular games (non-Tournaments) at $2.52 million. The following is a list of the top winners during regular play (numbers are best estimates based on different sources):

  • 1. Ken Jennings $2,520,700
  • 2. Dave Madden $432,400
  • 3. Julia Collins $429,100
  • 4. Matt Jackson $413,612
  • 5. Austin Rogers $413,000
  • 6. Arthur Chu $298,200
  • 7. Seth Wilson $265,002
  • 8. Tom Nissley $235,405
  • 9. Roger Craig $230,200
  • 10. Larissa Kelly $222,597

After 11 games, Holzhauer has won a total of $771,920 dollars. He quickly moved into 2nd place all-time for winnings and is on pace to surpass Jennings’ mark in roughly half the time it took Jennings to amass $2.5 million.

Brad Rutter holds the record for the most money ever won on Jeopardy at roughly $4.35 million dollars. This includes the handful of tournaments that he’s competed in. If you include Jennings’ tournament play, has a grand total of $3.27 million and is second all time. The following is a list of the all-time total winnings, which is the combination of regular play and tournament play:

  • 1. Brad Rutter: $4,385,702
  • 2. Ken Jennings: $3,270,700
  • 3. James Holzhauer: $771,920
  • 4. Roger Craig: $530,200
  • 5. Matt Jackson: $511,612
  • 6. Jerome Vered: $499,102
  • 7. Julia Collins: $478,100
  • 8. David Madden: $432,400
  • 9. Ben Ingram: $426,534
  • 10. Dan Pawson: $420,902

I believe Holzhauer actually has a chance at breaking Jennings’ regular play mark based on how aggressive he is and his incredible 11-day total. However, catching Rutter’s career total seems unlikely. As for Jennings, he had some advice for the younger Holzhauer:

“I’d give James the same advice I give everybody on ‘Jeopardy!’. Don’t wear a sweater. You’ll look like a dork.”

Will Holzhauer Break His Own One-Day Record?

  • Yes (-300)
  • No (+200)

On September 19th, 2010, Roger Craig set the all-time single-game record for most money won with $77,000 dollars. On April 9th, 2019, Holzhauer obliterated that mark with a one-day total of $110,914 dollars. That total was a goal that Holzhauer had set after he found out he would be on Jeopardy. The number is his daughter’s birthday.

As for the former record holder Craig, he made the following comments about Holzhauer’s record-breaking performance:

“This was so much fun to watch, congratulations to James for obliterating the old record! Those bets were fire and I can only hope there are many more in store for us…”

Craig has been credited by former champs as being a very gracious winner. It’s also something that Holzhauer recently acknowledged as well. James had stated that Craig did reach out to congratulate him on breaking the single-day record. He also stated that Craig helped prepare him for the media frenzy that was going to come his way.

A prop bet was released asking if he would break that mark. Before bettors could really take advantage of that wager opportunity, Holzhauer broke his mark with a total of $131,127 in his 10th appearance on the show. In total, Holzhauer holds the Top 4 single-day totals as of April 18th:

  • 1. $131,127 – James Holzhauer
  • 2. $110,914 – James Holzhauer
  • 3. $106,181 – James Holzhauer
  • 4. $89,158 – James Holzhauer
  • 5. $77,000 – Roger Craig

It’s unclear if BetOnline will keep these current odds for this prop bet. If they do then I’m going with “No” (+200). If they adjust these betting odds based on his $131,127 mark then it could offer some betting value based on what they list the “Yes” option at.

Will We Ever See Holzhauer take on Ken Jennings?

  • Yes (+110)
  • No (-150)

I believe this will be “Yes” due to Jeopardy’s pension for bringing back former champions to play in various tournaments. For example, Jeopardy held their Ultimate Tournament of Champions which saw Ken Jennings return. However, he was defeated by Brad Rutter in the finals of that tournament.

There’s no doubt that Holzhauer has boosted ratings and brought casual fans back. Furthermore, his exciting playing style will definitely endear him to the fans as they will undoubtedly want him to take on past champs like Jennings and Rutter.

As for Jennings, he’s been watching Holzhauer and made the following comments about James’ impressive performance:

Jeopardy Bet: Yes +110

Who Would Win Between Holzhauer and Jennings?

  • James Holzhauer (-200)
  • Ken Jennings (+150)

In the tweet above, Jennings shared his excitement. But, when it came to a potential head-to-head matchup with betting odds, Jennings wasn’t as enthusiastic:

“This seems like a weird marketplace given the fact that these games taped months ago and hundreds of people know the outcome.”

When looking at these betting odds, I believe there is plenty of value with Jennings’ line of +150. He’s set marks that will probably never be broken and the fact that he’s such a significant underdog is rather crazy. I understand the Holzhauer hype, but these odds are too much in favor of Holzhauer.

In regards to intelligence, I believe Jennings has the advantage. However, Holzhauer has the advantage with his aggressive betting. Either that will give him the edge over Jennings or that will lead to his crash and burn. Ken commented on Holzhauer’s approach to the game:

“He’s thinking about the game in a whole different way, and I never would’ve had the stomach to make some of those bets he’s making.”

Holzhauer stated that he was honored to be compared to previous champs like Jennings. He also gave some insight on the differences between Jennings and himself:

“I play the game very differently than Ken does. If you look at his statistics, he was a much more dominant player on the buzzer than I could ever hope to be. So I needed to play the game differently than he does to achieve the same results, if that makes sense. I created my approach to the game by myself, but I definitely see some similarities between me and champions who have come in the past. It’s a credit to them that they had this stuff figured out before I did.”

For this bet, I really like the value with Ken Jennings and I’m going with the all-time winner to defeat Holzhauer. I would love to see the betting odds with the addition of Brad Rutter to this mix.

Jeopardy Bet: Ken Jennings (+150)

Final Jeopardy: What is Amazing!

As of this week, Jeopardy wrapped up the tapings for their 35th season. The beloved host, 78-year-old Alex Trebek, vowed to be back for the show’s 36th season in September. If you recall, Trebek announced last month that he has Stage 4 Pancreatic cancer. He’s been open and honest with his fans all along and never shied away from his battle. Trebek says he’s feeling good right now and is excited about what Holzhauer is doing.

As for the man himself, Holzhauer is becoming a household name. He credits his success to luck and his background in sports betting. From there, James came up with an aggressive approach to the game that has dominated his opponents:

“I didn’t model my strategy after anyone in particular. My basic thoughts going in were, Okay, I want to have some money before Daily Doubles, and if this helps take my opponents off [their] game, that’s just a bonus. Some players in the past have said they bounced from category to category on purpose to throw everyone. I wasn’t trying to do that at all, it wasn’t my goal. I was just trying to get as much money I could before the big bets came in to leverage that. I do feel maybe the opponents I faced tried to play “the James style” — I guess you can call it that — of going for the high-value clues first, like what I was doing. But maybe since they didn’t go in with that game plan, they were less comfortable with that. That gave me a home-court advantage, so to speak.”

Holzhauer is definitely a wrecking machine on Jeopardy. But, like all good things, there will be an end to his run at some point. With that in mind, the question is whether or not his run will break the all-time mark set by Ken Jennings.

I clearly remember Jennings taking over pop culture during his 75 game run, which saw him win 74 straight shows. Holzhauer has the same feel that Jennings did. It’s an aura of invincibility. It’s also the debate of whether or not he’s a human or a cyborg. However, until he loses, Jeopardy fans will be on an exciting ride as we watch Holzhauer climb up the record books and shatter previous marks. Even with only 11 wins under his belt, Holzhauer has been nothing short of amazing.

Rick Rockwell

As a longtime freelance writer, avid sports fan, former athlete, and experienced sports bettor, Rick Rockwell has risen up the ranks at to become the self-professed "King of the Blog" in his first year with the site. ...

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