Tuesday, May 26, 2026

Jeopardy Season 42 Update: Characters Welcome

 

 

As I've mentioned more than once in my articles about Jeopardy not long before Alex Trebek passed away I was attempting to write on the 100 greatest champions in history. By the time we were two full years into the post-Trebek era the book was on hiatus and will probably never be published which, if I'm being honest, probably is the best thing for it.

Looking back on it years later one of the biggest issues was that the writing was very much that of an encyclopedia with little to interest someone who wasn't a Jeopardy fan. Part of it may have been because this was the most impersonal set of non-fiction writing I've done with almost none of my love of the show in it. However in recent years I've begun to think they may not have been my only problem.

I'd watched Jeopardy for more than a quarter of a century before I began to write the book on the subject. When I was writing it I mostly focused on the details of how each champion played the game, how they did on Daily Doubles, etc. Part of it was that my personality wasn't there but another problem was there wasn't a lot of the contestants personality. And that is at least partially my fault.

Jeopardy is an incredible show in large part because it was – and still is – perhaps the only game show where everybody takes themselves seriously. The contestants are the stars of the show and one of the things that makes them stars is just how intelligent they were and the breadth and depth of the knowledge they had. That's what makes it a great show.

What it doesn't necessarily lead to is the kind of personalities that lend itself to great writing. Jeopardy is a competition, mental rather than physical, but a competition and part of what makes a great competition is the personalities of the stars. And that's the one area where Jeopardy is lacking in comparison not just to television as a whole but other game shows. When you have to take the show seriously as you do Jeopardy there isn't a lot of room for antics or quirks. This was especially true when the show had a five game limit for champions – a week rarely gives anybody a chance to establish themselves as an individual on a TV show – and it really didn't change much after the limit was removed. For all his incredible intellect and competitiveness Ken Jennings really didn't get a chance to show much in the way of a personality during his incredible 74 game run. In the many postseason tournaments that followed he would get a chance to do so, particularly as he played against many of his fellow competitors but not much at first.

The same has to be said for almost every great Jeopardy player for much of the Trebek era, even when it comes to winners of Tournaments of Champions. Chuck Forrest and Frank Spangenberg, to take two of the most prominent of the early champions were known for their achievements on Jeopardy rather than any thing they did while they were on the show as individuals. This was true for every major winner during the five game period. Ryan Holznagel and Mike Dupee were great Jeopardy players but besides having their Tournament of Champions won in 1995 and 1996 I really couldn't tell you of any single distinctive personality trait. Gameplay is one thing, character is another.

This was true for pretty much the next fourteen years. And honestly it wasn't a flaw but something I think most viewers would respect. Indeed I'd argue its not a bug in the machinery but a sign Jeopardy is working perfectly. Everyone who has appeared on Jeopardy comes from every walk of life.  They're not actors or reality show stars; they're the average person. They're lawyers, they're teachers, accountants, students, writers, engineers, scientists, and while there are some actors, they're usually ones who didn't get their big break. The only role you're being asked to play is a game show contestant. You become a celebrity if you do well on Jeopardy, not the other way around for most entertainment.

And that's the main reason why, even though there are some fan sites devoted to Jeopardy, I only occasionally visit them and anytime someone rags on a contestant for having a personality they don't like – or indeed no personality at all – I roll my eyes. They're trying to win money on a game show answering incredibly difficult questions. They're not there to win likes and the raves of the online masses. My only qualification for a great Jeopardy champion is the number of wins and the amount of money they win. End of discussion. Likability doesn't enter to it.

That was true, by and large, of almost every super-champion while Alex Trebek was hosting. Oh, occasionally there'd be some with formidable personalities such as James Holzhauer and Austin Rogers but those were exceptions rather than the rule. I never understood what made so many people repulsed by Arthur Chu during his eleven game run or why Matt Jackson was considered so dynamic by fans. I admired them both for their incredible gameplay and I asked for little more.

I'm not sure when exactly that began to change. I don't think it began as much with the first wave of super-champions but the first Jeopardy Masters. Having four of the winningest Jeopardy players all of time sharing the stage with the winningest one in history really helped bring it out. James Holzhauer embracing the label 'self-described game show villain', Amy Schneider joking to Ken was it was like to after 40 wins because she had no one to compare it too, Mattea Roach increasing relatability (particular in the aftermath of her father's death while the tournament was being recorded), Matt Amodio's increasing wistfulness, Andrew He's charm and the utter joy that was Sam Buttrey helped make me and I suspect a generation of viewers really relate to Jeopardy champions in a way we hadn't in the decade past. That has played out in every Masters that has followed – and why I can only wait for whenever the 2026 one happens. (It's not on the summer schedule though producers say it will happen.)

While several players in Season 39 had intriguing personalities such as Ray LaLonde and Troy Meyer that combined with the endless postseason of Season 40 made it hard for them to stand out. Then in the aftermath we've been getting more great Jeopardy players who also have fascinating personalities.

We saw it with Drew Basile, who had the added advantage of having been on Survivor and Isaac Hirsch with his ridiculous suits and wonderful cheeriness, both of which were really on display in last year's Masters. There was a bit more last year from Liam Starnes being the first Jeopardy champion to be born during Ken Jennings run (which made everyone, not just Ken feel old) Kevin Laskowski a priest who seemed to know more about rap then the Bible and the lovable Drew Goins who became a fan favorite even as he earned a Second Chance (and a third)

 And then almost from the start of Season 42 it's been like great Jeopardy champions have suddenly become fascinating characters to go with them. We saw this play out in the final weeks of eligibility before the 2026 postseason began when Paolo Pasco, a crossword puzzle designer managed to win seven games in the opening weeks of the season. He was then defeated by Steven Olson, a band director who was just as much fun to watch as he was to play. Then TJ Fisher, an overly cheerful champion, lucked into 5 wins which would get him into the Tournament of Champions.

By the time the eligibility period was over we were greeted by another super-champion the extremely likable Harrison Whitaker, who won 14 games and $373,999. And ever since the postseason ended it seems like we've been getting the kinds of storylines that, if they took place in a soap opera, you wouldn't believe them.

Here's Jamie Ding, who wanted to describe himself as a faceless bureaucrat in his introduction, a man who as a boy had attended the National Geographic Bee that Alex Trebek had hosted. He went on to just win and win until he finished in fifth place in both money won and games won. The fact that's he also a child of immigrants and a person of color has led him to be the kind of person that Jeopardy as much as the world needs right now.

And how was he finally defeated? The man who won 24 runaway games lost in a runaway to chess player Greg Shahade. He won just 3 games and $74,602 but Jeopardy fans know that was more then enough for Emma Boettcher, the play who ended James Holzhauer's streak back in 2019, to be invited back to that year's TOC. That he isn't listed as qualified yet is a formality at this point.

Then less than two weeks after Jamie's run ended another super-champion arrived Tristan Williams. Tristan, who the internet compared to Woody in the Toy Story franchise made a different kind of history when he became the first player to win exactly 10 games. It's remarkable when you think about that in the 22 seasons since the five game limit was removed we've had 9 game winners and eleven game winners but no one who won ten. That meant we had three super-champions this season.

But wait, it actually gets better. Tristan was defeated last Wednesday by Chris D'Angelo. Chris has spent so much of his life to trying to make it onto Jeopardy that his sister Jen turned into a TV movie for Hulu called Quiz Lady which would star Awkwafina playing her brother and I suppose Sandra Oh is Jen. This film went on to win the Emmy for Best TV Movie in 2024. And now two years after that Chris finally made it on Jeopardy and today has officially qualified for the next Tournament of Champions. Real life has duplicated fiction in the best possible way.

For all we know Chris may become a super-champion in his own right but there's already another great storyline for the 2027 Tournament of Champions. Not one but two super-champion killers are going to be participating in the Tournament of Champions. The three players who get byes into the semifinals have already won double digits in games for the first time since the process was founded in 2022. And who else will be participating in the next Tournament of Champions?

Why Ron Lalonde, the identical twin brother of super-champion Ray Lalonde. Shonda Rhimes wouldn't write this stuff!

Now to be clear we are very much male heavy for the next Tournament of Champions: as of this writing only seven players have qualified and all of them identify as male. That's unless you count the winner of this year's Celebrity Jeopardy Mina Kimes, a journalist who happens to be an analyst on ESPN. But that's an interesting storyline as well, considering that one of the participants is the inspiration for a TV show. And as I said in a previous article any celebrity whose willing to risk national embarrassment competing against so many great Jeopardy players is okay in my book.

It's never been a necessity for a Jeopardy champion to have a good personality to go along with their great gameplay for me and other viewers. I will say its added an additional layer of pleasure to watching that I didn't realize I was missing or even needed. Just to be clear all future Jeopardy players, it's still not a requirement in your competitive play. But we're all glad when it happens.

And Chris? Now Awkwafina's going to want to get pictures with you to make her look good.

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