I once tried to write a long book of
the 100 greatest Jeopardy players of all time for many reasons but at the core
was a simple one: I was never convinced even after Ken Jennings incredible run
that he was the greatest Jeopardy player of all time.
Part of this was naturally due to the
rule change. Jennings came on to the scene in Season 20 the year that Jeopardy
lifted the five game limit for Jeopardy champions that had been present
since the show debuted in 1984 and went back to the original program. As Alex
Trebek himself once argued prior to the Ultimate Tournament of Champions: is it
possible that had any of the other players prior to Jennings played with no
limits they would have gone on as long as him or been better than him?
The former question will never be
answered satisfactorily and honestly the UTC didn't really answer that question
either. It proved one thing: Brad Rutter, the first playing to win a million
dollars in a tournament, was a better player then Ken Jennings and that would
be a constant on Jeopardy for the next fifteen years through the Battle of the
Decades and the Jeopardy All-Star Games. It wasn't until the Greatest of All
Time Tournament took place in January of 2020 that Jennings finally defeated
Brad (and James Holzhauer who we'll get to) and after that he immediately
retired from active play.
If we use the transitive property of
Jeopardy tournaments, arguing that if Jennings beat other Jeopardy champions in
a special tournament he was de facto their superior, we get an answer of sorts.
Jennings was able to beat Jerome Vered out for second place in the UTC Finals
but since he only played against him and Brad in that tournament that didn't
prove much. Jennings was able to beat five other Tournament of Champions
winners to get to the finals of the Battle of the Decades and they were pretty
good ones:
Michael Falk, 2006 Tournament of
Champions
Rachael Schwartz, 1994 Tournament of
Champions
Tom Cubbage, 1989 Tournament of
Champions
Russ Schumacher, 2004 Tournament of
Champions
Chuck Forrest, 1986 Tournament of
Champions
Of those five only Chuck gave him a
hell of a scare in the semi-finals, in what was the only non-runaway victory he
had during the semi-finals. When he got to the finals he was up against Brad
and Roger Craig, who among other things had broken Ken's one-day record of
$75,000 in his run. There were times in the finals where Roger had both Brad
and Ken where he wanted them but in both cases going all in on a Daily Double
beat him and he ended up losing to both.
The Jeopardy All-Star Games didn't
give a conclusive answer. Ken did do better than Austin Rogers in the Jeopardy
round of one game and Double Jeopardy round of another one and was considerably
better than Ben Ingram and Julia Collins in both of those games as well. Beyond that we can't really extend his ability
as being better then many of the other players in that tournament very well
because he was part of a team. In the finals he went up against Brad Rutter and
Pam Mueller in the Jeopardy round of Game 1 and the Double Jeopardy round of
Game 2. In Game 1 he actually was better than Brad for once but Team Brad ended
up ahead of his team by the end of Game 1 and in Game 2 Brad annihilated Ken
allowing himself a runaway. Pam Mueller, who is also an impressive Jeopardy
player in her own right, was trounced on both occasions.
Brad was for nearly 20 years the only
player in Jeopardy history who never lost a game (to a human). That streak
wasn't continuous the same way Ken or any other super champion and essentially
amounted to 29 consecutive victories over 19 years. It was always enough for me
to consider Brad the greatest Jeopardy player of all time mainly because it led
to him being the biggest money winner in Jeopardy history, a figure he still
maintains to this day. If we exclude his defeats in both the GOAT and the 2025
Masters Tournament Brad won just over $4.5 million dollars going up against
human competition.
And it's not like the players he was
up against were exactly pikers. None of them may have been the caliber of
Holzhauer or Schneider or even Matt Jackson or David Madden but by the time he
got to the GOAT he'd beaten no less than seven other TOC winners to that
point in addition to Roger Craig:
Million Dollar Masters
Bob Verini: 1987 Tournament of
Champions
Battle of The Decades
Mike Dupee: 1996 Tournament of
Champions
Mark Lowenthal: 1988 Tournament of
Champions
Dan Pawson: 2009 Tournament of
Champions
Leszek Pawlowicz: 1992 Tournament of
Champions
Tom Cubbage: 1989 Tournament of
Champions
Jeopardy All-Star Games
Colby Burnett: 2013 Tournament of
Champions
His undefeated streak is actually more
impressive because in two of these games he went into Final Jeopardy in a
distant third and still managed to win. In the second of these in the Jeopardy
All-Star Games both Pam Mueller and Alex Jacob humiliated him in the Double
Jeopardy round of the Jeopardy All-Star Games.
Alex Jacob won the 2015 Tournament of
Champions in dominant fashion and was superb against Brad in the Jeopardy round
of Game 1 until Brad found the Daily Double very late in that round to take the
lead. Both Alex Jacob and Roger Craig
had the better of Brad for much of their appearances on Jeopardy and the two of
them are considered by their peers as among the most dominant players of all
time despite each only winning six games in their original runs. In both cases
Brad knew he was lucky to get past them and win.
It was for that reason I always
considered Brad a better player then Ken. That being said I was always
impressed by many of the players who reached double digits in the last six
years of the post Trebek era. But I'm not sure I would ever have considered
them at Ken's level even given their prowess in short runs. For one let's look
at those players who reached 11 or more wins just for comparison with Ken.
Ken Jennings: $376,158
David Madden: $269,101
Arthur Chu: $297,200
Julia Collins: $231,310
Matt Jackson: $339, 411
Seth Wilson: $245,002
Austin Rogers: $394,700
Jason Zuffranieri: $332,243
Yes I left James Holzhauer's total out
of the discussion in this case. I'll get to it below.
With the exception of Austin Ken was a
better player than everyone else at this point in their run and as I mentioned
Ken trounced Austin the Jeopardy All-Star Games and did the same to Julia
Collins. Seth Wilson was on Julia's team along with Ben Ingram but Ken never
played against him in competition. I suspect he knew what he was doing when he
made Matt Jackson his first draft choice when picking his team and while Brad
would chose David for his team, the two never competed. Arthur and Jason never
got a chance to go against him, to the regret of millions like me who would
have loved to see the two face off.
Of course as the GOAT played out Ken
managed to beat James three times out of four while James beat Ken once. I do
wish he'd stop ducking a rematch – and no autocorrect was involved there.
(Jeopardy Masters humor.)
It's far tougher to make the argument
Brad was better than any of these super-champions because he never faced off
against any of them in the All-Star Games: for better or worse all of the
double digit players in that tournament only ended up in competition with Ken
Jennings or as part of his team or Brad's.
And considering how thoroughly James Holzhauer trounced Brad in the GOAT
tournament there's no question that Holzhauer is by far better than Brad as
well. Would Brad have done well had he faced off against so many of those
super-champions? We may never know.
This brings me to the players in the
post-Trebek era where the super-champions have come at a frankly ridiculous
rate and because of that we may want to use bigger numbers. During the first
fourteen years after Ken's run ended only one players Julia Collins, managed to
win 20 games, which was the second place total for five years. Since 2019 six
players have won 21 games or more including the reigning super-champion Jamie
Ding. For that reason its worth looking at
Ken in comparison to the five players on the Leaderboard of Legends who
are now directly below him with that many wins and see where they were at 21
because the results will surprise you. They certainly surprised me and I'm
supposedly an expert.
Jamie Ding: $609,000
Cris Panullo: $748,286
Mattea Roach: $506,584
Amy Schneider: $806,000
Matt Amodio: $740,001
James Holzhauer: $1,608,627
Ken Jennings: $697,760
I first noticed just how much Ken was
lagging behind so many of the all-time greats when I wrote about Cris Panullo
nearly four years ago. That was a celebration of Panullo's greatness but I
didn't think to compare it to Jennings. Now's the time to do just that.
That means looking at their track
record when it comes to runaway victories to that same point in their run:
Mattea Roach: 16
Ken Jennings: 16
Cris Panullo: 17
James Holzhauer: 19
Matt Amodio: 17
Amy Schneider: 19
Combining these two factors
increasingly makes it difficult to argue that Ken Jennings was better than any
of the five people directly behind him in wins. So now let's ask the million
dollar question (chump change to four of the players on this list, I know): are
these five super-champions better than Ken Jennings?
Let's go one by one.
With Cris Panullo its clear he was
more dominant a player in his original appearance both in terms of money won
and runaway victories. The reason I can't speak with any real confidence is
that Cris's postseason record is very short, having been humiliated in the 2024
Tournament of Champions.
With Mattea Roach, in terms of money
won Ken is far better than them and dead even in terms of runaways. However we
do have to consider the critical factor of their postseason record which is
considerable. Roach won the exhibition match of the 2022 Tournament of
Champions against Amy Schneider and Matt Amodio. And in the inaugural Jeopardy
Masters Tournament they more then held their own. Mattea beat Amy twice and
Matt once managed to get into the semi-finals of the Jeopardy Masters and while
they never defeated Holzhauer they came this close to doing so in the final
something Holzhauer acknowledged. Given their track record against so many
players who were superior to them on paper, it doesn't take much conjecture to
argue Mattea Roach could do just as well against Ken.
As for Jamie Ding who completed his
run in fifth place in both games and money won we'll have to wait until the
Tournament of Champions to see how it plays out. However considering that in
his 31 games Jamie didn't even come close to a million dollars – a figure that
Ken reached on his 30th game – I'm inclined to ran Ken ahead of him
at the present moment
If, when it comes to Mattea and Cris I
can't speak with certainty and Jamie has yet to prove himself, then with the three players directly behind Ken in
wins there is absolutely no doubt in my mind. James Holzhauer, Amy Schneider
and Matt Amodio are absolutely better players than Ken Jennings. It's not a
difficult or close question.
Consider this odd bit of trivia that I
only recently discovered. On their 28th appearance in their original
runs both Matt Amodio and Amy Schnedier passed $1 million in earnings. On his
27th appearance James Holzhauer passed two million dollars in
earnings.
It took Ken 30 games just to get to
the million dollar mark. On his 38th win he set the single day
record for $75,000 but he was at $1,321,660. By that point Matt Amodio had won
$1,518,601. Amy Schneider was basically tied with him at $1,307,200.
Ken after 40 games was at $1,353,461.
Amy was at $1,382,800 when her streak ended, which means she's at least his
equal but for reason I'll get to I think she's better.
With James Holzhauer the question of
whether he was better than Ken is almost a moot point. On just his 32nd
game he had $2,462,216. Ken Jennings must have a generosity in spirit that I
can't comprehend: if I were him I'd be sending a birthday card to Emma
Boettcher every day for the rest of both their lives. (I wouldn't mind seeing
her invited back for either an Invitational or Masters myself.)
So in their original runs all three of
the players immediately behind Ken money won and games won are clearly better
than him. And that's before you consider the postseason.
To repeat it took fifteen years for
Ken Jennings to win a postseason tournament of anytime. Both James Holzhauer
and Amy Schneider did so their first time out when each of them won the
Tournament of Champions. James Holzhauer
had to defeat the only player to that point in history who'd ever defeated him
to do so, Emma Boettcher and she made it very difficult for him. And while he
may have lost the GOAT to Ken Jennings he did beat Brad Rutter and Ken once.
That was before he won the very first
Jeopardy Masters in impressive fashion, though it did get tougher with each
advancement. And despite losing the second Jeopardy Masters to Victoria Groce
and Yogesh Raut, it doesn't change the fact that he did finish in third in the
quarterfinals and had the highest score in the semifinals. Considering that put
him ahead of the three former Masters that's impressive in its own way.
Amy has a different notch on her belt:
she's the first player in Jeopardy history to win the Tournament of Champions
in its new format of first to three wins. She did so against Andrew He and Sam
Buttrey who would become Masters in their own right because of their
performances. That's a more impressive triumph then James's in his victory even
if she has never done as well as him in the Masters.
And while Matt Amodio has joked about
his inadequacy in the postseason in the last few years, there's always been a
certain amount of self-deprecation. He did manage to become the first active
player to notch a win against James Holzhauer in the inaugural Jeopardy Masters
and he did beat Amy Schneider and Mattea Roach quite a few times in that
inaugural run even if he did finish first. And he did manage to win the second
Jeopardy Invitational Tournament over by beating some pretty impressive
players, among them Hannah Wilson and Roger Craig. That's still better than
Ken's track record no matter how you slice it.
It's unlikely that Ken will ever deign
to stop ducking a rematch and face off against the other challenger behind him,
as he spent between 2005 and 2020 doing so with everyone else who came before
him. But at this point in time its clear that while Ken may have won more games
then anybody in Jeopardy history he was never the greatest Jeopardy player of
all time. Brad Rutter had his number for fourteen years and James Holzhauer,
Matt Amodio and Amy Schneider have proved it multiple times and will again.
Perhaps someday soon, someone like Jamie Ding will add to that discussion and I
think Ken can appreciate better than anyone if it did.
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