Ken Jennings shares ‘Jeopardy!’ secrets at the Crosscut Ideas Fest

The record-breaking, Edmonds-born winner and current host muses on the game’s transformation — and Crosscut's resident champ weighs in too.

Ken Jennings speaks at the Crosscut Ideas Festival

Peter Kafka, left, speaks with Jeopardy! host Ken Jennings on stage during the Crosscut Ideas Festival in Seattle. (David Ryder for Crosscut)

For me the most startling revelation from last weekend’s Crosscut Ideas Festival had nothing to do with AI, climate change, the 2024 election or Donald Trump. It was when Seattle native Ken Jennings — the record-breaking Jeopardy! champion and now-host — mentioned in passing during his interview with Vox correspondent Peter Kafka that the producers of the game show had once considered randomizing the positioning of Daily Doubles on the game board, but ultimately rejected the idea.

Meaning their locations aren’t random, and never have been, as I’d assumed during half a century of watching the show. (And being on it; more on that later.)

Instead, someone behind the scenes chooses which clues will be DDs. This confession came during the most absorbing part of the interview: Jennings’ discussion of the professionalization of the venerable game show, what he calls its “Moneyball” era, and the ways game play and the contestant experience have been changed over the years by the internet, social media in particular.

Jeopardy! has aired off and on – but mostly on – since 1964. Its first incarnation, through 1975, was hosted by Art Fleming, whose prep-school, Newport Regatta vibe helped make the show a daytime-TV hit. Alex Trebek took over for the 1984 syndicated reboot, and by the time his final episode aired, a month and a half after his November 2020 death, he was well-established as one of the most iconic figures in television history.

But Trebek’s fame was due not just to his longevity, but to the transformation of J! itself. The show was always fervently beloved by its fans, but for much of its history had about the same cultural visibility as, say, Hollywood Squares. But Jennings’ record-breaking, still-unsurpassed 2004 streak of 74 consecutive wins (the second-longest streak of 40 belongs to Amy Schneider, from 2021-22) was surely the event that made the show a mass phenomenon — the level of pop-culture dominance at which an emcee change becomes a major multi-week news story rather than a 300-word brief in Variety. (Go ahead, name a Price Is Right contestant.)

What Jennings was too modest to mention on Saturday was just how the sportification of the show may have been, in part, a result of his unprecedented success. If the show had retained its lower profile, if Jennings hadn’t become famous for his streak, would anyone have gone to such great lengths to surpass it by employing a suite of tools that Jennings never had access to?

When Jennings stepped into hosting duties in 2021, he inherited a game that had been transformed by the moneyball approach that has altered professional sports. Winning streaks have proliferated, and the appearances of defending champions for 10, 20, 30 or more games have become more and more common.

I was one of the few in a position to challenge Jennings’ record, if briefly. If you were watching KOMO-TV at 7:30 p.m. on July 12, 2017, you would have heard announcer Johnny Gilbert introduce “a writer and editor from Seattle, Washington.” If you kept watching, you would have seen the first of what would be my three wins. (I lost the fourth to Deborah, an educator from Cleveland, Ohio.)

Former host Alex Trebek and Crosscut copy chief Gavin Borchert on the set of Jeopardy! in July 2017. (Courtesy of Gavin Borchert)

As Jennings noted in his Festival appearance, the online resources available to contestants serious about success have expanded hugely in the past few years. Since Jennings’ streak, many who seek to break his record have explored gameplay in depth — the deep analytics, the game theory, the betting strategy — and even created a searchable online archive of hundreds of thousands of clues and responses. The internet is the place to start if you want to know all there is to know about the Coryat Score or the Forrest Bounce.

But all that has burgeoned only since 2017. Instead, I thought it might be most efficient to review information easily organized by lists (amendments to the Constitution, Oscar winners, monarchs of England, the periodic table), which I guess might have helped if any categories in those subjects had come up. But the best way to prepare for J!, in my opinion, is simply to watch it a lot. For 45 years, if possible.

My second game I won, I admit, only because the super-nice guy from Virginia to my left whiffed soul-crushingly on a Daily Double. I did miss in the Final Jeopardy! round (“Who is Sylvester Stallone?”), but held on for the win. My third game and the final taping of that day — they tape five shows each on Tuesday and Wednesday of selected weeks — went a little more smoothly and, yes, more buzzer experience is a significant advantage returning champs enjoy. (It’s about the timing, any alum will tell you, since if you ring in during the reading of the clue, you get momentarily locked out. Jennings mentioned this on Saturday too: Hit that sweet spot just as he’s reading the clue’s last syllable.)

I did “respectably,” is how I describe it. I never “ran” a category (correctly answering all five clues, though I did get four right in PAINTERS: M), nor achieve a “runaway” (in which you enter FJ! with more than double the second-placer, so even if they bet everything and win, you can still win if you bet $0).

As for Daily Doubles, in my four games I hit two (“What is rum?” “What is a 21-gun salute?”) out of a possible 12. Final tip: In recent seasons it’s been demonstrated, in abundance, that DD betting is what separates J! minnows from whales. Go for it.

Jeopardy! champion and host Ken Jennings signs books during the Crosscut Ideas Festival. (David Ryder for Crosscut)

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