If you look up the season 1989 episode 45 of Jeopardy! (March 3 of that year) you’ll see what I looked like at age 42. I had studied hard for that appearance, but it turned out that I neglected to master a critical aspect of the game.
The rules were a bit different than they are now. Back then you could win up to five times in a row and then you were retired. Starting in 2003, you could keep going as long as you kept winning.
If you came in first place, or tied for first place with a greater-than-zero score, you got to keep the money you earned and come back and play in the next episode. If you didn’t win, you received no money. You were offered consolation prizes — which you paid taxes on, if you kept.
From the beginning of the contest, it was a back-and-forth match with all of us getting some answers correct and missing others. The part of the game that I hadn’t mastered was how much to bet during Daily Doubles and Final Jeopardy. I thought it was fairly straightforward. I was wrong.
Early in the second half of the game, I landed on the Daily Double in “Astronomy” when I chose the bottom answer of that category — meaning it would be more difficult to get correct than if it had been one of the earlier answers. Choosing the Daily Double allowed me to bet any amount up to the total amount of my accumulated score. If I missed the question, the other contestants didn’t get a chance to get it correct.
While I haven’t seen a video of this episode in a while, this is what I remember: I was in third place going into the question, and if I bet everything and got it correct, I’d temporarily be in first place — with about a third of the game still to go.
If I bet everything and got it wrong, I would be wiped out and there was insufficient time left to recover and have a chance to win the game. If I bet less than everything, I’d at least have something left if I missed the question and could fight on from there.
Astronomy wasn’t my best subject. While I had taken an Introduction to Astronomy class in college more than 20 years previously, I didn’t remember much of what I had learned. I knew the planets in order (back then Pluto was still a planet!) and the names of some of the constellations. I certainly didn’t know the names of all the moons of Saturn and Jupiter. There were some questions I could answer, but not many.
The question became: How much should I bet? To simplify, I’ll give you three choices to consider:
A. “True Daily Double” — meaning I bet the maximum I could. This gives me the best chance to win the game if I get it right and wipes me out if I get it wrong.
B. Bet about 2/3 of my total — saving some money “in case” I got the question wrong. And I believed that I was probably going to get the question wrong.
C .Bet a minimal amount so my score wasn’t affected much whether I got it correct or not.
What would you bet?
I bet option b. The answer was something like: “Built on the palace grounds of Charles II beginning in 1675.”
I guessed, “What is the Greenwich Observatory?” and it turned out to be correct. I never knew when or where that observatory was constructed, but it seemed to be a momentous enough event to be worthy of a Jeopardy! question. My answer turned out to be correct — but my bet turned out to be wrong.
What I didn’t sufficiently realize at the time was that to win at Jeopardy!, you have to take your chances when they come. If I had missed the question, even if I had $1,000 left to play with, I would essentially be out of the game. Since I wanted to win (otherwise why would I be there?), I should have bet the farm and taken my chances.
As it turned out, had I bet everything and the rest of the game went as it did (big assumptions!), I would have tied for the lead following Final Jeopardy and come back to play on the next episode. Since I hadn’t bet everything, the leader going into Final Jeopardy was able to bet enough to shut me out if I bet everything and we both got the Final Jeopardy question right (which is what happened.)
So, I came in second place — got a Lazy Boy recliner (which didn’t survive the cut when I next got married) and a framed lithograph (which did). My first day of competition turned out to be my last day.
After the round was over, it was easy to calculate that I would have tied had I bet the Daily Double properly. While I couldn’t have known that was going to be the result when I made the bet, I should have been able to figure out that if I was going to win, betting everything on the Daily Double gave me the best chance. It was a small chance (I first had to get a difficult question correct) but it was my best chance.
Oh well. Spilt milk, and all that.
In case you want to test yourself on the Final Jeopardy question from that day in the category of “American Revolution,” the answer was:
One of the two people Paul Revere was attempting to warn when he made his famous ride.
While I didn’t know the correct question before hearing the answer, I knew that Revere’s ride was in the Boston area and one of the revolutionary firebrands in that part of the country was Samuel Adams, so that was what I guessed (in the form of a question.) It turned out to be correct and John Hancock would also have been correct.
I never watched the following episode to guestimate how well I would have done had I bet correctly and gone on. All in all, even though I didn’t win, I felt I had done pretty well — with one exception.

Do you have so few things about
Gambling, that you so far back
to when you lost on jeopardy. I
know writing a weekly column
is difficult, but can’t you do
better?
I thought it was a very interesting column. I give Bob or anyone who goes on a game show a lot of credit. It would be very easy to make a complete fool of yourself.
Robert, I understand your sentiment but think you are missing the point. The whole essence of Bob’s posts are to encourage you to think like an advantage player – and this one is also about gambling with the right mindset. If you listen in to Bob and Richard on Gambling With An Edge, you’ll find many instances where a smart approach can increase your expected return. I’m a casual but enthusiastic gambler, and am grateful to have profited by thousands of dollars over the years by thinking through similar situations using the strategies that I have gleaned from gambling theory. I recommend Million Dollar Video Poker to give a great insight into how professional gamblers think. I believe you’ll then realize how relevant this latest post was.
I did a search, tried to find it but couldn’t. Is there a link? Realizing we might not recognize the 1989 version of Bob nor the name he competed under (real name?).
IMHO, going on Jeopardy (or any game show) would be a risky proposition. Kudos to Bob for doing it and sharing his results. He did good, though.
OMG I found it!
Not the telecast, but the archives, interactive, just like the Jeopardy board on TV, every Topic, Answer and Question, which contestant got the answer (actually the “question”), both Jeopardy and Double Jeopardy rounds, winning totals, prizes they got, everything…except the telecast. Contestants were Bill, David and Chris (no last names given as on the show, can probably figure out which one was BD from the questions he told us he got right). I have 11 telecasts to go thru, Feb 21 thru March 7th 1988. Bob’s show was taped on Nov. 15, 1988. Looks like they taped 3-4 episodes a day back then, weeks/months before we saw them on TV.
Having so much fun going through all the topics, answers, and questions.
I’m gonna keep digging for that telecast! LOL.
I posted the TV telecast dates wrong. Telecasts were 1989 as Bob’s was, not 1988. The tapings were done in late 1988, months prior to being telecasted (is that a word?). Sorry,
Now they typically tape a weeks worth of episodes in a day. Morning and afternoon sessions are typically 3 and 2 episodes. If you get the (free) tickets to attend you get to watch one session, 2 or 3 shows.
Nice story
I am from Boston and would have got the last question right
But not the previous one
Good for you
Thanks, Bob, for sharing your experience and perspective while competing on “Jeopardy!” I, for one, appreciate your insights on gaming the system, whether the system in question is VP or not.
I have a question unrelated to the game show… Regarding the evolution of your play at Dotty’s over the years, has the increase in the W2 threshold changed your game and/or stakes? If so (and assuming you’re still playing there), how has it changed? I look forward to your insights…
Why do you even care? You low roller betting $1.25 a hand won’t earn anything substantial.