Bradford Rutter is the biggest winner in the history of Jeopardy! and perhaps its greatest player, having amassed over $3.2 million at the tender age of 27, becoming the biggest quiz show winner in history.

Brad has won the 2001 Tournament of Champions, the 2002 Million-Dollar Masters, and the 2005 Ultimate Tournament of Champions, making him the only 3-tournament winner in Jeopardy history.  When he played Ken Jennings and Jerome Vered in the three-day finals of the Ultimate Tournament, he beat both Ken and Jerome three games in a row.

No one, in fact, has ever beaten Brad.  So, you ask me, he kinda deserves his own interview.

The following was recorded at a small Italian restaurant in Beverly Hills, walking distance from the lush Beverly Hilton, where Jeopardy! bunked him during two of his tournament wins.  I had only begun working on Trebekistan and had no real idea what the book would eventually look like.

Brad: So I can trust you with this, right?  I mean you’re not gonna give away any trade secrets here.

Me: Of course not.  And if something slips, and you don’t want it in, that’s fine.  I’ll be the only one who knows.  That could work to my advantage if we ever play each other.

Brad: So if I say something like [something completely unrepeatable] —

Me: [laughing] I can promise that won’t be in the book.

Brad: Cool.  Y’know, when I heard you were writing this, I thought, "this is the perfect guy."

Me: I see.  So the tape goes on, and the flattery begins.  You’ll go far in Los Angeles, my son.  

Brad: You’re very kind.

Me: First question: that Ultimate Tournament final had to be a blast.  And with the closed set, it must have been a uniquely shared experience.  You stay in touch with your victims?

Brad: Sure.  Ken and I email back and forth, and I gave Jerome a call now that I’m in town.  But you know as well as anybody about how people stay in touch.  It’s like almost the whole Masters group.  It’s fun for us all to get together on the east coast for the regional dinners when I’m out there.  India puts those together, those are fun.  

Me: Speaking of Ken, we’ve emailed a few times.  He seems like a pretty cool guy.  Totally has his head on straight for somebody who pulled off what he did.

Brad: No question.  Although I don’t know how he does that artistic stuff with the light pen.

Me: What’s up with that?  Who wakes up thinking, "today I’ll try out 24-point Helvetica?"

Brad: That’s almost amazing as winning 70-odd games.

Me: Me, I just try to write "Bob," and it looks like I have some kind of disorder.

Brad: Well, that’ll teach me to assume.  [Grins.]

Me: So.  [Pausing, finally catching the wicked glee in Brad