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First Cigar: Brad Rutter 

Brad Rutter

Answer: This 61-mile-long tributary of the Susquehanna River runs through the heart of Lancaster County, Pennsylvania.

Question: “What is the Conestoga River?”

It takes all of five minutes in a conversation with Brad Rutter to discover why he has the jam to make millions of dollars as a Jeopardy champion.

“Did you know the term ‘stogie’ comes from the Conestoga River?” Rutter says of the river flowing through his hometown. “In the early 1900s, it was the biggest cigar-producing part of the country.”

Now that’s a Jeopardy king.

The 44-year-old Rutter grew up the older of two brothers, the son of a stockbroker and homemaker, and has won $5.1 million since 2000 playing the iconic television quiz show. His trade is knowledge, and he deals in it with great abundance, most recently as a host on ABC’s “The Chase,” a game in which contestants match wits with one of several accomplished know-it-alls, including Rutter, for big money.

The gift of curiosity came early to Rutter, who watched Jeopardy with his parents starting at the age of six. That curiosity – and a developing taste for the finer things – escalated to premium cigars at the age of 18 in 1996, about the time of the first cigar boom in the U.S.

“My first cigar was either an Onyx or a Montesino. I recall thinking ‘this tastes like chocolate,’ which was amazing to me. I got the point immediately.”

And he scored many more points as he grew up, becoming a serial game show contestant and racking up victories.

Rutter talked with Cigar Snob about navigating the world of Hollywood sets, cigars and his life.

Getting schooled

My parents had watched the old Jeopardy with Art Fleming as host, and so when it came back with Alex Trebek, I was watching with them. I’ve been watching it ever since. I think I learned a lot of things by osmosis, and I’ve always enjoyed knowing stuff. By the time I got to high school I found myself knowing all the answers [on the show]. In high school I was on our Quiz Bowl team and once we started to be ranked nationally, I knew I was pretty good, and a lot of that came from watching Jeopardy. In college, we sat around and watched Jeopardy and I would know 90 % of the answers and my friends would say, “you need to get on that show.” I said, “I know.” I was doing better from the couch than the contestants, although that’s easier than actually playing up there because of the pressure. I went to the test for the show, which is just a TV audition. They want to see if you are good at taking direction and other things that are basic to television. And if you come across as your normal self and not nervous, that’s key to getting selected. I am one of those weird people who never had a fear of public speaking, though. I wouldn’t say I’m smarter than anyone who has done well, I just handle pressure better.

The first time

I won $55,000 in five episodes, and they were all shot on the same day, a week’s worth of episodes, on a Monday. I had come in on a Friday and they shot that day but I didn’t get on. The nerves were incredible, I don’t know that I would have won if I had played the first day. But I had time to watch and see how it was done.

I won the $55,000 and two cars, choosing from Chevrolets. One of the choices was a Corvette, which I wanted but they were out. The choice came down to a Suburban or Camaros and I took the Camaros. I gave one to my brother, who is two years younger than me. The cars came about two weeks after I filled out the paperwork and we went to the local dealership to pick them up. The money came in a check that I received three months later. At the time, I was 22 and had quit college [Johns Hopkins University] and was living with my parents and working at a CD store. It was a very Gen X thing. I went and rented an apartment in Lancaster with two bedrooms. That was my idea of living it up. I grew up in a home in which investing was encouraged, so I was smart with my money.

How he learns

I’m an autodidact. I have always learned better discovering stuff on my own. I did well in high school but I’m always learning things from reading or watching documentaries. I learn better when I am interested in something, but I’ve always been interested in a lot of things. I read books, at least 10 to 12 a year, usually something I hear about or get a recommendation for. I go online to learn more about current events. On The Chase, we have a lot of questions on pop culture, so I make an effort to go to Spotify and check out the top 50. On one of The Chase episodes, I had been reading up on Camila Cabello, and the question was what group was she in before she went solo. I missed it, though; it was Fifth Harmony.

He does sneak into your local trivia contest…

One of my friends talked me into it, just recently. I was in Philadelphia and a couple of friends said, ‘we should go to quiz night.’ It was at a local bar and yes, we won. I huddle in a corner so I don’t get recognized. Part of the subterfuge was that I’m not the one taking the answer sheet up.

He’s also an actor

I had an audition for [Apple TV+’s] Morning Show as Jennifer Aniston’s dad in a flashback scene. I didn’t get the role and I don’t think they ever used that scene. I enjoy auditions, you get to play someone, which is great. A wise person said ‘as an actor, your job is auditioning, not shooting.’ It helped that I didn’t get into acting and auditions until I was in my late 20s and had been on Jeopardy. I had Jeopardy money in the bank and didn’t have to beg off a shift waiting tables to go to the audition. I can’t imagine growing up and wanting to be an actor and going through all the rejection, because you get rejected more than you get accepted.

Cigars came early

It was the 90s and the whole lounge revival thing was going on and cigars were part of that. We were the only 18-year-olds going to cigar lounges and enjoying it and knowing cigars. I still go to the shops when I go back to Lancaster to visit, which I do four times a year. In Los Angeles, where I live, I go to Cigar Warehouse in the Valley. The weather here is so good I can smoke outside, I like to go in the backyard, put in some earbuds, smoke and listen to a podcast. I also like going to the lounge to watch a football game. My cigar trivia game isn’t all that good, but I know what I like. I have about an 80-count humidor, and I keep it stocked. My favorite is the Montecristo No. 2, which is my special occasion cigar. Whenever I am in Canada or Europe, I pick up a Cuban version. What is a special occasion? Winning a big Jeopardy tournament or the birth of a niece or nephew.

I have recently gotten into Micallef, because my girlfriend is doing social media work for them.

What’s next

It would be great if The Chase is renewed {for a 4th season]. But I’m going to do some traveling this year, internationally, I have a landmark birthday coming up and I won’t say which one (Ed note: we will – #45 in January) and I always wanted to get to Australia.

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