Carleton Grad Leans on University Smarts to Win on Jeopardy

By Elizabeth Howell

Carleton University graduate Grant McSheffrey racked up nearly US$70,000 (about C$93,000) as a three-time Jeopardy champion from March 14 to 17.

The longtime BlackBerry employee, trivia buff and Jeopardy fan says he pulled out his Carleton computer science training to help him get through some of the tougher questions.

“Programming is a lot about looking at a jumble of stuff, trying to pull out the important bits and putting them back together in a way that makes sense,” McSheffrey said in an interview before his winning streak came to an end. “In a lot of ways, the clues on Jeopardy were the same.”

One example was a clue asking about Carlos Jobim, which McSheffrey guessed (correctly) had to do with the city Rio de Janerio, Brazil. The clue said that Jobim had written a song about a particular city in 1957, and that today the airport in that city is named after him.

McSheffrey had never heard of Jobim, but reasoned it sounded like a Portuguese name. From there, he thought about major Portuguese cities and remembered the famous Frank Sinatra tune, “Girl From Ipanema.” Ipanema is a neighbourhood in Rio.

McSheffrey spent 10 years at Carleton (1997 to 2007), finishing his undergrad part-time while working full-time in the computer science industry. His first job was at a startup company called EmpowerTel Networks, and then he moved to another startup eventually bought by IBM. He joined Research In Motion (now BlackBerry) in 2008 and today works on BlackBerry Messenger Enterprise for iPhone, which uses secure communications for business applications.

Carleton Provided Connections

McSheffrey credits his time at Carleton. not only for helping him to think through problems critically, but for giving him the connections he needed to get hired in the industry. For example, his job at IBM came after a recommendation from a co-op student he knew at Carleton who heard about an open position and suggested McSheffrey apply for it.

“I liked the general approach of Carleton,” McSheffrey said. “It didn’t seem to be as structured or rigid as some of the other university programs. Carleton, they did new things – such as object-oriented programming – before anybody else. That was well before I started studying there, but it was indicative of the kind of approach they took.”

McSheffrey has been a Jeopardy fan since childhood and it took him roughly five years to get on the show. On his first attempt, he passed an online test, was invited to an audition at one of eight American cities (he chose New York City), but was not chosen to appear on the show. His second attempt at the test saw him pass, but he was not asked to audition.

So it was on his third attempt that McSheffrey finally found himself passing the audition and being filmed at the Jeopardy set in Los Angeles in December.

As Ottawa media and Twitter accounts lit up about his repeated wins, McSheffrey kept his thoughts to himself about how long his winning streak might last. There is no limit on Jeopardy wins anymore, he said – it’s just a matter of enduring as long as you can.

“Everything flew by. I barely remember anything,” he said of his time on stage. “I thought there were a few things I remembered, but most of those few things I remembered incorrectly.”

Focused Competition

McSheffrey described his competition as friendly, but focused. He also said that he got a few lucky breaks. In one episode, the first category was sports – there were three NHL questions and a question about the Toronto Blue Jays, all categories that many Canadians would know well. On top of that, McSheffrey drew a question about Newfoundland that same evening.

Married with two children, McSheffrey joked that he does not have an extraordinary memory. But he is interested in certain popular topics on Jeopardy, such as geography, which he said assisted with the win.

Jeopardy is hosted by former Ottawa resident Alex Trebek, who made several references to McSheffrey’s citizenship on the show. There was a brief time when privacy concerns prevented Canadians from applying, Trebek said during one episode, but added that he is glad to welcome Canadians like McSheffrey again.