Technically, he could never lose, no matter the question. After all, he is part of the program that's generating the questions, at this point. However, this begs the question; would the program, the matrix, let another program, said agent, kick jeopardy ass? What would be the real gain? Some shifting in 1's and 0's? This ytmnd is flawed.
Yup, this is one of the Ytmnds that hits that spot in the back of my brain. The part were i like to keep my hopes and dreams-they are made out of real things.