"It's boring to have the same guy win. I'm actively rooting against myself"

Ken Jennings is referring to his own success in the game program Jeopardy. He has won a record-breaking 74 consecutive video games and has actually ended up being a family name. His quote suggests that he understands his own success and is not taking it for given. He is humbly acknowledging that it is not exciting for the exact same person to win each time and is actively rooting against himself. This is a testament to his character and humbleness, as he is not taking his success for granted and is instead looking for a more interesting outcome. He is also lionizing for the other candidates and the video game itself, as he is not trying to control the program. His quote is a pointer that success ought to be commemorated, however not considered granted.