It’s boring to have the same guy win. I’m actively rooting against myself.
Meaning of the quote
Ken Jennings, an American celebrity, is saying that it gets boring when the same person wins over and over again. He wants other people to win instead of him, even though he is competing. He is actively trying to lose or not win, because he thinks it's better if someone else wins instead of him all the time.

About Ken Jennings
Ken Jennings is an American game show host, former contestant, and author who is best known for his long-running winning streak on Jeopardy!. He has also written several best-selling books and has appeared on other game shows. Ken Jennings holds numerous game show records, including the highest-earning American game show contestant and the longest winning streak on Jeopardy!.
More quotes from Ken Jennings
It’s boring to have the same guy win. I’m actively rooting against myself.
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