It was an idiotic item for a borrowing race. The item should be something that is guaranteed available, otherwise the competitor could be doomed to fail, for no fault of their own. What if the competitor likes someone who goes to another school? Not to mention, the running wouldn't anymore be up to the competitor if the liked person happened to be a slow runner. So, anyone else who needed to borrow a random small item would be given a huge relative boost.
He should have just picked that microphone girl/judge and be done with it. Might have as well made her suffer a little bit by pushing her to run faster and faster.