In the original 'October Surprise', three weeks before Election Day 1964, President Lyndon B. Johnson discovers that police have arrested his top aide of twenty-five years, Walter Jenkins, in a public bathroom sex sting. Worse, the media uncover that it's not Walter's first arrest. After Johnson orders an FBI investigation to establish how Walter passed his White House background check, the two can no longer be observed interacting.

When students leave an elite university for winter break, a tightly wound astronomy professor and a laid-back football coach are forced to team up for the local Christmas Bar Trivia Tournament. Initial clashes turn into mutual appreciation as the two discover that life's surprises might be more important than always knowing the right answer. As the competition heats up, friendships are tested and secrets surface, revealing how much more is at stake than just bragging rights.