Tracy Flick, now an assistant principal in New Jersey, once again finds herself embroiled in high school politics, as she works to convince the school board that she’s the right choice to replace the retiring principal. But while she gives her support for a new school Hall of Fame in exchange for support, she isn’t the shoo-in she thinks she should be. Things change at the initial Hall induction ceremony, where things go sideways and she earns the position she feels she deserves. The only question is if it was worth it?
I first became acquainted with the character of Tracy Flick in the 1999 film adaptation of Tom Perrotta’s novel Election, where a young Reese Witherspoon portrayed the overqualified student running unopposed for student body president until a male teacher plots against her. In Tracy Flick Can’t Win, Perrotta brings the character back for another run through the wringer as an adult who, while highly successful, has never met her own expectations for her where she should be in life due to life getting in the way. This time around, she once again sees herself losing out on something to which she feels she’s entitled to a football hero and decides to cut loose. In the end, she gets the position she wanted, but pays a heavy price. I would like to read Election one day and rewatch the film to see how they match up.

[…] I became reacquainted with the Tracy Flick character last fall, when Perrotta released the sequel Tracy Flick Can’t Win. This tale unfolded much as I expected it to, from my recollections of a 25-year-old film. I […]