Tracy Flick Can't Win by Tom Perrotta

The thing about Tom Perrotta is that all of his characters are just this side of stereotypes: instantly recognizable, the kind of people we've known in our own lives and often have been, to one degree or another. Mostly Generation X, like Perrotta. (And like me, which means you may need to take what I just said with a grain of salt: we always love best the writers who mirror ourselves back.)

But the other thing about Perrotta, the more important thing, is that he seems to care for and understand all of those characters equally. His books tend to have multiple viewpoints - at least two major ones, such as in The Abstinence Teacher and Mrs. Fletcher, and often several secondary as well, as in Little Children and this book - and there's never a sense that he's on someone's side. Perrotta knows his people are flawed, and that they often do horrible things, but he's clear-eyed about them and lets us see them from inside.

No one is a villain inside their own heads. Perrotta's work is a great example of that.

Tracy Flick Can't Win is his new novel this year; it's substantially shorter than most of his books, barely two hundred and fifty pages of not-that-small type, broken into often quick-cutting chapters across multiple points of view. It's also the first time he's explicitly written a sequel; Tracy Flick was one of the main characters of Election. (You may have seen the movie, even if you never read the book.)

The central character is Tracy Flick, obviously. She went on strongly right after the events of Election: huge college successes, off to law school at Georgetown. Well on her way to her dream of being the first female President; entirely possible. But it's now twenty years later, and life got in the way. Tracy is a never-married single mother of an eleven-year-old daughter, living in suburban Green Meadow, New Jersey and the Assistant Principal of the local high school. It's not nothing: it looks a lot like success. But it's not what she wanted. It's not where she thought she would be.

She's not our only viewpoint character, of course. Almost equally important is Vito Falcone, the most famous Green Meadow graduate, a football legend who went on to have a short career in the NFL before an injury removed him from his dreams forever. His life has gone even more sideways recently, but he's taking steps to get back.

And then there's Kyle Dorfman, though we don't get deeply into his head. (I tend to think there isn't a "deep" there.) A tech-bro who cashed out and came back to Green Meadow, now the head of the Board of Education and looking for new things to disrupt and transform. If he has dreams, they're all about bigger and better start-ups, not running a high school, no matter what he tells himself now.

And Jack Weede, the principal of GMHS - Tracy's boss. He's had it tough - out for most of the past year with a major heart problem, a wife just coming out the other end of years of cancer treatments - and is looking forward to his own dreams. His retirement decision sets off most of the plot here; he and his wife have a dream they want to follow.

And also two members of the student council, Lily Chu and Nate Cleary, just starting out on their lives - smart and pretty focused but unaware of a lot. And Diane Blankenship, aka "Front Desk Diane," the one who keeps this whole school running and who everyone loves.

It's a large cast for a short book, but Perrotta keeps them from being stereotypes. They are types at times, but in the sense of "I know that guy." But they all have things they care about, and we understand and sympathize with all of them. Even the ones who want contradictory things.

What is the book about? Two things: Kyle wants the high school to have a Hall of Fame for some stupid tech-bro reason, and everyone else just goes along with that, running through a process to pick the first inductees over the course of a school year. And Jack is retiring at the end of that same year, so the Board and the Superintendent will be hiring a new Principal. 

Tracy wants the job, of course. Tracy is best-positioned for it, Tracy is the most qualified for it, Tracy has worked harder than anyone else for it - that's the story of Tracy's life.

The book is called Tracy Flick Can't Win. It covers most of an academic year. It's smart and thoughtful and full of people I think you will find immediately real. I won't tell you what happens to all of them in the end, but it's a Tom Perrotta book. Everyone screws up somehow, in different ways. Some are fixable; some aren't. And you don't necessarily get what you deserve. Just like life.