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Tracy Flick Can't Win
Table of Contents
About The Book
“Tom Perrotta is…one of the great writers that we have today. I love this book.” —Harlan Coben
An “engrossing and mordantly funny” (People) novel about ambition, coming-of-age in adulthood, and never really leaving high school politics behind—featuring New York Times bestselling author Tom Perrotta’s most iconic character of all time.
Tracy Flick is a hardworking assistant principal at a public high school in suburban New Jersey. Still ambitious but feeling a little stuck and underappreciated in midlife, Tracy gets a jolt of good news when the longtime principal, Jack Weede, abruptly announces his retirement, creating a rare opportunity for Tracy to ascend to the top job.
Energized by the prospect of her long-overdue promotion, Tracy throws herself into her work with renewed zeal, determined to prove her worth to the students, faculty, and School Board, while also managing her personal life—a ten-year-old daughter, a needy doctor boyfriend, and a burgeoning meditation practice.
But nothing ever comes easily to Tracy Flick, no matter how diligent or qualified she happens to be. Her male colleagues’ determination to honor Vito Falcone—a star quarterback of dubious character who had a brief, undistinguished career in the NFL—triggers memories for Tracy and leads her to reflect on the trajectory of her own life. As she considers the past, Tracy becomes aware of storm clouds brewing in the present. Is she really a shoo-in for the principal job? Is the Superintendent plotting against her? Why is the School Board President’s wife trying so hard to be her friend? And why can’t she ever get what she deserves?
A sharp, darkly comic, and pitch-perfect chronicle of the second act of one of the most memorable characters of our time, Tracy Flick Can’t Win “delivers acerbic insight about frustrated ambition” (Esquire).
There was another front-page story in the paper. For months it had been an almost daily occurrence, one powerful man after another toppled from his pedestal, exposed as a sexual predator: Harvey Weinstein in his bathrobe, Bill Cosby with his quaaludes, Matt Lauer and his secret button; the list went on and on. It was a satisfying spectacle—a small measure of belated justice—but it was troubling too, because it kept stirring up memories I would have preferred to leave alone, as if I were being asked to explain myself to the world, though I wasn’t exactly sure who was doing the asking.
That morning’s scandal was celebrity-free, and for me, at least, even more disturbing than usual: a “beloved” drama teacher at a fancy boarding school accused of having “inappropriate sexual and romantic relationships” with several former students, the allegations stretching all the way back to the 1980s. The teacher—he was retired now, living quietly in Tulum—denied the charges; a lawsuit had been filed against the school, its trustees, and three different headmasters who had “abetted the decades-long cover-up.” There was a black-and-white yearbook photo of the teacher in his younger days—he was standing onstage, boyish and shaggy-haired, directing a student production of Oklahoma!—along with color photos of two of his accusers. The women were attractive and successful, both around my own age—a dermatologist and an art historian—and they gazed at the camera with eyes that were somehow steely and wounded at the same time. He groomed me so skillfully, the art historian said. He told me exactly what I wanted to hear. The dermatologist had a bleaker assessment: He stole my innocence. It pretty much ruined my life.
“Mom,” Sophia said. “Are you okay?”
I looked up from the newspaper. My ten-year-old daughter was watching me closely from across the table, the way she often did, as if she were trying to figure out who I was and what was going on in my head. I’d never had to do that with my own mother.
“I’m fine, honey.”
“It’s just—you looked a little angry.”
“I’m not angry. That’s just how my face gets when I’m thinking.”
She considered this for a second or two, then wrinkled her nose.
“There’s a name for that,” she said. “It’s not very nice, though.”
“So I’ve heard.” I glanced at the wall clock. “Finish your oatmeal, sweetie. We need to get moving.”
Aside from the handful of people who knew about it at the time—my mother, the Principal, my guidance counselor—I never talked to anyone about what happened to me in high school. Until the past few months, I hardly even thought about it anymore, because what was the point? It was ancient history, a brief misguided affair—that’s the wrong word, I know, but it’s the one I’ve always used—with my sophomore English teacher, a few regrettable weeks of my teenage life. It wasn’t that big a deal. We made out a few times, and had sex exactly once. I realized it was a mistake, and I ended it. My life wasn’t ruined. I didn’t get pregnant, didn’t get my heart broken, didn’t miss a step. I graduated at the top of my class, and went to Georgetown on a full scholarship.
It was Mr. Dexter who couldn’t handle the breakup, and kept pestering me to get back together. My mother found a note he wrote on one of my essays—it was a little unhinged—and she went to the Principal, and Mr. Dexter vanished from the school, and from my life. It was all very sudden and surgical. I guess you could say the system worked.
As a grown-up—as a parent and an educator—I had no doubt that what he did was wrong, and that his punishment was just. In the privacy of my own heart, though, I couldn’t manage to hate him for it, or even judge him that harshly. There was a mitigating factor at work, an extenuating circumstance. It didn’t exonerate him, exactly, but it made him less culpable in my eyes, more worthy of sympathy or compassion, whatever you want to call it.
That circumstance was me.
The thing you had to understand—it seemed so obvious to me at the time, so central to my identity—is that I wasn’t a normal high school girl. I was unusually smart and ambitious, way too mature for my own good, to the point where I had trouble making friends with my peers, or even connecting with them in a meaningful way. I felt like an adult long before I came of legal age, and it had always seemed to me that Mr. Dexter simply perceived this truth before anyone else, and had treated me accordingly, which was exactly the way I’d wanted to be treated. How could I blame him for that?
That was my narrative, the one I’d lived with for a very long time, but it was starting to feel a little shaky. You can’t keep reading these stories, one after the other, all these high-achieving young women exploited by teachers and mentors and bosses, and keep clinging to the idea that your own case was unique. In fact, it had become pretty clear to me that that was how it worked—you got tricked into feeling more exceptional than you actually were, like the normal rules no longer applied.
It gnawed at me that summer, the possibility that I’d misjudged my own past, that maybe I’d been a little more ordinary than I would have liked to believe. But even if that were true, there wasn’t anything I could do about it. There was no injustice to expose, no serial abuser living it up in a tropical paradise.
Mr. Dexter didn’t just lose his job because of me; he lost his wife and a lot of his friends and his self-respect, and he never really got back on track. After he stopped teaching, he managed his family’s hardware store until it went out of business, and then he became a home inspector. He got married a second time in his forties, but that hadn’t worked out, either. I knew this because he wrote me a letter in 2014. He was in the hospital at the time, being treated for an aggressive form of prostate cancer, and wanted to apologize to me before it was too late. He said he still thought about me sometimes, and wished we’d met under different circumstances.
I’m not a bad person, he said. I just made some horrible decisions.
He was fifty-five when he died. As far as I was concerned, he could rest in peace.
Sophia was attending soccer camp that week at Green Meadow High School, where I served as Assistant Principal. I pulled up in the horseshoe driveway by the practice field, idling just long enough to watch her sign in with a clipboard-wielding counselor, and then trot onto the grass, where she was greeted with a fanfare of happy shrieks and joyful shimmies from the other girls, as if they hadn’t seen her for years. I felt a familiar pang of separation, the melancholy awareness that my daughter’s real life—at least her favorite parts—took place in my absence.
I’d never been like that as a child, a valued member of the pack, showered with affection, protected by the safety of numbers. I’d always been a party of one, set apart from the other kids by the conviction—I possessed it from a very early age—that I was destined for something bigger than they were, a future that mattered. I didn’t believe that anymore—how could I, my life being what it was—but I remembered the feeling, almost like I’d been anointed by some higher authority, and I missed it sometimes. It had been an adventure, growing up like that, knowing in my blood that something amazing was waiting for me in the distance, and that I just needed to keep moving forward in order to claim it.
The only thing waiting for me that morning was my cramped office in the empty high school, the unceasing demands of a job I’d outgrown. It was an important position, don’t get me wrong—I had a lot on my shoulders—but it was hard to stomach being the number two again, after savoring an all-too-fleeting taste of real authority.
Three years earlier, I’d taken over as Acting Principal after my boss, Jack Weede, had suffered a near-fatal heart attack. He was sixty-five at the time, and everyone assumed he would pack it in, and that my promotion would become permanent. But Jack surprised us all by coming back; he couldn’t let go of the reins. It was his call and I didn’t hold it against him—retirement had never struck me as much of a prize, either—but the ordeal had taken a toll on him, and a lot of his workload ended up landing on good old Tracy’s desk.
Even on a slow day in early August, there was more than enough to keep me busy. I started by combing through the analytics from our most recent round of assessment tests, trying to spot gaps in our curriculum, and offer some low-impact, last-minute suggestions for addressing them. We’d been slipping a bit in the statewide rankings—not badly, but just enough to cause some alarm—and we needed to take some concrete measures to turn that around before it became a serious problem.
After that, I scoured a stack of old résumés in search of a long-term substitute for Jeannie Kim, our popular (if slightly overrated) AP Physics teacher, who was taking maternity leave in January. An incompetent sub isn’t a huge problem if they’re only in contact with the students for a day or two, but Jeannie was going to be out for an entire semester.
If I’d left it up to Jack, he would’ve waited until the last minute, hired the first warm body he could get his hands on, and then shrugged it off if something went wrong. It’s hard to find a good sub, Tracy. There’s a reason those people don’t have real jobs. But I wasn’t about to let that happen, not if I could help it. Our students deserved better. It was easy to forget, when you were a grown-up and high school was safely in the past, how it felt to be a captive audience, the way time could stand still in a classroom, and one bad teacher could poison your entire life.
Reading Group Guide
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Tracy Flick is back and, once again, the iconic protagonist of Tom Perrotta’s Election is determined to take high school politics by storm. Now in her forties, Tracy is a hardworking Assistant Principal at a public high school in suburban New Jersey. Feeling stuck and underappreciated in midlife, Tracy gets a jolt of good news when her school’s longtime Principal abruptly announces his retirement.
Excited by the opportunity to claim the top job, Tracy throws herself into her work with renewed zeal. At the same time, the hiring process triggers troubling memories about her own high school experiences, as well as her more recent personal and professional disappointments. As she broods on the past, Tracy becomes aware of storm clouds brewing in the present . . . Is she really a shoo-in for the Principal job? Is the Superintendent plotting against her? Why is the School Board President’s wife trying so hard to be her friend? And why can’t she ever get what she deserves?
Topics & Questions for Discussion
1. In chapter 1, while reflecting on the importance of her administrative work at Green Meadow High, Tracy Flick thinks: “It was easy to forget, when you were a grown-up and high school was safely in the past, how it felt to be a captive audience, the way time could stand still in a classroom, and one bad teacher could poison your entire life” (page 7). How does this idea—of the outsize impact high school experiences have on people’s adult lives—echo throughout the book? Do you agree with Tracy’s assessment? Name and discuss one example of an experience that has followed one of the adult characters into adulthood.
2. Whose idea is it to start the Hall of Fame? Consider what we know about this character and their previous career by the end of the novel; why might they have been drawn to the concept of a Hall of Fame?
3. When Tracy Flick first hears about Vito Falcone, she thinks, Ugh, I know that guy (page 52), even though she’s never met him. What does she mean? What kind of guy does Tracy understand Vito to be, and why does she find this archetype frustrating?
4. Throughout the novel, Vito suffers from headaches, memory loss, and disorientation. What is causing Vito’s symptoms? Consider the fact that the very thing Vito is famous for in Green Meadow—his track record in varsity football and his short career in the NFL—is causing him pain in his personal life. Why is this apparent contradiction meaningful to the story?
5. Tracy Flick struggles with negative self-talk. As she meditates (pages 98–99), she compulsively plays two phrases over in a loop, You failed, and You did the best you could, before realizing both are true. Why is coping with failure so difficult for Tracy? Where do her impossibly high expectations of herself come from?
6. Consider Jack and Alice Weede’s relationship. What is the secret Jack has been keeping from his wife? After it is announced that Diane Blankenship will be inducted into the Hall of Fame, Alice reveals that she’s known Jack’s secret all along. Why do you think Alice had not confronted Jack previously?
7. In a conversation with Tracy, Marissa confides that Kyle has cheated on her previously, and that, while in her twenties, she once slept with a married man. In response, Tracy tells a secret of her own—that she had a relationship with a teacher when she was fifteen. Based on this conversation, what about her experience with Mr. Dexter do you think hurt Tracy the most?
8. Who is Reggie? Why doesn’t the Selection Committee (other than Lily) consider Reggie to be a serious candidate for the Hall of Fame, even though he and Vito were both football stars at Green Meadow High? What role does race play in the difference between Vito’s career and Reggie’s?
9. Consider the rapport between Tracy and Lily. How does Lily’s opinion of Tracy differ from that of some other students and faculty at Green Meadow High? How do Tracy’s feelings about Lily differ from her feelings about her own daughter? What do you think accounts for the friendliness between them?
10. Who is Larry Holleran, and why was he being considered for the Principal job? In your opinion, what theme or idea does Larry represent in this novel?
11. Many of the adult characters—in particular Tracy, Kyle, and Vito—are ambitious and deeply concerned with succeeding, both personally and professionally. What does success mean to the characters in this book? What does this novel have to say about the limitations of success as a primary motivation? Which, if any, of the adult characters do you feel is truly happy, and why?
12. By the end of the novel, has Tracy achieved her goals? What does she have to endure to receive the recognition she sought at the beginning of the novel? In your opinion, has Tracy “won”? Why, or why not?
Enhance Your Book Club
1. Curious about Tracy’s past? Read the Tom Perrotta’s novel Election to learn more about Tracy’s high school experience, which she grapples with in Tracy Flick Can’t Win.
2. Make your discussion of Tracy Flick Can’t Win into a book-to-screen night! Watch the cult classic movie adaptation of Election, starring Reese Witherspoon.
3. Looking for another satirical, compulsively readable novel set in high school? Pick up Curtis Sittenfeld’s Prep for your next book club meeting.
- Publisher: Scribner (June 7, 2022)
- Length: 272 pages
- ISBN13: 9781501144066
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Raves and Reviews
“Engrossing and mordantly funny."—People
"Even more piercing than its predecessor... With a lyric, polyphonic intensity, [Perrotta] poses a question to the class: What have we learned?”—The New York Times
"The verdict is in on Tracy Flick: we did her wrong."—The New Yorker
"Cleverly designed.... Perrotta has reclaimed the name Tracy Flick from the bucket of misogynist punchlines.”—Washington Post
"Perrotta catches up with Tracy as an adult, rescuing her from the fate of being used as an easy symbol of, well, anything. She’s much too complex for that."—Time
"Brilliant, biting satire... so lean and taut it almost reads like a screenplay."—Minneapolis Star Tribune
"[Tracy Flick is] a richly rounded character enduring a quintessential modern American struggle.”—Boston Globe
“Told with Perrotta’s piercing wit, wisdom, and exquisite insight into human folly, Tracy’s second act delivers acerbic insight about frustrated ambition.”—Esquire
"If you ever wondered what became of overachiever Tracy Flick... now you can find out in Tracy Flick Can’t Win."—Elle
"Perrotta [is] a specialist in suburban malaise.”—Slate
"Perrotta brings his trademark dark humor and insights into suburbia to the story, along with some sweet observations about friendship."—Real Simple
"Perrotta has what it takes to revisit the past without being predictable.”—The Atlantic
“Short chapters from many perspectives [will] keep readers alternately laughing and gasping.”—Los Angeles Times
"Humorous yet humane... prescient, darkly comical.”—San Francisco Chronicle
“Perrotta’s great gift is that he lets his love for his characters, flaws and all, shine through. . . . I was rooting hard for Tracy Flick to, finally, win.” —Seattle Times
"Sharp and perfectly executed…This is the rare sequel that lives up to the original.”—Publishers Weekly, starred review
"Smart, entertaining... The breeziness of the pacing provides tart counterpoint to weightier themes... which Perrotta handles with a deft but determined satiric touch.”—Booklist
“The plot unfolds with the you-are-there feel of a documentary, or mockumentary perhaps ... Nobody told this master of dark comedy there are things you can’t make jokes about. Watch him try.”—Kirkus
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