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About The Book

In the eighth book in the New York Times bestselling middle grade series inspired by the life of iconic New York Yankee Derek Jeter, young Derek and his friends learn how to balance competitive spirits with their love of the game.

As Derek and his team tackle playoffs, everyone deals with the pressure in different ways. And practice gets intense! One of Derek’s teammates, Avery, starts being especially hard on herself. She isn’t even enjoying the game anymore. Can Derek and the rest of the team pull her out of her funk?

Inspired by Derek Jeter’s childhood, this is the eighth book in Jeter Publishing’s New York Times bestselling middle grade baseball series that focuses on key life lessons from Derek Jeter’s Turn 2 Foundation.

Reading Group Guide

Reading Group Guide

Wind Up

By Derek Jeter with Paul Mantell​

Prereading Assignment

Review “Derek Jeter’s Ten Life Lessons.” They are listed in the front of the book.

Discussion Questions

Chapter 1—Make-or-Break
Derek Jeter and his team were pumped for the season’s last game before the playoffs. It was the final crossroads. If they won, they would go to the playoffs; but if they lost, the season would be over!

After a great start, Avery was having trouble with her pitching control. She threw a high fastball, and the batter nailed it to center field, but Mason, the Yankees’ capable team fielder, ran “. . . back, back, back and made a ‘snow-cone catch’ to save that pitch from a probable homerun.”

Define snow-cone catch. Using a search engine, list at least three outfielders famous for their snow-cone catches.

Chapter 2—Stress Test

It was the time of year when Jeter’s school was planning for the class finals and the statewide standardized testing. Emotions were high, particularly since the baseball playoffs were so close. The pressure was on! Classmate Gary Parnell, Jeter’s nemesis, made the time tense and even more complicated by his humiliating end-of-the-school-year challenge for Derek.

Do you think that Gary Parnell, Derek’s nemesis, is a braggart or bully, or both? Define the words and please explain your choice.

Jeter is known as one of the smartest kids in school, but standardized tests had him worried. He shared his concerns with Vijay, one of his best friends. Vijay promised to help him study for the upcoming exams.

What is test anxiety? Explain why partner-prepping is a good practice.

Chapter 3—Serious Business

Playing shortstop during a practice on Jeter Hill, Derek took a dive for a speeding ground ball and skidded on a rough patch of dirt, skinning his chest and legs. Later, at home, Derek winced and cried out in pain when his mom tried to treat his injuries. After treating his wounds, Derek’s mom had a serious conversation with him about working himself too hard, reminding him that “‘no matter what happens, it’s still a game.’”

Explain in your own words what you think she meant.

Yankee teammates Avery, Derek, and Peter were all too emotional, much too wound up, and absolutely too tight to play their best, resulting in mistakes, injury, and bad behavior—on the field and off.

If you were one of their coaches or parents, what would you recommend to the young players to improve their game?

Chapter 4—Earthquake

Dave finally told Derek the sad news that he was moving away.

The disappointment of moving or having a close friend move away can be emotionally traumatic.

In writing, briefly share an experience you’ve had when someone you know had to leave your school or neighborhood; or perhaps you were the one who had to pack up and leave your familiar surroundings for the unknown. Pick either scenario to explain what you were feeling. Try to include positive emotions or outcomes that came from the change, even if it felt negative at the time.

Chapter 5—End of the Line?

Sometimes, several things can happen all at once which can negatively affect your mood or behavior. These combined situations may cause you to feel sad or frustrated. Feelings of hopelessness can produce nervous energy and worry. For Derek, Parnell’s constant needling about the end-of-the-year finals challenge, his best friend Dave’s news about moving away at the end of the school year, and the anxiety about the pending baseball playoff game against a rival team have combined to make Derek agitated and “off his game.”

Please describe what it means to be “off your game” in your own words. Explain what you would do in a situation like this. What advice would you offer Derek to help him get through each of the situations described above?

Discuss in a small group, or with a friend, a difficult experience with a sibling or classmate in which you have had to decide how to handle and resolve a dilemma. What were the issues, and how were they resolved? Did you need to get someone else involved, like a teacher or parent? What did they do to help?

Chapter 6—Playoff Fever

Avery is the only girl on the Yankees Little League team, but she has been recognized as a pretty good pitcher. Now, in the playoffs, she feels the pressure to come through for the team. However, with all the playoffs anxiety, it seems that Avery may be getting sick.

Read chapter 6 out loud. Derek senses that Avery’s pitching may be getting a little out of control or that the rival team may be able to predict her strategies. He speaks to her on the mound, suggesting an unusual and innovative pitching ploy. What advice did Derek offer, and what was the result?

Avery’s mom also seemed troubled about the mental and emotional pain that Avery was experiencing and how it was affecting her game. After the game, her mom offered an encouraging hug.

What advice do you think was given? How would you comfort or advise a friend you noticed going through a tough time?

Chapter 7Confidence and Doubt

Coach Jeter, Derek’s father, is coaching Derek’s little sister Sharlee’s team this season, and Sharlee is overjoyed with exuberance and confidence. She never doubts that her team will win a game, even though the possibility does exist. In this chapter, Coach Jeter corrects Sharlee when she exclaims that she hit a “suicide fly.”

What is a sacrifice fly and a suicide hit? Define each term and use them in a sentence.

Although Derek is consumed with test anxiety, allowing his nemesis, Gary Parnell, to unnerve him each school day, Derek knows he has a great friend in Vijay, who has promised to help him prepare for the upcoming standardized tests.

What testing tips did Vijay give Derek? Why do you think the ideas could be helpful? Discuss a time that you were nervous about a test, and how you studied and calmed your nerves.

Chapter 8Avery’s Quest

Both Avery and Derek are consumed with anxiety and worry, and each is a little sad for different reasons. Think for a moment about what makes you feel the same way.

What specific issues are affecting Avery, and what makes Derek feel so unnerved? Compare their emotions and how their actions show others what they’re feeling.

When you or a close friend seem to be in turmoil, it’s a good practice to seek advice from an adult you trust, perhaps a parent, coach, or a supportive teacher.

Derek reached out to his father and former Little League coach when he was unable to resolve his own anxiety or help Avery with the issues she was experiencing. What advice did Coach Jeter offer? Why do you believe it was helpful?

Chapter 9Giant Killers?

Derek paid attention to the batting habits of the Giants, who were acting like super confident League leaders. What did Jeter suggest to Harry, the Yankees’ pitcher, which gave the team the break they needed to level the playing field?

Jeter knew that the Giants were the best hitting team in the league that season. So he was counting and hoping for a little magic from the Yankees’ pitching mound. What kind of magic was Derek able to pull off that the coach claimed excitedly was “‘the play of the day’”?

Why would it be a good thing to be labeled the underdog in a competitive situation?

Chapter 10Fight for Survival

As an underdog, Derek knew that the Yankees’ only chance to win against the League-leading Giants was to be prepared.

Ultimate Fighting Champion kickboxer and former UFC Women’s Strawweight Champion Joanna Jedrzejczyk has said, “You can be an underdog, but you can beat the champion.” Derek encouraged Avery to come early to the game so they could practice their infield and double play strategies. What was the result of their pregame practice? Discuss the above quote from Jedrzejczyk.

“Practice makes perfect” is another well-known motivational phrase.

Select another famous quote or saying that you know, and research its origin. In a small group, discuss your choice and share a personal experience related to your selection.

Chapter 11—Dave

The math and science finals were over, and the English essay and the standardized testing would soon be completed. It was time for Derek to relax and enjoy the process. But Gary Parnell, Derek’s classmate and nemesis, would not let him forget the challenge. What would the outcome be? Discuss both options—Derek’s loss versus Gary’s loss.

Reread chapter 11. Carefully review the essay handwritten by Jeter for his English final, “An Important Lesson I Have Learned.”

What was the “lesson learned” specifically in Derek’s English essay? Why do you think it was important for him to write down exactly what he was feeling? Explain your observation.

Chapter 12—Crash and Burn

After an undefeated season, Sharlee’s baseball team plays their last game. Sharlee was up to bat with two runners already on base. Her solid hit drove both base runners home, but Sharlee was tagged out when she tried to run all the way home herself. She was upset for the moment but began to celebrate the “obvious” game win a little too early. Sadly, the game was not over. The opposing team rallied and won the game, reminding them all about the now-familiar quote “It ain’t over till it’s over,” uttered by Yogi Berra, American baseball legend, during a National League pennant race.

Explain what Yogi Berra’s quote means, and how it’s meant to make people behave.

In what year did Mr. Berra make this offbeat quote? How does this “Yogi-ism” apply to Sharlee’s situation, and to Derek’s situations both on and off the baseball field?

Avery is very sick. Her doctor has diagnosed her upset stomach as severe gastritis. He recommends a break from baseball! The tension is affecting her physical health. Therefore, Avery’s mom, Mrs. Mullins, is pulling her out of the Little League Championship game scheduled for Saturday.

Derek is very worried about his friend and concerned about how the team will do without Avery. Share an experience when you or a family member had to miss an important event due to an illness or prior commitment and discuss how it made you feel. Be specific.

Chapter 13—Boiling Point

In an uncomfortable conversation about test scores, Gary Parnell claims that the standardized tests measure aptitude, not hard work.

Explain or define the meaning of aptitude, and discuss its relationship to an individual’s IQ. Is IQ level an important factor in aptitude development? Defend your answer.

In a group study, the night before the exams, Derek, Dave, and Vijay all study together for the standardized tests. They discover that the reading comprehension sections often offer confusing multiple-choice options.

What is the best test tip in selecting the most correct response?

Chapter 14—Back in the Game

Avery was bound and determined to play in the championship game, no matter how she felt or what her mom or the doctor recommended.

What do you think about Avery’s decision? Review her motivation to play in the game anyway. What would you have done if you were facing the same situation? Outline the pros and cons of Avery playing versus sitting on the sidelines.

Also facing game-day anxiety, Derek asked his father to help him practice his infield shortstop techniques just before the game began. He wanted to warm up, remembering that “Practice makes perfect.”

Did the extra practice help or hinder Derek’s performance? What was the outcome? Discuss why too much practice or study might have the opposite effect of what we want to happen.

Chapter 15—Reaching for Glory

Up to bat, Avery was not afraid to face Brad, the Tigers pitching marvel. However, after nearly getting hit at the plate, Avery was thrilled to nail a fastball straight past the obnoxious pitcher that “sizzled” into center field!

What would have happened if Avery had chosen to stay home instead of playing in the big game? Discuss what you would have done in Avery’s position and examine any alternative options you might have chosen instead.

Chapter 16—Fight to the Finish

The Little League Championship has begun. The tension is high with both teams ready to do their best. After a few innings, the game remains scoreless, but the Tigers pull ahead to score first.

Although the Tigers scored first, what maneuvers by the Yankees kept the game fierce and competitive? Be specific. How did the Yankees’ actions demonstrate teamwork and cooperation?

Mr. Rick Russell, Brad’s father and the Tigers’ coach, spoke to Derek after the game. Mr. Russell was impressed with Jeter’s work ethic and game dedication. Despite the game’s outcome, Russell asked Jeter to consider trying out for a spot on the Little League Traveling Team in the fall. Jeter was elated.

What do you think it was about Derek that caught the eye and interest of the Little League scout? What specific behavior by Derek did Mr. Russell observe?

Chapter 17—End of the Season

End of the season, end of the school year, and sadly, it may be the end of a great friendship. One of Jeter’s best friends, Dave, is moving to Hong Kong. They promise to write and stay in touch, but will they? On the other hand, Derek is a little distracted from all the doom and gloom of the championship loss and friend’s move, by his own bit of good news.

Derek has several issues to be sad about, but there are also things that he can be happy about. Make a list of at least five positive things that Jeter has to look forward to in the future.

Earlier in the book, Derek’s dad Coach Jeter offered a bit of comforting advice “‘You’ve got to be able to enjoy the ride, win or lose . . . ’”

In what ways can you apply this important principle to issues in your own life? Compose your thoughts and share in a classroom small group setting.

Extension Activities

The Road Not Taken, a Poetic Reading Exercise

Part One: The instructor will read “The Road Not Taken” by Robert Frost to the entire class and entertain any comments about the poem. The class will break up into smaller groups to discuss the poem further, including what they believe is happening in the poem, the piece’s tone, and how they feel about the speaker’s final choice. This group exercise is an opportunity to explore personal choices and recognize moments of important decisions. Encourage students to talk about decisions they’ve made, and the outcomes that came from it.

Part Two: Ask students to use a search engine to discover important facts about the life of the poet Robert Frost. Select a different poem by Frost to read aloud in a small group setting. Discuss and compare the two choices.

If time and resources permit, plan an in-class video showing of “The Road Not Taken” by Robert Frost. Compare adaptations and discuss. Some examples of recordings are those featuring actor Tom Hiddleston or pastor Ezra Tillman, and an animated version by TED-Ed, among many others.

Let’s Stay in Touch: A creative letter-writing exercise
Compose Derek’s first letter to Dave, who is moving away from Kalamazoo at the end of the school year. Use Derek’s own voice, or else create your own letter to a friend who has moved away but with whom you want to stay in touch.

An Important Lesson I Have Learned: Essay Writing Practice

Read Derek’s essay in chapter eleven.

Option 1: Draft your own essay entitled “An Important Lesson I Have Learned.”

Option 2: Create your own essay entitled “When I Had to Say Goodbye.” (Suggested subject(s) could be about a pet, sibling, or grandparent who has passed on or moved away.)

Wind Up guide written in 2021 by Chrystal Carr Jeter, Children’s Literature Consultant, formerly of Willoughby-Eastlake Public Library, Willoughby Hills, Ohio.

This guide has been provided by Simon & Schuster for classroom, library, and reading group use. It may be reproduced in its entirety or excerpted for these purposes. For more Simon & Schuster guides and classroom materials, please visit or

About The Author

Maureen Cavanagh/Jeter Publishing

Derek Jeter is a fourteen-time All-Star and five-time World Series winner who played for one team—the storied New York Yankees—for all twenty seasons of his major league career. His grace and class on and off the field have made him an icon and role model far beyond the world of baseball.

Product Details

  • Publisher: Simon & Schuster/Paula Wiseman Books (April 13, 2021)
  • Length: 192 pages
  • ISBN13: 9781534480452
  • Grades: 3 - 7
  • Ages: 8 - 12

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