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The Desperado Who Stole Baseball bookcover

The Story behind the Story



and Parent Resources

for Desperado

Book II
in the
Cruz de la Cruz Saga

The Boy Who Saved Baseball bookcover



Teacher and Parent Resources
for The Desperado Who Stole Baseball
by John H. Ritter

Book I in the Cruz de la Cruz Saga
(Prequel to The Boy Who Saved Baseball)

"Fans of John H. Ritter's The Boy Who Saved Baseball have been waiting for this one… The field is set, the teams are aligned, but nothing is really as it seems… Ritter's use of vibrant imagery and musical phrases places this adventure right square in the annals of the oral Western tall tale—you'll want to read this one aloud, more than once." —Children's Literature Review

Research Topics before Reading Desperado:

Have students do Internet searches on:

  • gold mining methods; rank each method from least destructive to the environment to most destructive
  • Alfred E. “Fred” Coleman and the San Diego Gold Rush of 1870
  • 1880's star baseball player, Cap Anson, and his racial beliefs
  • racism and the economic justifications for it
  • the Negro Leagues
  • Moses Fleetwood Walker
  • Billy the Kid
  • William A. Hulbert and the 1880 Chicago White Stockings
  • the fate of the 1880 Cincinnati Reds

Have students write and discuss (before or after reading the novel) the answer to the question: Who profits from racism?

During Reading Activities for Desperado:

Keep a character log in which students draw a portrait or full-size picture of each character with his or her name, a thought bubble which includes a typical saying or thought of that character, a list of characteristics, personality traits, and how that character is related to other characters.

Use a timeline to track the events in the novel. Show dates, times, and places for each event. To enhance interest in the timeline, add illustrations for the more important events.

Have students write down and predict meanings of unusual vocabulary words, using context. They might then discuss those meanings in small groups and revise their definitions.

Themes to Consider when Reading Desperado:

  • Escape—Long John Dillon escaped from slavery with the Underground Railroad; Billy the Kid escaped multiple times from jail; Jack escapes from the tragedy of his past. Look for other examples of escape. Is a baseball game a form of escape? For whom? What about a horseback ride into the countryside?
  • Greed and corruption—Throughout the novel look for ways that decisions were made for reasons of greed. How many people benefitted from each decision? How can land be corrupted?
  • Treating land as a commodity—Consider the consequences both physically and spiritually to viewing land as a product to be manipulated for financial gain. Compare this to seeing the land as more valuable than the sum of its resources. What is the value of beauty?
  • Dreams—Dreams flavor this novel from beginning to end: a boy’s dreams, a Chicago baseball team owner’s dream to get richer, a desperado’s dream to settle down, Long John Dillon’s dream to have his players play baseball in the National League, and a town’s dream to live simply. What purpose does someone's dream really serve? What are your dreams? Have any past dreams come true? What is most important? Having a dream or following a dream or reading a dream? Can dreaming be dangerous? Can it be a "trap" from which a person might have to escape? Do you know anyone who has spent life as a dreamer—that is, without ever pursuing or reaching a dream?
  • Freedom—Being free is something our founders believed all Americans deserved according to our Declaration of Independence. Yet, African-Americans were considered only 3/5ths of a person in the U.S. Constitution. Notice that the main characters in the story (Billy the Kid, Jack, and Long John Dillon) have experienced various degrees of not being free. Are they free now? What constraints do they have? Consider skin color, age, being betrayed by the authorities. Baseball had a Reserve Clause that kept players bound to their home teams. How does that compare to slavery? Are people ever free? Do you feel free? What constraints are on you? Are these for a good reason? Are they just?
  • Secrets—Jack is full of secrets; some he's eager to divulge; some not so much. Compare his secrets to those of Marshal Danbridge, Vernon Toots, and William Hulbert. Why do we keep secrets?
  • Reading—Jack reads a newspaper clipping to Billy early on. What kind of reading does Billy teach to Jack? Consider Billy's "eyesight" challenge to Jack, reading other people, reading the land, reading a pitch.
  • Stealing—Jack describes the disease of diphtheria as having taken all three members of his family. He also claims to have "borrowed" a horse from the wagon train. Billy was supposed to be given freedom, but instead the governor stole his freedom by not keeping his word. Vernon Toots was stealing the best players on the Dillontown Nine (Lil Lou and Shadowfox Coe). Stealing a base is an honest play in baseball, but in the big game King Kelly literally stole past second base. At the end of the novel Billy steals home (with Jack as an accomplice). In baseball and in life, what motivates people to steal?
  • Sacrifice—Baseball has a sacrifice play in which the batter commits to giving himself up as an easy out in order to advance a runner who is already on base. John Dillon has seen the beauty of the land sacrificed for riches. Jack sacrifices the truth in order to ease his pain. What sacrifices do any of the other characters make? How does Eliza sacrifice herself to save Billy?

Discussion Questions during Reading of Desperado:

Ch. 1 & 2:

  • Describe the landscape in Chapter 1. What clues, given in the way the characters talk and dress, make you believe this story takes place in 1881?
  • What adjectives would you use to describe Jack? Find a sentence or two in the first two chapters that you think reveals who he is and tell why.
  • What kind of person is Henry? What do you know about him from his encounter with Jack on the trail? Back up your opinion with quotes from the book.
  • On page 16, Henry tells Jack, “You, son, have an imagination that knows no fear.”  Is there a character in The Boy Who Saved Baseball who is like Jack? Why is imagination so important for Jack, or for Tom in The Boy Who Saved Baseball? What purpose does the imagination serve for each boy?
  • Vocabulary: scandalize (p. 9), woo-haw (p. 12), baseball moon (p. 15), home stone (p. 15), malarkey (p. 15), desperado (p. 2)

Ch. 3 & 4:

  • Why doesn’t Jack tell the truth? What do you think he’s hiding?
  • What did you learn about Jack by how he escaped from the shooter?
  • If you were in Jack’s shoes, how would you feel and how would you react to learning that Henry was really Billy the Kid? What advice would you give Jack now?
  • Vocabulary:  bluff (p. 18), josh (p. 21), gloamy (p. 22), stoic (p. 25), shenanigans (p. 26)

Ch. 5:

  • Why did the author switch to a different setting—both in place and in time—at this point in the novel?
  • Who is Vernon Toots? The author compares him to “a factory rat.” How are his actions like a rat? Why did the author use the word "factory"?
  • Who is William Hulbert? What does his office tell you about him?
  • On page 30, Hulbert buys “a thousand shares of Pacific Railroad.” Why would that have been a good investment at that time? How much of a gambler would you consider Mr. Hulbert to be?
  • Vocabulary:  gauntlet (p. 29), cryptic (p. 30)

Ch. 6:

  • Billy asks Jack what’s “so attractive about baseball” that he’d go 1500 miles to get a chance to play. What are the reasons Jack considers telling Billy, and what does he finally tell him? What ideas does Jack have for changing the game of baseball “well into the future”? What does this attitude reveal about his personality?
  • How is the relationship between Billy and Jack changing?
  • Vocabulary: perused (p. 33), knoll (p. 34), concoctionary (p. 37), citified (p. 37)


  • What does the message on the telegram say? What does it mean? What do you think will happen next?

Ch. 7:

  • In the last chapter, Billy tells Jack he knows about box canyons because he reads the land (p. 34). In this chapter, Billy advises Jack to “read the mountain” in order to figure out the best trail to use to climb up the mountain. What does Billy mean? What other things would it be important for a desperado to “read”?
  • Jack and Billy run into an old-timer who says that John Dillon “stopped all sluicing, except by pick or chisel and a puddling tub.” (p. 43) Research sluicing techniques, and then hypothesize why John Dillon would restrict the techniques for acquiring gold.
  • What does the line, “We’re not in Kansas City anymore” (p. 47) mean?
  • Vocabulary: brackish (p. 42), sluicing (p. 43), baseball joe (p. 46)

Ch. 8 & 9:

  • How could it be possible that Jack would not have known his uncle was African-American? What kind of problem does this pose for Jack?
  • At the end of Chapter 8, a man in a crumpled white suit appears. What significance do you think he might have here? Who might he be?
  • Certain events in these two chapters seem nearly impossible. What are the characteristics of a tall tale? Does this book meet those criteria?
  • Vocabulary: smithereens (p. 49), agile (p. 49), home stone (p. 51), agape (p. 52), coddle (p. 57)

Ch. 10 & 11:

  • This chapter begins with a change in the author’s voice. Who is the narrator now? Why did the author insert this section?
  • Billy tells Jack that he knows when Jack’s bluffing because Billy can “read” him. Billy calls a certain mannerism a “tell.” How do Billy’s ways of reading people and reading the geography help him survive as an outlaw?
  • What kind of sheriff is Danbridge? What are his motives? Consider the way he entered the game to arrest Coe. What adjective would you use to describe him?
  • Vocabulary: squibber (p. 67), gaggle (p. 71)

Ch. 12 & 13:

  • On page 75, Eliza explains to Jack that Dillontown is having “a war of dreams.” Consider that notion. What are the two warring sides dreaming about? It seems every main character in this book has dreams for the future. What purpose do dreams serve? What are your dreams? Have any come true?
  • Long John Dillon explains why he wants to keep Dillontown the way it is, free from invaders. He says, “I either slow down the destruction of these hills, the poisoning of these rivers and streams, and establish Dillontown as a year-round baseball heaven full of grazing land, apple trees, and ballparks, or I give up and move on myself.” (p. 86) How does this idea compare with the ideas of modern day environmentalists?
  • John Dillon tells Jack that, as a runaway slave, he was aided in his run for freedom by the Underground Railroad and protected by a Quaker family in Iowa. How would you suppose that John Dillon's personal history influenced his decision to forgo tearing down the mountain in order to extract more gold versus being content with what he had, including the natural beauty of the town?
  • Vocabulary: drover (p. 77), sconce (p. 83), perused (p. 84), gumption (p. 84)

Ch. 14 & 15:

  • Why do you think Billy is a good poker player?
  • Regarding the second telegram, notice that it, along with the previous telegram, was delivered and received earlier in time. What do these messages reveal about the Chicago White Stockings’ owner? Is the author's placement of these messages meant to ambush you, the reader, too?
  • Notice that Billy, Jack, and Long John Dillon all have secrets. And now Jack is making Eliza keep a secret. What do secrets have to do with this novel? Why do so many people have secrets? Is this human nature?
  • How could “secret knowledge” come to someone (such as Jack) in a dream?

Ch. 16 & 17:

  • Jack learns the true story about Billy. How is his story similar to Long John Dillon’s?
  • When people “keep to ‘emselves,” Billy tells Jack, it let’s a man feel free to be himself. Is that true for you? Or do you feel more free when people are around, such as when they offer care and support?
  • What are the benefits of “hiding in plain sight”?
  • Vocabulary: “on the dodge” (p. 111)

Ch. 18, 19, & 20:

  • To be “locked on” in baseball has a certain meaning. Are there other sports when this moment occurs—football, basketball, soccer? What about in life? What times have you been locked on to something? What did it do for you? What was it like?
  • On page 118, the opening section implies that only angels can arrange those magic moments in life like being “locked on.” Why might the author introduce this idea? For what reason might angels be around for the three orphans, Jack, Billy, and John?
  • When Hulbert asks for a lawman to be the stakeholder for the money being wagered, Long John Dillon says the umpire will be the stakeholder. What does that tell you about the laws of the town?
  • Vocabulary: raucous (p. 131)

Ch. 21, 22, & 23:

  • The Dillontown Nine go to “church,” but Jack learns that, for them, church is the gold mine with baseball paraphernalia all around. After surveying it, Jack says, “This is the holiest place on earth.” (p. 145). How is the gold mine like a church? In what ways might this meeting place improve the morals and values of the men who congregate inside?
  • After Uncle John explains the truth about his wager with Hulbert, the team is horrified. What is really at stake?
  • When Jack was put on the spot by the prophet Blackjack Buck to share some of his “secrets of baseball,” Jack spoke of baseball plays that had not been introduced to baseball yet. Can you think of a deeper meaning to the “secrets” of baseball? If so, what is it?
  • Vocabulary: doffed (p. 138), donned (p. 138)

Ch. 24:

  • Compare and contrast what is happening regarding the power struggles within the Chicago team (especially between Hulbert and Cap Anson) and those within the Dillontown Nine.
  • On page 159, Hulbert says, “Baseball is business, plain and simple.” Here, he was referring to the ability to keep baseball players on a team using the Reserve Clause. In 1975 the players were able to get rid of the Reserve Clause and they could market themselves to the highest bidder. As a result, some players have gotten huge salaries after leaving their “home” teams. Do you like the way baseball is going, with players leaving or being traded often, and with few, if any, star players staying for more than a few years? In your opinion, what would be the fairest way to run baseball for the fans and the players?
  • Did Hulbert really impose a secret ban on black men playing major league baseball? How? And why?
  • Chapter 24 ends with this: “Knock ‘em down, kick ‘em around, and don’t let ‘em know what hit ‘em,” said Hulbert. “That’s my philosophy, in business and in life, and it has never failed me yet.” (p. 162). What do you think about this philosophy? Does it work?
  • Vocabulary: galoots (p. 161)

Ch. 25 & 26:

  • When the team questioned Billy’s identity, Dixie claimed he “knew a John Henry, down south.” Jack tried to cover for Billy when the team suspected him by saying that “Everyone knows Billy the Kid stands six foot six and weighs about two forty-five.” (p. 165) Who was “John Henry” in folk tales? How does he fit in with the novel? And who was 6 foot 6 and weighed 245? (Find the lyrics to the song “Big John.”) How does Big John fit in with this story?
  • On page 168, the wind is coming in from the east, and there’s a baseball moon. What other John H. Ritter books do these two ideas suggest? What do these conditions foretell?

Ch. 27-30:

  • Uncle John says, “And my people, we always side with the underdog.” (p. 186) Who are the underdogs in this novel? For what reasons might minority ethnic groups be considered underdogs? Why root for them?
  • Interesting that a key technique to getting good at baseball is having a good enough eye to shoot silver dollars—in other words, to put a hole in money. Symbolically or metaphorically (even if this is true), how does this idea tie in to other themes in the book, such as greed and seeing land as a commodity, and the opposite idea that people can live generously and still be in harmony with the land?
  • On the night before the game, Jack thinks up the suicide squeeze play which involves “stealing home.” How could stealing home be a metaphor for a bigger idea in this book?
  • In telling a story about the first time he played professional ball, Uncle John says, “That’s the beautiful thing about baseball. The fairness.” Is baseball always fair? Why would the author have Uncle John say this?
  • In Chapters 29 and 30, Jack, Billy, and Uncle John all share stories about their brothers and missing them. How does this fact make it more believable that Long John Dillon might accept Jack as a possible nephew and Billy as a friend? How does a sense of “brotherhood” run through the book? Can brotherhood and racism coexist?
  • Vocabulary: popskull (p. 173), umbrage (p. 176)

Ch. 31-35:

  • On page 206, the Chicago White Stockings are described as having a uniform that conjures up “the image of a ruthless band of outlaws working for a desperado king.” Who are the real desperados in this story?
  • A red-tailed hawk flies overhead and gets caught in the thermal updraft. Warm air is rising. Winds are changing. How does wind affect the story? Why does the hawk appear here?
  • How is baseball “a way to give thanks to the Creator” as Jack seems to be thinking (p. 224)?
  • Vocabulary: deluge (p. 227)

Ch. 36-41:

  • How is a baseball game like the “story of a lifetime”?
  • In Chapter 33, there was a sacrifice bunt by Long John Dillon. In Chapter 37, more sacrifices. How is sacrifice a necessary part of a baseball game—or of a lifetime?
  • In Ch. 40, why is leaving the town not an option? How might the words of the song “Amazing Grace” speak to Dixie Bodine about slavery and his old belief system?
  • What does Uncle John mean when he explains the saying, “the best things in life are free”? Why would freedom mean so much to him? To Billy? To Jack?

Ch. 42 & Author's Note:

  • Did any of the facts in the Author’s Note surprise you? In what way?

Activities and Discussion Topics after Reading Desperado:

  • Now that you’ve finished reading the book, go back to the quote on page 2 (below). Think about what they say in Dillontown, now that you’ve gotten to know Billy the Kid. Write an obituary for him from the perspective of a citizen in Dillontown.

    …Riding along that westward trail came some wild and cagey hombres, including none other than one William H. McCarty Antrim Bonney, erstwhile known as Billy the Kid—the cold-blooded killingest, back-stabbing stealingest, double-crossing, double-dealingest desperado on the sundown side of the Mississipp’. Or so folks say.
    In Dillontown, we say something else. (p. 2)

  • The author uses unusual names for members of the Dillontown Nine, such as Long John Dillon, Shadowfox Coe, Blackjack Buck, Fence Post Hayes, Little Lou Montegue, etc. What do these names tell you about the genre of the book? About each of these characters?
  • People are not always as they appear. Some are called outlaws, like Billy the Kid. Others are outlawish in their actions or thoughts. Name three characters who can be considered both outlaws and law-abiding citizens. Support your stance with examples from the text. Then consider why Mr. Ritter created characters with hidden agendas. How does that change your thinking about them as you read?
  • In Chapter 34, baseball is described as a game played in many forms such as lacrosse by Native American tribes for reasons which include resolving conflicts and “as a way to give thanks to the Creator.” How do the events in this book show that baseball is indeed capable of resolving conflicts, and how might a modern day baseball game be “a way to give thanks to the Creator”?
  • Have a class debate on treating the land as a product (such as Hulbert wanted to do with strip mining) versus using the land in its more natural state. Students may then choose to write a persuasive essay, supporting their stance with events from The Desperado Who Stole Baseball as well as evidence from their own experience with growing communities.

Symbolism and Metaphor as Foreshadowing Tools in Desperado:

  • In the book, red-tailed hawks appear at various times, such as on pages 4, 36, 60, and 219. Under what circumstances do these hawks appear? What meaning might they have in Jack’s life? What meaning do they have in The Boy Who Saved Baseball?
  • When Henry asked if Jack knew who he was (p. 6), Mr. Ritter wrote, “The boy shook his head, but the very question planted a wildpatch of worry in the fertile fields of his mind.” Why did the author describe Jack’s concern using the metaphor of “fertile fields”? How does that idea reflect the setting of Desperado? How is it echoed in the rest of the book? What metaphor would you use to describe how one of your worries or concerns might grow?
  • On page 7, Billy uses the phrase, “The truth has set you free.” How is this idea used throughout the novel? (Consider Long John Dillon’s speech in the cave.)

Lesson Plans for Desperado contributed by Cheryl Ritter, San Diego Area Writing Project fellow
and Explorer Elementary Charter School teacher.

Geometric Character Analysis with Desperado:

This is a very engaging activity! By using geometric or abstract shapes, students represent characters and themselves as readers and arrange the shapes on paper to suggest a graphic interpretation of character personalities and conflicts and the reader’s response. This activity can be done after reading a short story or novel with complex characters. Here's how:

1.   After reading, introduce the activity by drawing several geometric or abstract figures on the board (circle, triangle, rectangle, square, blob).  Ask students what type of personality each shape suggests to them and list their answers.  (Answers will vary—that’s good!)

2.   Next, list all the characters in the text with the whole class.

3.   Have students then choose 3 of those characters—main and subordinate—and along the side of a blank piece of paper, create shapes to represent them.  The shapes should be abstract, not the shapes of known objects, and students should have reasons based on evidence from the text for each shape.  Students write the names under each shape.

4.   Students also create a shape for themselves as a reader to show how they interacted with and responded to the actions of the characters in the story.  They write “Reader” under that shape.

5.   Next ask students to arrange the character and reader shapes on the paper in such a way that their placement and size show how the characters relate to one another and how the reader responded to the characters’ actions.  Students may draw a symbolic frame around the characters and reader, perhaps related to themes in the text.

6.   Ask several students to share this draft of their diagrams with the class and to explain their shapes, explaining reasons for the shape, placement, and size.

7.   Now introduce colors, asking students to think about what they symbolically represent.  Students can now create a final version of their diagram, adding color by using either colored pencils or by cutting the shapes from colored construction paper.  The medium of using paper, and cutting and manipulating shapes, brings another dimension to their thought process.  They can also use arrows, dotted or jagged lines, and vary shades to better explain relationships.

8.   After all are finished, have them explain their final diagrams to each other in small groups.

9.   Have students write an essay that includes an introduction, supporting evidence, and a conclusion. Choose at least one of the characters, along with the “Reader” shape, and describe their shape, size, placement, and color in the diagram. Justify their interpretation using specific details or passages from the text.

Geometric Character Analysis contributed by Cheryl Ritter, San Diego Area Writing Project, adapted from original activity created by David Partenheimer, Missouri College professor.


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