The Last Black King of the Kentucky Derby

By Crystal Hubbard
Illustrations by Robert McGuire

This book celebrates the life of Jimmy “Wink” Winkfield, a little-known sports hero. Born in 1882 to an African American sharecropping family in Kentucky, Jimmy grew up loving horses. The large, powerful animals inspired Jimmy to think big. Looking beyond his family’s farm, he longed for a life riding on action-packed racetracks around the world. As a teenager he began spending time at the local racetrack. He learned even more about horses, and studied the jockeys as well. Soon he was hired as an exercise rider, and by the time Jimmy was sixteen, he had been given a chance to ride as a jockey.

Like his hero, the great Isaac Murphy, Jimmy Winkfield would stop at nothing to make it as a jockey. He honed his skills in race after race. Although his path to success was wrought with obstacles both on the track and off, Wink faced each challenge with passion and a steadfast spirit. He won his first Kentucky Derby in 1901 and his second in 1902. After that, he continued to race for many years in the United States and Europe, until his retirement in 1930.

Horse racing, “the sport of kings,” enjoyed in Europe by royalty and the aristocracy, came to the shores of the United States with the earliest settlers. Races were recorded as early as 1665. At the time most horses of well-off landowners were cared for by enslaved men, so they were usually assigned to be jockeys. Through horse racing these jockeys gained fame and in some cases freedom. One such man, Austin Curtis, began racing as a teenager in the 1700s and became so well-known that he was considered America’s first professional athlete.

Horse racing’s popularity and prestige continued to grow with the nation. As African Americans gained freedom they continued to be part of horse racing as jockeys. On May 17, 1875, the Kentucky Derby—one of America’s oldest premier races—made its debut. Of the fifteen jockeys who raced that day, fourteen were black, including the winner, Oliver Lewis. Between 1875 and 1902 black jockeys won fifteen of twenty-eight Derbys, and African American Isaac Murphy became the first jockey ever to win back-to-back Derbys, in 1890 and 1891.

Barely five feet tall, Jimmy Winkfield became one of the household names of horse racing. Although he had more than 2,600 victories to his name, jockeying had its heartache for Jimmy as well. He faced discrimination from groups like the Ku Klux Klan and from white jockeys. Because of racism in the United States during the 1950s, Jimmy spent many years of his later life in Europe. Today Jimmy Winkfield is recognized as one of history’s greatest jockeys, the last African American ever to win the Kentucky Derby, and the jockey who came closest to winning three Kentucky Derbys in a row. He died in 1974 at the age of ninety-one. In 2004 he was inducted into the National Museum of Racing Hall of Fame in Saratoga Springs, New York. In 2005, Aqueduct Racetrack in Queens, New York, held the first running of the Jimmy Winkfield Stakes.

Teaching Tip
This is an excellent book to feature during your observance of Black History Month in February.

Before Reading
Prereading Focus Questions
Before introducing the book to students, you may wish to develop background information, tap prior knowledge, and promote anticipation with questions such as the following:

  1. Have you ever seen or ridden a horse? What is a horse like up close?
  2. Have you ever watched a horse race? What is atmosphere like?
  3. What does a jockey do? What special skills do you think a jockey needs to have to ride a racehorse?
  4. How do you expect to be treated by others? How do you try to treat other people? How do you feel if people don’t treat you well or fairly?

Exploring the Book
Write the title of the book on the chalkboard. Read the title aloud and discuss with students what the Kentucky Derby is. Then ask students what they think the title The Last Black King of the Kentucky Derby means. Invite students to comment on the illustration.

Page through the book, noting features such as the title page, dedications, Acknowledgments, Author’s Sources, Foreword, illustrations, and Afterword.

Setting a Purpose for Reading

Have students read to:

  • learn about what jockeys do
  • find out about determination in the face of discrimination
  • find out what Jimmy Winkfield did and why he is a sports hero

Write the following words and phrases from the book on the chalkboard. Read each aloud and talk about how it is used in relation to horse racing. Then have students write their own definition for each word and phrase and write a sentence that illustrates the meaning.

stable stable hand jockey silks snort
muzzle bolted pack winner's circle  
ablaze track astride neck and neck  
driving homestretch closing in rail  

After Reading
Discussion Questions
After students have read the book, use these or similar questions to generate discussion, enhance comprehension, and develop understanding of the content. Encourage students to refer back to the text and illustrations in the book to support their responses.

Literal Comprehension

  1. Where was Jimmy Winkfield born? What year was he born?
  2. On the first page of the story, what do we learn about Jimmy’s life and love of horses?
  3. When Jimmy was a boy, who was the rider that he aspired to be like?
  4. What did Jimmy learn during the time he was an exercise rider and a stable hand?
  5. Who was Bob May? How did he help Jimmy to become a jockey?
  6. What happened during Jimmy’s first race? What was his punishment?
  7. When did Jimmy win his first race? Where was he? What horse was he riding?
  8. Did Jimmy succeed in his third try at a Kentucky Derby win? What happened?
  9. Where did Jimmy go to race after he left the United States? When he retired, where did he live?

Extension/Higher Level Thinking

  1. What kinds of discrimination did Jimmy face throughout his life? Find passages in the book that describe incidents of discrimination.
  2. How did Jimmy feel after winning his first Kentucky Derby? What effect did this win have on his career?
  3. What was Jimmy’s strategy for selecting a horse to ride for the 1902 Kentucky Derby? Do you think what he did was fair? Why or why not?
  4. What do you think was going through Jimmy’s mind as he raced Alan-a-Dale around the track?
  5. What strategy did Jimmy use with his horse in his try for a third Kentucky Derby win? What do you think Jimmy learned from this experience?
  6. What drove the black jockeys out of horse racing in the United States?
  7. How do you think Jimmy felt when he returned to the United States after spending years in Europe? Why did he return to France to stay?
  8. What do you think the author means by the last line of the story: “The small boy from Kentucky had lived a big life”?

Literature Circles

  • The Passage Locator might look for the passages that illustrate what kind of person Jimmy was.
  • The Illustrator might research and create an illustration of different kinds of silks jockeys wear.
  • The Connector might find information about other famous jockeys either from the past or present.
  • The Investigator might find more information about the background of the Kentucky Derby.


Reader's Response

  1. What did you like or admire about Jimmy Winkfield? What didn’t you like or admire? Why?
  2. Can you relate to any parts of Jimmy Winkfield’s story or life? What parts? Why are these parts meaningful to you?
  3. How did Jimmy handle the discrimination he faced? What do you think made him so determined to go on?
  4. How does learning about the past help you understand the present?
  5. The Afterword tells about several injustices that Jimmy Winkfield had to deal with during his life. Identify an injustice you think is taking place today. Write an essay explaining what is wrong and how you think it can be changed.
  6. Read the quote from Jimmy Winkfield’s daughter that appears at the bottom of the Afterword page. How does the quote apply to Winkfield’s life? How does the quote apply to someone you know personally or to a well-known figure you know about?

ELL Teaching Strategies

  1. Assign ELL students to read the story aloud with strong English readers/speakers.
  2. Have each student write three questions about the story. Then let students pair up and discuss the answers to the questions.
    • Have students work in pairs to retell either the plot of the story or key details. Then ask students to write a short summary, synopsis, or opinion about what they have read.

Interdisciplinary Activities

Social Studies
Jimmy Winkfield’s parents were sharecroppers. Have students find out more about what sharecropping is, its origins, its history throughout the world, and its role in the economy of the southern United States from the end of the Civil War to the middle of the twentieth century.

Social Studies/Math
Explain to students that the Kentucky Derby is a horse race that is part of a three-race event called the Triple Crown of Thoroughbred Racing. Have students research the Triple Crown and compare the three races in chart or graph form. Students may record the following types of information: names of the races, names of the racetracks, locations of the racetracks, when the races are held, lengths of the tracks, track surfaces, winning horses, winning times. Students may also wish to include drawings or photos of some of the horses that have won the Triple Crown.


  1. Provide students with the winning times for ten to fifteen Kentucky Derby races and have students plot the dates and times on a line graph.
  2. Introduce students to the idea of split times. Working with one of the winning times for the Kentucky Derby, have students split the time evenly into five quarter-mile times (the race is 1-1/4 miles long). Then have them split the time unevenly into five quarter mile-times (e.g.: some quarters could take 10 seconds and others 20 seconds in order to add up to the winning time).

Language Arts

  1. Have students research one of the jockeys other than Jimmy Winkfield who are mentioned in the story and write a short biography about the rider. Or students may write a biography of any other jockey with whom they may be familiar.
  2. Challenge students to write a poem about a horse, a horse race, or some other event in The Last Black King of the Kentucky Derby. Encourage students to use some of the horse racing vocabulary they learned from this story.
  3. Ask students to write a newspaper article or a blog post about one of the races highlighted in the book. To make the article more personal, students might try creating fictional “quotes” of what some of the spectators, horse owners, and jockeys might have said.

Have students research aspects such as the origin, size, diet, life span, natural environment, and training of a few different breeds of horses. Students may wish to accompany their findings with images that illustrate the differences among the horses they have chosen to research.


  1. Have students create their own jockey silks using colored paper or cloth. Provide picture samples of current and past silks.
  2. Have students create a poster or an event program for one of Jimmy Winkfield’s Kentucky Derby races.

About the Author
Crystal Hubbard is a lifelong sports buff and full-time writer. In addition to The Last Black King of the Kentucky Derby, her children’s books for Lee & Low include Catching the Moon: The Story of a Young Girl’s Baseball Dream and Game, Set, Match, Champion Arthur Ashe. Hubbard lives in Missouri with her husband and their four children.

About the Illustrator
Robert McGuire is a full-time illustrator with a degree in fine arts. Much of his illustration work reflects his love of diverse cultures. He and his wife live in Astoria, New York. You can find him online at


About This Title

Guided Reading:




Interest Level:

Grades 1 - 6

Reading Level:

Grades 3 - 4


Animal/Biodiversity/Plant Adaptations, Nonfiction, Sports, Identity/Self Esteem/Confidence, Overcoming Obstacles, Occupations, History, Dreams & Aspirations, Discrimination, African/African American Interest, Biography/Memoir, Animals, Poverty, Sports History, Informational Text, Integrity/Honesty , People In Motion, Persistence/Grit, Self Control/Self Regulation, Pride


Fluent Dual Language , Fluent English, Biography and Memoir Grades 3-6, Appendix B Diverse Collection Grades 3-6, English Guided Reading Level R, Nonfiction Grades 3-6, Athletes and Sports, Black History Collection, Grades 7-12, High-Low Books for Preteens (Grades 4-6), African American English Collection Grades 3-6, Summer Olympics Collection, Appendix B Diverse Collection Middle School, Persistence and Determination Collection

African American Collection English 6PK


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