As with nearly any period in American history, the Progressive Era offers its share of contradictions. In the arena of race, the country, that is to say the white-majority portion of it, tired quickly and thoroughly of the radical measures of Reconstruction (1865–77), which officially ended slavery and at least theoretically made blacks full citizens. During the Age of Reform, as the Progressive Era is often called, the United States largely reversed the gains of Reconstruction, constitutionally sanctioned racial segregation (in Plessy v. Ferguson, 1896), and ignored the rising tide of savage lynchings across the South, which reached a crescendo in the late 1890s and early 1900s as hundreds of blacks were murdered without trial, often without even a formal declaration of charges. Whites in the South disenfranchised blacks, limited their education, and held them in virtual peonage as sharecroppers and domestic servants. If, during the Progressive Era, there was great ferment in the United States about social justice and the social gospel of Christianity, the excessive power and influence of the merchant princes and of corporate business, the condition of urban slums and of persecuted immigrants, the victimization of young women lured into prostitution, and the terrible impact of alcohol on the working man, none of this concern carried over to blacks, who were told to sink or swim. Indeed, in this Social Darwinist age, many white thinkers about race believed African Americans, unable to compete, would die out.

On the other hand, during this period, African Americans began to build their own institutions, notably churches and church-based organizations, fraternities and sororities, and schools like the Tuskegee Institute. Political and reformist organizations like the National Association for the Advancement of Colored People and the National Urban League were started (mostly by liberal whites). Blacks formed a small but important class of educated leaders that included W. E. B. DuBois, William Monroe Trotter, Ida B. Wells, and Booker T. Washington. And most remarkably, blacks began to have a presence in and an impact on American popular culture, which was beginning to become around the turn of the century much the way we understand it today: leisure entertainment for the masses revolving around movies, theater, music, and sports. It was especially in the realms of music and sports—both of which were becoming highly professionalized and intricately connected to the ever-increasing urbanization of the nation—that blacks were significant, far out of proportion to their numbers. There were ragtime, "coon songs" that morphed into the Broadway song, early jazz, and new forms of social dancing. And there were sports played by both whites and blacks, like boxing, baseball, race walking, bicycling, college football and basketball, and, finally, horse racing.

Joe Drape's Black Maestro: The Epic Life of an American Legend is the biography of a black jockey named Jimmy Winkfield, who was born in 1882, four years after the first black heavyweight champion, Jack Johnson, a far more influential and famous athlete. He shared with Johnson the fact that he was born into a generation that had no firsthand experience of slavery, a generation white southerners of the day called New Negroes, a potentially troublesome lot. Winkfield was born in Chilesburg, Kentucky, in the heart of Bluegrass Country, the youngest of seventeen children. His parents died when he was very young, although the causes and even the dates of their deaths are unclear. Drape tells us Jimmy "was alone. . . . [He] was estranged from his siblings." So, as we are told, "he orphaned himself" to horses. Why he wasn't reared by his siblings and why they were estranged is uncertain. Like Topsy, one supposes, he just grew. The difficulty of reconstructing Winkfield's childhood and familial relationships is part of the problem with this biography; Winkfield seems, in many respects, an impenetrable subject, much more so than some of his black contemporaries like Johnson and bicyclist Major Taylor.

Winkfield hung around the racetracks and was enveloped in a black, masculine world of stable boys, groomers, and jockeys, a sort of professional subculture in the larger subculture of white owners, trainers, jockeys, and bettors who made up this highly competitive, rough-and-tumble, boom-or-bust world, a world where, as Drape puts it, blacks and whites interacted easily, "rubbed shoulders without cross words." Horse racing was a major sport in America at the time, drawing huge crowds. Until the late nineteenth century, black jockeys dominated the sport, including stars like Isaac Murphy and Willie Sims. These people became heroes to the young Winkfield and the other working-class black boys who hung around the stables, boys who had never heard of DuBois and only vaguely knew the name of Washington. This was the underbelly of DuBois's Talented Tenth, the class of people the Tenth was supposed to lead, but one supposes the black boys and men of the racing world were exemplars of Washington's vision of blacks taking advantage of being in the South and doing manual work, of casting down one's bucket where one was, although Washington had little use for popular culture.

Winkfield began riding as a teenager and soon developed into a first-rate jockey, indeed, an extraordinary one with a great feel for horses. He traveled the thoroughbred circuit, which included New Orleans, Chicago, and Saratoga Springs, NY. It was in the North that he faced his greatest difficulty, as the white jockeys, particularly the Irish, moved violently and relentlessly to kick blacks off the horses. Race wars were fought on the tracks, sometimes resulting in serious injury. In this instance, it was the white southerners who were forced to acquiesce to the demands of the northern white jockeys and horse-racing moguls like August Belmont Jr. who wanted blacks out of the jockey business. They succeeded, but not before Winkfield won the Kentucky Derby, America's most storied race (though at the time not its richest one), in 1901 and 1902. (Black riders won twelve of the first twenty-two Derbies, which was first run in 1875.)

In 1903, Winkfield double-crossed one of his employers, John Madden, by refusing to ride a horse for him after contracting to do so. This, combined with the move to eliminate black jockeys as competitors for "white" jobs and a general decline in horse racing during the early years of the century, propelled Winkfield to move his tack to Russia, where he became a star riding horses for Armenian oilmen like General Michael Lazarev and Leon Mantachev. It was here that he earned the nickname Black Maestro for his incredible ability to win races, to have his horses sprint at just the right moment. Other American jockeys rode in Europe—the money was good, as were the horses—but Winkfield became the most successful black to do so.

Winkfield returned to the United States during World War II, chased by the Nazis out of France, where he had gone after the Red Russians chased him from Russia, in a trek in which he shepherded more than 250 thoroughbreds from Odessa to Warsaw, the stuff of movies and myth. In the States, he worked for a time as a jackhammer operator but finally wound up back in racing as a trainer. Winkfield died in France in 1974, at the age of ninety-one, having received some recognition in the early '60s, when Sports Illustrated ran a major story about him. Other magazines, like Ebony, published articles on him just after he died. In nearly every case, Winkfield seemed more a curiosity than a revelation.

Drape's book is a lively, well-researched narrative, filled with compelling descriptions of the world of horse racing in both America and Europe and of its denizens, from John Keene, who aided Winkfield and who was kicked out of Europe for apparently doping his horses, to "Father" Bill Daly, who beat his apprentice jockeys, whom his brother literally bought from their parents, whenever they lost. There were gamblers like John "Bet-a-Million" Gates and George "Pittsburgh Phil" Smith and colorful white jockeys like Winnie O'Connor. In Russia, there was the huge Moscow Hippodrome, with its marathon track, its multiethnic stables, where several languages swirled, and its aristocratic crowds, who sometimes hobnobbed with the jockeys in elegant hotels. In a word, Drape's account is Dickensian, richly so. It does not so much replace as complement an earlier biography of Winkfield, Ed Hotaling's 2005 Wink: The Incredible Life and Epic Journey of Jimmy Winkfield. Drape's book is more straightforward, but there is context in Hotaling's that is not in Drape's—his comparison of Winkfield and Jack Johnson; his inclusion of more detail about the Russian Revolution and about historical characters who had nothing directly to do with Winkfield.

My only hesitancy about Drape's book is its tendency to see earlier black history through the lens of the civil-rights movement, so that all that precedes it seems to adumbrate it. In this account, Winkfield becomes something like a civil-rights pioneer. Nothing makes this clearer than the book's opening, in which Winkfield and his daughter attend a dinner at a segregated Louisville hotel in 1961 and are almost denied entrance through the front door even though he is an invited guest. At another point, Drape suggests that the demands of Russian workers that resulted in the Bloody Sunday massacre in 1905 "resonated with a black man from the Bluegrass." The book is not footnoted, so one has no idea where Drape got this impression. But it feels a bit like the author is reading civil-rights consciousness back into his subject simply because his subject is black. Winkfield was, like many gifted athletes, a narrow man and a fairly self-centered one: He knew and cared about horses and very little else. Perhaps all of us who are interested in pre-civil-rights-movement black history would do well to learn it well and, more important, to accept it on its own terms. The history is heroic enough without having to be made thoroughly contemporary, too, as if the only true heroes in this world were our own or those who were like them.

Gerald Early is Merle King Professor of Modern Letters at Washington University in St. Louis.