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In 1890, St. Louis was the fourth-largest city in the country, with a population approaching five hundred thousand, and had begun the quintessential American form of urban growth—upward, via steel-framed, multistory buildings. Its industrial and commercial bustle, its surprisingly white crowds in which not even one person in ten was black, and its air filled with snatches of spoken German, Czech, and Italian must have appealed to Frederick. After spending just a few months there he headed even farther north to a city that epitomized the young, powerful, polyglot, brash United States.

By 1890, Chicago had captured the world’s imagination as the embodiment of the “American miracle.” In just two generations, a frontier settlement established in 1833 had grown into the second-largest city in the country, with a population of 1.1 million; it was overshadowed only by New York’s 1.5 million, and was the fifth-largest city in the world. Rather than being stunted by a devastating fire in 1871, Chicago’s growth accelerated in the last decades of the nineteenth century as the city rebuilt itself into a modern metropolis and became a center of industry, commerce, and transportation. Chicago, with the world’s first skyscrapers, became an icon not only of American technological prowess and economic might, but of modern industrialized civilization in general.

Emigrants from the Old World eager to reinvent themselves flooded into Chicago. They included Germans, Irish, Scandinavians, Poles, Lithuanians, Czechs, Italians, and Jews from several Eastern European countries. In 1890, an astounding 78 percent of the population had been born abroad or had foreign parents. An observer remarked that there were regions in the city where you could pass an entire day without hearing a word of English. It is bitterly ironic that American blacks, who were still concentrated largely in the South and who lived under conditions that were no better, and often worse, than those suffered by landless peasants in Ireland or impoverished laborers in Germany, did not have the same opportunities for change that many white foreigners were given. In fact, there were very few blacks in Chicago at this time; of the total population, they made up only 1.3 percent—about 15,000 people—with men somewhat outnumbering women. Even if many of the foreign emigrants in Chicago barely scraped out a livelihood and lived in filthy slums, they were at least given a chance to come to a place where they might be able to improve their lot. By contrast, Frederick’s arrival was part of a feeble trickle of native-born southern blacks who had started coming to Chicago in the years after the Civil War. The “Great Migration,” when hundreds of thousands would start streaming north in search of economic opportunity and to escape the intolerable conditions at home, would not occur until decades later, during and after World War I.

At first, Frederick got a job similar to the one he had in Memphis—except that this time he worked as a “boy” for a flower and fruit seller rather than for a butcher. Michael F. Gallagher was the owner of what was probably the most successful floral business in Chicago during the late 1880s and early 1890s, with a main store in the fashionable city center. On the eve of the Columbian Exposition of 1893, Gallagher opened a second store in an even more visible location on the city’s main lakefront thoroughfare and announced his newly achieved prominence by advertising his business as “Florists to the World’s Fair.”

Everything about Frederick’s first job in Chicago prefigures his future life and career. By working for Gallagher, he had entered what can be called an elegant service industry, one that existed for the benefit of people with money and social standing. No matter how lowly or demanding Frederick’s own labors might have been, he was nevertheless involved in providing adornments to those who could afford to pay for such luxuries. The kinds of customers he most likely saw and interacted with at Gallagher’s would also have presented him with models of gentility, and forms of posturing, that he would need to learn to understand and to satisfy.

Although Frederick had moved five hundred miles north of Memphis and a world away from the South, at the end of the nineteenth century blacks in Chicago were still hardly free to do or to become anything they wanted. After working for Gallagher for “8 or 9 months,” as he recalled, Frederick launched into a profession that would be his mainstay for the next twenty years as well as his springboard to wealth: he became a waiter. By setting out on this career path, Frederick also assumed one of the few roles that was available to him because of the racist labor patterns in the city.

One-third of the entire black population were employed in domestic and personal service, a category that included workers in Chicago’s myriad restaurants and hotels, in private homes, and on trains as Pullman porters. When Frederick entered the profession around 1892 there were some 1,500 black men working as waiters everywhere in the city, from chains of inexpensive restaurants to elegant hotels.

Especially in the upscale dining rooms, the black waiter’s job in those days was complex, demanding, and competitive—more so than is usual today, and differently. By reacting immediately and cheerfully to the client’s wishes—and all the clients in the expensive restaurants were white—the black waiter could be seen as simulating the enforced obsequiousness and racial subordination that had been, and still was, the norm for all blacks in the South. Even if the diner was a lifelong northerner for whom slavery had been an abomination, he would still be likely to enjoy the sense of privilege and worth that an exaggeratedly deferential black waiter would confer on him for the duration of the meal. An efficient waiter who strived to be likable also got bigger tips.

However, black waiters in Gilded Age America were not just gifted or cynical actors. They also took pride in their profession, which required tact, charm, dignified deportment, and mental and physical agility. Waiters who served the financial and political elite in the grand hotels and restaurants of the nation’s second-largest city acquired an enhanced sense of personal worth as well as a heightened social status in their own communities.

If the first job one has in a given profession acts as a tuning fork for the career that follows, Frederick started at a pitch of the highest quality. The Auditorium Hotel, where he began as a waiter, was the most important new building in Chicago and had one of its most elegant and modern dining rooms. Built between 1887 and 1889 on what is now South Michigan Avenue, it was hailed at the time of its completion as the “chief architectural spectacle of Chicago,” a symbol of the city’s civic progress, and even hyperbolically as the “eighth wonder of the world.” Frederick had found his niche in urban life: after the Auditorium Hotel he spent the next “one and a half years as waiter” in other restaurants in the city.

Frederick left Chicago around the summer of 1893, a momentous period in the city’s history. The World’s Columbian Exposition opened on May 1; on May 9, a banking crisis began, which led to a national economic depression that became known as the Panic of 1893. When the economy collapsed, thousands of workers, including those who had been attracted to the city during the boom period of the world’s fair, were left without jobs or prospects of any kind.

Frederick decided that he could do better by heading to New York City. From all accounts, the situation was not as bad there as in Chicago. New York also had more of everything that had originally made Chicago attractive—more people, bustle, excitement, power, towering buildings, and hotels and restaurants where one could find work. New York was the only city in the United States that ambitious Chicagoans envied. And the only siren call that ambitious New Yorkers heard came from the great cities of Europe.