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Upon returning to the United States, McDonald had to establish himself in business first. He settled in Chicago in the 1870s, becoming a successful stockbroker amid the city’s-era gilded boom. By 1900, his financial acumen earned him a move to New York, where he joined the brokerage firm of C.D. Barney—precursor to today’s Morgan Stanley. This growth enabled him to amass substantial wealth, which he later invested in his passions.