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In 1890, much of Detroit's street railway system used outmoded technology, had severe labor and public relations problems, and faced uncertainty over the remaining length of the 30-year franchise granted by the city in 1863, but extended in 1879, perhaps illegally. An apparent solution came in 1891, when William W. Cook-later to earn a fortune that he would give to the University of Michigan Law School-and other "Eastern capitalists" purchased Detroit's street rail system. They were unable to solve the existing problems, and the new outside ownership itself added difficulties. Cook's group sold out in 1894, and over the next seven years street car lines consolidated, ultimately as the Detroit United Railway in 1901. The "war" between the city and the company continued until 1922 when the city finally bought the company. This made Detroit the first U.S. city to own its transit system, the Department of Street Railways, or D.S.R. Examining Cook's role provides information about his investments, his business relations, and his continuing connection to Michigan after he moved to New York City in 1882 from his Hillsdale home. The story also provides insight into the longstanding difficulties of providing effective transportation in southeast Michigan.