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After becoming a lawyer, Cleveland worked for the Rogers firm for three years, leaving in 1862 to start his own practice.
In January 1863, he was appointed assistant district attorney of Erie County.
With the American Civil War raging, Congress passed the Conscription Act of 1863, requiring able-bodied men to serve in the army if called upon, or else to hire a substitute.
Cleveland chose the latter course, paying George Benninsky, a thirty-two year-old Polish immigrant, $ 150 to serve in his place.
As a lawyer, Cleveland became known for his single-minded concentration and dedication to hard work.
In 1866, he defended some participants in the Fenian raid of that year, doing so successfully and free of charge.
In 1868, Cleveland attracted some attention within his profession for his successful defense of a libel suit against the editor of the Commercial Advertiser, a Buffalo newspaper.
During this time, Cleveland lived simply in a boarding house ; although his income grew sufficient to support a more lavish lifestyle, Cleveland continued to support his mother and younger sisters.
While his personal quarters were austere, Cleveland did enjoy an active social life and enjoyed " the easy-going sociability of hotel-lobbies and saloons.

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