His proposed destination was Cleveland, Ohio; his cherished ambition the study and practice of the law. He was accompanied on his journey by a young friend of kindred aspirations. Arriving at Buffalo he called on an uncle, Mr. Lewis F. Allen, who had a fine stock farm, just out of the city, and who finally induced him to remain there, promising to secure him admission to a law office in Buffalo. He remained with his uncle for a time, assisting him in the preparation of the manuscript of the “American Herd Book,” a work upon which he was then engaged; but in the course of a few months (in August, 1855) he secured admission as a student in one of the best known law offices of the city—that of Rogers, Bowen, & Rogers. Blessed with good health and industrious habits, with an earnest determination to succeed, he entered upon the work before him. For a time he boarded at his uncle’s house, taking the long walk to and from the office at morning and night; but after a few months he was enabled to be of such assistance in the office in clerical and other work, that, from the modest compensation allowed, he secured lodgings in the city and provided for all his humble wants.
After four years of unremitting study and toil, he was admitted to the Erie county bar, having laid the foundation for future professional success in a thorough mastery of legal principles and all the details of practice, and in those well-established habits of thought and application by which his subsequent life has been so fully characterized. He had gained, also, the confidence and esteem of his preceptors and employers, and after his admission continued with them as confidential clerk in charge of the office business, receiving a salary which enabled him, then, to contribute materially to the assistance of his mother in providing for the wants of the family and maintaining the comforts of the humble home in Holland Patent, toward which his fondest thoughts have turned in all the years of his busy life, and where such periods of recreation as he has felt warranted in indulging have mainly been spent.
In 1863 Mr. Cleveland received an appointment as assistant district attorney for Erie county, a strong testimonial to the legal abilities of so youthful a practitioner, considering the array of professional talent in the county and the responsibilities of the position. The war was then in progress; two brothers, one the next older, and the other younger than himself, had enlisted in the Union army; and when, a few months after his appointment, as he had fairly familiarized himself with the details of important cases intrusted to his care, he was himself drafted, he pursued the only practicable course, and provided a substitute for the service. In the fall of 1865, while yet serving as deputy, he was unanimously selected by the Democratic Nominating Convention as candidate for district attorney. The county was strongly Republican, but young Cleveland received a support beyond his party strength and was beaten, by a few hundred majority only, by the Republican nominee, Lyman K. Bass, then and since his warm personal friend.