At Rogers, Bowen & Rogers, Grover Cleveland began the study of law and soon showed that he was a youth of intelligence and character. At 19 years old he was earning $4.00 per week salary, a sum that he was able to maintain himself and even assist his mother. He was admitted to the bar in 1859, but remained four more years with the firm, thus securing eight years of legal training. After being admitted to the bar, he began as chief clerk with the firm at a modest salary of $600.00 per year and his salary increased year by year until the latter part of 1862 when at age 25 it had reached $1000.00 He was just beginning to earn something by which he could assist his mother and sisters even more when the war came on. It was a question in the family whether he should enter the army or not; but at a kind of family council it was decided that his two brothers, one a little older and one a little younger than Grover, should go to the army, and that he should remain in the practice of the law and assist his family.

As a young lawyer he became so favorably known that in the year 1863 he was appointed assistant district attorney for the county of Erie at an annual salary of $600.00. Even though he was taking a pay cut, he felt that this position would give him a quick and effective way of achieving an independent place in his profession.

During his term as assistant district attorney he was drafted into the union army. Two of his brothers were already in the army and since his family was dependent on his earnings, it was decided that he would obtain a substitute to take his place in the army, which was a common occurence in such family situations. His superior , the district attorney also didn't want to part with his services, so he lent Grover the money to obtain a substitute.

This position he filled in a manner so competent that in 1865 he received the nomination of the Democratic party for the position of district attorney for his county, but was defeated by the Republican candidate, close friend and roommate, Mr. Lyman K. Bass. One night when Cleveland had returned home he was greeted by his roommate, Mr. Bass, who said: "Well Cleve, I have been offered the nomination for District Attorney against you." Grover's reply was: "Well, why don't you take it?" Mr. Bass did and was elected by a narrow majority.

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