As bearing upon his political career, it may be narrated, that in the Fall of 1839, he was elected prosecuting attorney of the county, at which time the Whig party was largely in the ascendancy, commanding from 1,500 to 2,000 majority, though he was a Democrat and nominated by the Democrats for the office. Two years later, at the expiration of his term, he was strongly solicited by both parties to take the office another term, but declined in consequence of the inadequacy of the salary. An incident occurred during his term as prosecuting attorney which had a marked effect upon the politics of Cleveland and its vicinity. Up to 1841, slave-owners were in the habit of sending their agents to Cleveland and causing their runaway slaves to be arrested and taken before a magistrate, when a warrant would be obtained to return the slave, and he would be carried back into slavery. All this was done openly and publicly, creating little or no excitement, and Mr. Bolton, in the practice of his profession, was more frequently employed for this purpose than any other attorney in the city. In the Spring of 1841, three negroes, who were claimed as slaves, had run away from New Orleans and were in Buffalo. The agent of their master applied to a law firm in Cleveland for assistance. At that time, slaves arrested in Buffalo were in the habit of claiming a trial by jury, which was granted. To avoid a jury, with its sympathies, it was thought advisable to get the negroes into Ohio, and, accordingly, one of the attorneys, the agent and a negro of Cleveland, repaired to Buffalo. On their return the three negroes came with them, and it was said they had been kidnapped. On their arrival at Cleveland, the negroes were arrested under the law of Congress as fugitives from service, and lodged in the county jail. This information coming to the ears of the few Abolitionists then in the city, among others the late Hon. Edward Wade and Hon. John A. Foot, lawyers at the time in full practice, they applied to the jailor for admission to consult with the negroes. But public opinion was so strongly prejudiced against the Abolitionists that neither the jailor nor the sheriff would permit any of them to communicate with the prisoners. Accidentally, a colored man inquired of Mr. Bolton if he would take up their defence. He readily assented, and being prosecuting attorney of the county, and it being well understood that he was not an Abolitionist, the doors of the jail were readily opened to him, and he immediately made preparations for a vigorous defence of the prisoners. A writ of _habeas corpus_ was immediately applied for to Judge Barber, one of the associate judges at the time; the negroes were brought before him, and their case continued for ninety days, to prepare for a defence.