“ ‘Mr. Sherman (would to Heaven he were well at New Haven,) is against our sending our carriages over the ferry this evening, because it is Sunday; so we shall have a scorching sun to drive forty miles in, to-morrow. I wish I could send you his picture, and make it speak, and in the background paint the observations made on him here. But enough of this at present. I will have him drawn in Philadelphia, if it can be done at any reasonable rate.’[22]
“To judge these criticisms fairly we must remember that Deane was a man of fashion and of the world, while Sherman was neither. A plain country lad, a hardworking journeyman at his trade, a busy surveyor, a sagacious selectman, a shrewd store-keeper, a hard-headed lawyer, an industrious judge, he had qualities not of a kind that shine in polite society, but of a kind nevertheless that count in life, in every position which a man may be called to fill. He would have made a better figure with better manners. But a rusticity that would have ruined the advance of most men was everywhere tolerated in Sherman, because there was felt everywhere an admiration for his mind and heart,—his solid sense, wise forecast, and practical wisdom.
“While living in this town, Sherman was asked one day by a neighbor, the next time he went to the county seat, to retain counsel for him to bring a petition to court in a matter connected with the settlement of an estate. He noted down the facts which he thought it would be necessary to state in the papers prepared for such a proceeding, and the lawyer whom he consulted was so much impressed with the clearness and precision of the memorandum that he strongly advised him to adopt the legal profession.
“There were then no American, and, indeed, no English law schools. An education for the bar was commonly gained by studying the works of some of the English judges of former generations, under the advice of a local practitioner, but with little other assistance from him. The system of justice administered in Connecticut was rough and unhewn, and not a few of the judges of the highest courts had never followed the profession of the law.
“Sherman began to read law, in consequence of the incident to which I have alluded, when he was about thirty years of age, and was admitted to the bar in Litchfield County in 1754. There were then few lawyers in the colony who gained the whole of their livelihood from their profession. Many were also farmers. Sherman retained his interest in the New Milford store.
“Meanwhile he had been sent to the General Assembly, and made first a justice of the peace, and then a side judge of the County Court.
“The record of one of the early justice suits tried before him well illustrates the difference in political ideas between those times and ours. It shows the conviction and fine of one of his fellow-townsmen for a violation of the Colony statute in not attending public worship in any congregation allowed by law on January 29, 1758, nor on any Sunday in the month next preceding.
“ ‘Squire’ Sherman, as he was now called, brought to his new profession the strong common sense and good business judgment which had served to advance him in his previous employments, and which, if added to sound learning, will always assure success at the bar.
“The late President Porter, who, in early life, was settled as a minister at New Milford, once told me of a story which he heard here of some wise words uttered by Sherman at this period in his history. ‘Squire Sherman,’ said one of his neighbors to him, one day, ‘tell me, are most controversies that come before Judges in lawsuits decided justly or unjustly?’ ‘Sir,’ was the reply, ‘it’s not the point whether they are decided justly or unjustly: they are decided, and made an end of.’ And in truth it is perhaps the best office of courts of justice that, however often they may err in their processes, they certainly bring every human controversy that is within their reach to a final stop. The conclusion may be right or wrong; but a conclusion it is.
“Sherman was a deacon of the New Milford Church, the clerk and treasurer of the society, and one of the school committee. At the age of forty, he removed to New Haven, and connected himself with the White Haven Church, one of the two original bodies out of which grew the United Society and the United Church. Here again the records show his faithful work on committees and as collector of the rates imposed by the society.