First Lieutenant and Adjutant 14th Mass. Vols. (Infantry), July 15, 1861; discharged, on resignation, January 24, 1862; lost at sea, February, 1862, on a voyage to Cuba, undertaken on account of a fatal disease of the lungs contracted in the service.
At the Freshman examination of Harvard University, in 1837, I will remember to have observed, among my future classmates, a tall, erect young man, of demure aspect and rather sedate motions, with blue eyes and closely curling fair hair, who was pointed out by some one as Charles Simmons, with the prediction that he would be our first scholar. He came with an intellectual prestige, based less upon his own abilities than upon those of his two elder brothers, both of whom had been accounted remarkable for gifts and culture. Such a reputation is often rather discouraging to a younger brother, if it demands from him a career in any degree alien to his temperament. Perhaps it was so with Simmons. He certainly seemed rather to shrink from the path of college ambition than to pursue it; and his academical career, though respectable, was never brilliant. He was the youngest son of William and Lucia (Hammatt) Simmons, and was born January 27, 1821. His mother was a native of Plymouth, Massachusetts; his father was also born in Plymouth County, and was for many years one of the Justices of the Police Court in Boston. Charles was fitted for college partly at the Boston Latin School, and partly by his brother, Rev. George Frederick Simmons. In college I had never much personal acquaintance with him, but vividly remember the implied contrast of his grave manners and fastidious air with the witty sayings and mirthful feats attributed to him by his few intimates. This partial antagonism had indeed a peculiar zest for the whole class, when exhibited in his public declamations, which were rather  noted among us; since he usually selected some serio-comic passage, which was recited with the gravest face and the most irresistible humor. He was shy, sensitive, proud, and reticent. But he was exceedingly faithful to his friends and to his avowed principles, manifesting in this way a sort of chivalrous spirit, which indeed brought upon him his only serious college censure. In some undergraduate disaffection, in our Senior year, he stepped forward to take a conspicuous position, from which the other leaders shrank, and he was deprived of his degree in consequence. It was bestowed upon him fourteen years after, on the earnest petition of his classmates. He afterwards studied law with David A. Simmons, Esq., a relative, and was admitted to the Suffolk bar. For the rest of his life he had an office in Boston, with a moderate chamber practice. But apparently the same qualities which had impaired his collegiate success followed him into professional life also. Over-sensitiveness, ill health, and perhaps some want of resolute purpose, always kept him back, while other men more fortunately constituted won an easy success. He remained unmarried, and rather shunned general society as well as public affairs. Yet he had excellent judgment in practical matters, and held decided views on the questions of the day; having become, for instance, strongly anti-slavery in his convictions. But he seemed by temperament a scholar and a critic rather than a man of affairs. He was especially a student of the natural sciences; had much knowledge of music, and a rare taste in all matters of art. His love of nature grew with his years; and his chief pleasures, beyond books and music, were found in country life, among ‘God's fresh creations,’ as he himself said. Never demonstrative in manner, he became less so as he grew older, and to strangers seemed cold and uninterested. He was reserved even with his intimates; and it was, as I am assured, a matter of surprise to his nearest friends when they heard of his enlistment, through his own letters from Fort Warren. The attack on our troops in Baltimore had, indeed, seemed  to excite him very much. He had described hearing the departure of the regiments from Boston, in the middle of the night, two days after; was very much impressed by it, and he said then that, if he had not from boyhood ‘despised soldiering,’—and so did not know the use of a gun,— he should have gone off with some of the three-months men. So he joined two different classes in Boston, for the purpose of drilling, and said that when he knew enough he should go. But he went at last very suddenly, in July, without having time to arrange his business affairs; for Colonel William B. Greene, who had been his friend for several years, came home from Paris to take part in the war, and, finding this recruit ready, made him his Adjutant at once in the Fourteenth Massachusetts. His letters describe his interview with Colonel Greene, and his enlistment.
In the same letter he thus speaks of the soldiers:--
“Our regiment,” the Fourteenth Massachusetts, or “Essex,” has as good material as ever marched out of the old Commonwealth. All from Essex County. Stalwart, sober men, all of them. Whether we succeed in drilling them to form squares, direct and oblique, or not, during the short ten days we have left, I will warrant every company of them to make face against cavalry, even in line, before turning their backs and taking to the woods. If they allow themselves to be “cut up,” without killing man for man, call me no prophet.The change in his mode of life seemed to transform his whole nature. This shy, contemplative, lonely, middle-aged  man, for whose fastidious nature the daily intercourse of Court Street had been far too rough and harassing, entered with a sort of enthusiastic delight upon the duties of a regimental adjutant,—perhaps the most wearing and vexatious functions which the army has to offer, and such as seem to demand all the energy of youth and all the equanimity of health. His first letters from camp were very ardent. The details of camp life, the noise and routine of military affairs, which before had appeared either absurd or tedious, now excited and interested him very much. The desire, as he expressed it, ‘to strike a blow for the old flag we were all born under,’ seemed to make him forget all annoyances; and he worked there, and through his whole military life, as he perhaps had never worked before. And though it ended in disappointment, both for the regiment and for himself, yet his duty was done with his accustomed thoroughness, as his letters show.
 The regiment had very hard service at first, and then was converted into heavy artillery, and kept at Fort Albany, with always a hope of being ordered into active service. The climate was formidable, in respect to fever and ague, and at one time they had a hundred and twenty men on the sick-list from this one cause. Simmons was also ill for a time with this disease, early in September, and perhaps never fully recovered from its effects. The change of armament and service necessarily threw very hard work upon the Adjutant, because of the great amount of writing required; and then, before having any opportunity to take part in active service, he was taken ill again, and felt that he could never do anything more. It was a bitter disappointment. Apparently he had never dreaded the thought of death,—certainly not of being killed in battle, —but to be a permanent invalid was an appalling prospect. After his return he said, indeed, that, had his position been one where an invalid could have been of any service, he would gladly have remained and have died in his place. After a severe exposure, one October night, he was attacked with violent congestion of the lungs, followed by bleeding; but he tried for some time to convince himself that he was gaining, and would not apply for leave of absence, being at last decisively ordered away by the surgeons. The following letters tell the story:—
He obtained leave for sixty days absence at first; and after a short journey to one or two places, he decided to accept the invitation of a classmate and friend, and visit him in Minnesota. For a little while he seemed better, but it did not last long, as these letters show:—
He at last offered his resignation, which was accepted, to date from January 24, 1862. It was the heaviest disappointment he had ever met, and at first it seemed more than he could bear with equanimity; but when it became certain that he was fatally diseased, he grew more cheerful and more like himself, as if feeling that it would have been useless for him to remain in the service. He never had seemed more thoughtful for others, more patient himself, than during these last days. He finally sailed, on February 25th, for St. Jago de Cuba. All who saw him felt that they were never to see him again, although they anticipated no such sudden calamity as that which occurred. The vessel sailed with a fine breeze, but was never heard of again. The next day there were very high winds, and it was supposed that she had been struck by some gale, and had sunk at once, for no trace of her was ever found. A vessel which sailed a few days later was nearly wrecked near the Gulf Stream, and it was thought that this disaster might have proceeded from one end of the gale which had sunk the other vessel. It is the impression of some of his most intimate friends, that, if he could have chosen, he would not have regretted his sudden departure in such a way; for he could feel that he was dying with the well and strong, and not in his character of invalid, which, as he himself said, he ‘particularly detested.’  For the last month that he had remained in Massachusetts, while growing weaker all the time, he had retained all his interest in his regiment. He expressed peculiar pleasure in recalling his intercourse with the men; saying that he felt sure he had been useful to many of them, and that only the pleasantest relation had existed between them and him. Great as was his disappointment, he certainly never regretted his participation in the war. He said once that it was a great satisfaction to him to think that if he had stayed at home he should have been better off in money affairs, for his business had increased since he went; so that it was proved to himself that he went from patriotic motives. He also liked the thought that, had he stayed at home, he probably would not have been thus mortally diseased; for his lungs had been pronounced perfectly sound by the physicians of a Life Insurance Company before he entered the service. He could feel that it was a vigorous life and a prosperous fortune of which he had made the sacrifice. There was something noble, not selfish, in the feeling that led him thus to dwell, in what he knew to be the closing period of his life, on the offering thus given to his country,— to rejoice that he had been permitted to give it, and that he had possessed so much to give.