Samuel Phipps, the son, was graduated at Harvard College in the class of 1671, the last class under President Chauncy, and the only one in twenty consecutive years to consist of more than ten members. The illustrious member of the class was Samuel Sewall, the judge, who was on the bench at the witchcraft trials, whose diary, long since in print, is of immeasurable value, historically. Proceeding to the degree of Master of Arts, Samuel Phipps assumed the mastership of the grammar school in Charlestown, and taught it ten years. At one time he had fifty-three scholars. At the close of his school he was elected a constable at the town meeting, which he refused. The town insisted. Phipps appealed to the governor, claiming that, as Master of Arts and a grammar school master, ‘it was unreasonable and not customary to choose persons so qualified and improved.’ The government excused him, but the town still resolved not to comply with the order. Notwithstanding this breeze, Phipps served against his will, and, in the succeeding year, was town treasurer, and afterward town clerk, selectman many years, and again constable. In 1689, Samuel Phipps was elected county clerk, and served to 1723, and register of probate, 1692 to 1702, and register of deeds, 1693 to 1721. He represented Charlestown in the general court of 1692, the first under the new charter of William and Mary, which erected the colony into a province, with a royal governor. Ten other years Phipps served as representative. In 1704, he was a captain of the foot company at Charlestown.
Captain Phipps was three times married. First, in 1676, to Mary Phillips, a daughter of Henry and Mary (Dwight) Phillips,