William Deering married Abby Reed Barbour in 1849. On July 31, 1852, their son Charles Deering was born in South Paris, Maine. Abby Reed Deering died two years later from common measles. In 1856, William Deering then married Clara Cummings Hamilton. Clara Hamilton gave birth to one more son and one daughter – James Deering and Abby Marion Deering. They were a very close family and shared business and well as social associations throughout their lives. Charles Deering, a Civil War child, was enthralled by stories of naval heroics. He entered the U. S. Naval Academy as a cadet midshipman when he was sixteen years old. He excelled at mathematics, geometry, calculus, marine surveying, astronomy, and navigation. In 1873, he graduated second in his class. Charles’ roommate and best friend, William Henry Schuetze, graduated in the top position. Soon after graduation, Charles served on the flagship of the European squadron, and later was assigned to duty in Asiatic waters. Charles met and married Ana Rogers Case, daughter of Rear Admiral Augustus Ludlow Case, U.S.N. In 1874 and 1875, he served aboard the U.S.S. Alaska, a 250-foot gunboat. He was promoted to Ensign in the summer of 1874. Ana gave birth to Charles’ first son, Charles Case Deering, and unfortunately in 1876, Ana passed away from an infection shortly after giving birth to their son. Charles continued his service. From 1877 to 1879, he was on duty aboard the U.S.S. Kearsage—at the time, a new Pennsylvania-built 200 foot iron gunboat—and the Alert. He received a promotion to Master (equivalent of Lieutenant—junior grade) late in 1878. He was assigned to duty in the Orient, and soon after he became acquainted with the ports and peoples of the Orient, Ex-President Grant made his famous trip around the world. Upon meeting Charles, General and Mrs. Grant were so much attracted to Charles’ courteous and affable manners and his tact in dealing with foreign officials that they asked that he serve as their personal escort. Mr. Deering spent a total of twelve years in the Navy, eight years of which were spent in France and Spain where he befriended many artists and collected much of his artwork and furnishings. He was a man of modest income when he first began to purchase a few pieces from individual artists he called friends. Swedish master artist Anders Zorn, American portraitist John Singer Sargent, and Spanish Modernista painter and poster maker Ramon Casas i Carbo were among his closest associates. On May 1, 1881, Charles Deering resigned from the Navy at his father’s urging to join the growing family business. Charles became the Secretary of Deering Harvester Company. He established his primary home at Evanston, on the shore of Lake Michigan. On January 2nd, 1883, Charles married Marion Denison Whipple, daughter of Major General William Denison Whipple. Charles and Marion had three children – Roger, born in 1884; Marion, born in 1886; and Barbara, born in 1888.