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Chester A. Arthur II, the son of Ellen Lewis Herndon and President Chester Alan Arthur, was born on July 25, 1864 in New York City. He was the couple's second child. Their first child, a son named William Lewis Herndon Arthur, was born in December 1860, and died in July 1863 from a swelling of the brain. As one would expect, Nell Arthur grieved the loss of her first child. Her husband wrote, "Nell is broken hearted. I fear for her health." Because of the tragic loss of their first child, they pampered their second son. Author Sandra Quinn wrote that the younger Chester Arthur "led a life that closely resembled that of European royalty." He was dressed in fine clothes, and he learned to sail and ride. His parents did not pressure him to perform well academically.
The Arthurs had a a third child, their daughter Ellen "Nell" Herndon Arthur, who was born in 1871. The family lived at 123 Lexington Avenue in New York. Ellen Arthur, the former southern belle from Virginia, held musical recitals, dinners and other parties at home and was a tremendous support for her husband's professional and political ambitions. Chester Arthur Sr. was a mover and shaker in the world of New York Republican politics.
His parents' marriage had its difficulties due to his father's frequent absences from the home while he was politicking. Ellen Arthur had difficulty accepting her husband's late hours and high living. She died in 1880 of pneumonia, before Arthur was selected to be James Garfield's running mate in the 1880 presidential election. Despite the difficulties in the marriage, Chester Alan Arthur Sr. took his wife's death very hard and it is said that it changed him. He became more attentive to his children at first, although he was criticized by some for showcasing them for political purposes. When Arthur became president, White House social affairs and administrative work began to edge out his family life and this put a strain on his relationship with his children.
Some have speculated that Chester Alan Arthur II may have developed a "live for the moment" attitude about life because of his mother's early death at the age of 42. When
President Arthur would "showcase his children" during White House parties, his daughter Ellen did not like the attention, but Chester Arthur II was more receptive, causing him to prefer a life of leisure over one of professional ambition. He gained the nickname "the Prince of Washington" for the way he used his status as the son of the President. He attended White House receptions and loved using the presidential yacht.
Chester Arthur II attended College of New Jersey (later named Princeton University) during his father's presidency. It is said that he would take the train his college to Washington, D.C., where he would "party into the wee hours of the morning". He learned to play the piano and also the banjo.
Chester Arthur II was at his father's side at the family's 123 Lexington Avenue house when President Chester A. Arthur died in 1886. Shortly before his father's death, at his father's request, he burned his father's official papers. They filled 3 garbage cans.
Arthur and his sister remained close until her death in 1915. He had once told a friend that he believed that when his sister Ellen married, he would lose all connections with any family. When Ellen became engaged, she told her brother that he was not losing her and that getting married wouldn't change their close relationship.
Arthur graduated from the College of New Jersey in 1885. He studied law at Columbia Law School, and planned to take over his father's law firm in New York City. Be he lacked his father's work ethic and he withdrew from law school before he completed his studies. In 1887, he sailed to Europe and stayed there for nearly 13 years. His was able to travel every major European city in luxury due to his inheritance from his father. He befriended Albert Edward, the Prince of Wales, who called Arthur "the perfect pattern of an Edwardian gentleman and of a Europeanized American." Contemporary accounts described Arthur as "tall, handsome and athletic." While in Europe it is said that he cultivated the company of "female admirers", good cuisine, and horses, particularly "driving horse-drawn carriages throughout the French countryside." By this time, he preferred to be called Alan. He lobbied to become Ambassador to the Netherlands in 1897, but was unsuccessful.
Chester Alan Arthur II married wealthy divorcée Myra Townsend Fithian Andrews on May 10, 1900 at the English American Episcopal Church and at a civil ceremony in Vevey, Switzerland. The couple returned to the United States later that year and bought a home in Colorado Springs, Colorado. They also kept a residence in Europe. The move to Colorado was made for health reasons. By this time, he was suffering from asthma and bronchitis. The couple's son, Chester Alan Arthur III, was born March 21, 1901. They also had a daughter, named Ellen for Arthur's mother and sister, but she died shortly after birth.
The couple lived on income from their mutual investments, which including Arthur's interest in the 250,000 acre cattle ranch, Trinchera Estate. In addition to raising cattle, his company mined gold, cut timber, and created a game park reserve for antelope, elk, and bison. Arthur's health improved in the Colorado climate. He became president of Cheyenne Mountain Country Club between 1905 and 1908. He also provided funding for facilities at the club. Polo became a favored sport as the result of top polo players to the area. As Vice President, Theodore Roosevelt came to Colorado Springs in 1901, he had dinner at the Arthur's home, Edgeplain, and attended a polo match during his visit.
Myra and Chester Arthur II divorced in 1927 due to his infidelity, drinking and partying. Myra learned that her husband has been having an affair in 1909. She decided to remain in the marriage for the sake of her son. The couple reconciled, but had a rocky marriage until they divorced. Arthur married Rowena Dashwood Graves in 1934. At the time she was 39 and he was 70 years of age.
Arthur died on July 18, 1937 in Colorado Springs. An obituary describe Arthur as an "internationally known sportsman, art connoisseur and son of the late President Chester Arthur." His wife Rowena died in 1969.
His son, Chester Alan Arthur III (known as Gavin) rejected the elegant lifestyle and pursued political and social issues instead. In 1930, he founded the magazine, Dune Forum, which promoted communication between the masses and intellectual elite. He was a member of the Utopian Society of America with John Updike, and in the 1950s he taught at San Quentin State Prison. By the late 1950s, he moved to San Francisco and was part of the Beat Movement. He was a friend of poet Alan Ginsberg. In 1966, he wrote The Circle of Sex, a book about gay, bisexual, and gender issues in astrology. At the end of his life, in 1972, he was a was an advocate for gay rights. He identified as bisexual. He had been married to three women. He was the last living descendant of President Chester Alan Arthur.