Charles White Whittlesey, a 37-year-old attorney and decorated World War I hero, vanished on November 26, 1921, after boarding the SS Toloa in New York for a voyage to Havana, Cuba. That evening, Whittlesey dined with the ship's captain and was reportedly in good spirits. He was last seen leaving the smoking room at approximately 11:15 p.m., stating he was going to bed. He was never seen again and was reported missing the following morning at 8:00 a.m.
Prior to his departure, Whittlesey had settled his affairs. He drafted a will leaving his property to his mother, paid a month's rent in advance for his home, and prepared nine letters to friends and family. These letters, along with a note for the captain detailing the disposal of his luggage, were discovered in his cabin. The contents of the letters, which were not written on the ship's stationery, have never been made public by the recipients. It is believed Whittlesey took his own life by jumping overboard, though no one witnessed the act and his body was never recovered.
Born in Florence, Wisconsin, Whittlesey later moved to Massachusetts and graduated from Williams College and Harvard Law School. He established a law practice in New York City but enlisted in the Army a month after the United States entered World War I in 1917. During the Meuse-Argonne offensive, he commanded the "Lost Battalion," a group of several hundred American soldiers surrounded by German forces. For his valor in holding his position despite being cut off for five days, he was awarded the Congressional Medal of Honor.
After the war, Whittlesey returned to his law practice and was frequently invited to speak about his wartime experiences. In November 1921, he served as a pallbearer at the burial of the Unknown Soldier at Arlington National Cemetery. Just days later, he booked his passage on the SS Toloa. Due to the circumstances and the passage of time, his disappearance is no longer under investigation.Last Seen: Nov 26, 1921
