Early Life
Stilwell was born on March 19, 1883, in Palatka, Florida of patrician Yankee stock. His parents were Doctor Benjamin Stilwell and Mary A. Peene. Stilwell was an eighth generation descendant of an English colonist who arrived in America in 1638, whose descendants remained in New York up through the birth of Stilwell's father. Named for a family friend, as well as the doctor who delivered him, Joseph Stilwell, known as Warren by his family, grew up in New York, under a strict regimen from his father that included an emphasis on religion. Stilwell later admitted to his daughter that he picked up criminal instincts due to,"...being forced to go to Church and Sunday School, and seeing how little real good religion does anybody, I advise passing them all up and using common sense instead."
Stilwell's rebellious attitude led him to a record of unruly behavior once he reached a post-graduate level at Yonkers High School. Prior to this last year, Stilwell had performed meticulously in his classes, and had participated actively in football (as quarterback) and track. Under the discretion of his father, Stilwell was placed into a post-graduate course following graduation, and immediately formed a group of friends whose activities ranged from card playing to stealing the desserts from the senior dance in 1900. This last event, in which an administrator was punched, led to the expulsions and suspensions for Stilwell's friends. Stilwell, meanwhile, having already graduated, was once again by his father's guidance sent to attend the United States Military Academy at West Point, rather than to proceed to Yale University as originally planned.
Despite missing the deadline to apply for Congressional appointment to the military academy, Stilwell gained entry through the use of family connections who knew President William McKinley. In his first year, Stilwell underwent hazing as a plebe that he referred to as "hell." While at West Point, Stilwell showed an aptitude for languages, such as French, in which he ranked first in his class during his second year. In the field of sports, Stilwell is credited with introducing basketball to the Academy, and participating in cross-country running (as Captain), as well as playing on the varsity football team. At West Point he had two demerits for laughing during drill. Ultimately, Stilwell graduated from the academy, class of 1904, ranked 32nd in a class of 124 cadets. His son, Brigadier General Joseph, Jr., {West Point 1933} served in World War II, Korean War, and Vietnam.
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