Young Winston attended West Point from August 1859 until resigning at the end of 1860. Governor A. B. Moore appointed him a 2nd Lieutenant in the Army of Alabama, but the Confederate government at that time did not accept troops enrolled for a term longer than twelve months. During the summer he raised a company for twelve months service, but at that time (August 1861) the War Department wasn't accepting twelve month companies from Alabama. Winston couldn't pursuade his men to change their enlistment to a longer term, so they disbanded, leaving him without a command or a commission.

Winston then went to Hunstville to drill volunteers at Camp Bradford. On Nov. 5, 1861, he was issued a commission as Cadet which Winston accepted at his father's home at Valley Head AL, Dec. 2, 1861. On Dec. 18, 1861, he received an assignment from the War Department, reporting from Green Pond SC on Feb. 28, 1862. Winston died of measles at Chapman's Fort SC, Apr. 11, 1862. Effects claimed by his father included a sword and belt.

William O. Winston, Jr. died in Confederate service without ever being assigned to a specific command. In terms of raising troops for Confederate service, he also found himself at the wrong place at the wrong time. It was not as easy as it seems to us today.

Winston Plantation Home near Mentone AL is a bed and breakfast inn which I highly recommend.
http://www.mentonealabama.org/Strayhorn/StrayhornCivilWar.htm