William Shy enlisted in the 20th Tennessee Infantry Regiment as a private in 1861, rising through the ranks and taking part in many notable battles through the years that followed. The 20th Tennessee, part of the Army of Tennessee, was under the command of Gen. John Bell Hood in the latter years of the war. In 1864, Hood and the Army of Tennessee embarked on the mission to regain control of Middle Tennessee, and the series of battles relating to this goal became known as Hood’s Tennessee Campaign. The Army of Tennessee had fought its way to Nashville by December 1864, and the campaign’s success or failure relied upon Gen. Hood’s ability to maintain control of hills south of the city of Nashville. The Army of Tennessee, battered and broken at the Battle of Franklin just weeks before, stretched itself thin between Compton’s and Peach Orchard Hills. The Confederates managed to hold Compton’s Hill on December 15, 1864, the first day of fighting in the Battle of Nashville. By the second day, Compton’s Hill was surrounded on three sides by attacking Federal troops. Shy, then commander of the 20th Tennessee Infantry Regiment, refused to surrender, maintaining control of Compton’s Hill through the rain and barrage of Federal bullets until the Federal attack intensified. After a few minutes of intense fighting, the Federals overwhelmed Shy’s force. Only 65 men escaped, and Shy himself had fallen, at age 26, from a close-range shot to the head. With the fall of the Shy’s position, the Army of Tennessee was completely routed from the field on the evening of December 16, beginning a 250 mile long retreat to Tupelo, MS. The disastrous Tennessee campaign would ultimately cost Gen. Hood his command; he was replaced in January 1865. In honor of Shy’s courage and heroics on Compton’s Hill, the hill was renamed Shy’s Hill.
- Refused to surrender Compton's Hill in the face of intense fire during Battle of Nashville
- Died in battle, and the position fell to Federals
- Hill was renamed Shy's Hill in his honor