John Tenbrook Sterling

Two Men Captured Fourteen in the Battle’s Fury

John Tenbrook Sterling was born in 1841 in Edgar County, Illinois. During the American Civil War, he entered the United States Army and served with Company D of the 11th Indiana Infantry. He was still a private when he performed the extraordinary act at Winchester, Virginia, that would earn him the Medal of Honor.

By 1864, the Shenandoah Valley had become one of the most strategically important battlegrounds of the war. Confederate forces under Lieutenant General Jubal Early continued operating through the valley, threatening Union positions and forcing Washington to devote substantial forces to the region. Major General Philip Sheridan was given command of the Union Army of the Shenandoah with orders to defeat Early and eliminate the valley’s military importance to the Confederacy.

The campaign brought Sterling and the 11th Indiana Infantry into the fighting around Winchester.

On September 19, 1864, Union and Confederate forces collided in the Third Battle of Winchester, also known as the Battle of Opequon. The engagement developed into one of the largest and most violent battles ever fought in the Shenandoah Valley.

The battlefield was chaotic. Infantry formations advanced and counterattacked while artillery fired across open ground and wooded areas. Units became separated, casualties mounted, and control of the field shifted as both sides committed additional troops.

Sterling was serving as a private in Company D when he entered some of the hardest fighting of the battle.

During the engagement, Sterling and one fellow Union soldier succeeded in capturing fourteen Confederate soldiers.

The achievement was remarkable because the two men were operating during the most intense portion of the battle. Rather than simply guarding prisoners already separated from their unit, Sterling and his companion actively secured the surrender of a group far larger than themselves.

His official Medal of Honor citation preserved the achievement in concise language: with one companion, he captured fourteen of the enemy during the severest part of the battle.

The citation does not embellish the circumstances, and no unsupported details are necessary. The numbers alone illustrate the extraordinary nature of what happened.

Two Union soldiers.

Fourteen enemy troops.

And a battlefield around them still consumed by intense combat.

Sterling’s action formed part of a broader Union victory at Winchester. Sheridan’s forces eventually drove Early’s army from the field, forcing the Confederates to retreat south through the Shenandoah Valley.

The victory had important consequences. It weakened Confederate control of the region and opened the way for additional Union victories at Fisher’s Hill and, later, Cedar Creek. The series of defeats severely reduced Confederate military power in the Shenandoah Valley.

Sterling continued serving after Winchester and eventually attained the rank of corporal, the highest verified rank of his military career.

Recognition for his actions came before the Civil War had even ended.

On April 4, 1865, John Tenbrook Sterling was awarded the Medal of Honor for his conduct at Winchester. Only five days later, General Robert E. Lee surrendered the Army of Northern Virginia at Appomattox Court House.

Sterling therefore received the nation’s highest military decoration while the war was still technically underway.

The Medal of Honor had been established during the Civil War and was still a relatively new decoration. Sterling joined the early generation of Army recipients whose actions helped define what the award represented.

His recognition was based on one specific battlefield achievement: capturing fourteen Confederate soldiers with the assistance of only one companion during extremely heavy fighting.

His broader wartime service is also represented by the Army Civil War Campaign Medal, created decades later to commemorate qualifying service in the United States Army and volunteer forces during the conflict.

The two decorations represent different parts of Sterling’s military record. The Medal of Honor commemorates his individual courage at Winchester, while the campaign medal represents his wider service during the Civil War.

Sterling survived the conflict and lived for more than half a century after the guns fell silent.

During his lifetime, the Shenandoah Valley battlefields where he had fought became part of the national memory of the Civil War. Veterans gathered at reunions, wartime histories were published, and the Medal of Honor developed into the United States’ most prestigious decoration for military valor.

The young private who had fought at Winchester lived long enough to see those events become history.

John Tenbrook Sterling died on February 2, 1920, in Terre Haute, Indiana. He was buried at Bethesda Cemetery in West Terre Haute.

His legacy rests on a remarkable moment during one of the Civil War’s fiercest valley battles.

The fighting around Winchester was severe.

The battlefield was confused.

Enemy troops surrounded the advancing armies.

Yet Sterling and one fellow soldier managed to capture fourteen Confederate soldiers in the middle of that struggle.

For that extraordinary action on September 19, 1864, John Tenbrook Sterling received the Medal of Honor and secured his place among the decorated soldiers of the American Civil War.