John Sullivan

He Spent Two Nights Behind Enemy Defenses

John Sullivan was born on March 17, 1840, in New York City. During the American Civil War, he entered the United States Navy and served as a Seaman aboard USS Monticello, a Union gunboat operating along the Confederate coastline.

By 1864, Wilmington, North Carolina, had become one of the Confederacy’s most important remaining ports. The entrance to the Cape Fear River was protected by formidable coastal defenses, and blockade runners continued using Wilmington to bring desperately needed supplies into the Confederacy. Understanding those defenses was therefore critically important to the Union Navy.

USS Monticello was among the vessels operating off the North Carolina coast as Union commanders gathered information about the approaches to Wilmington and prepared for future operations against its defensive system.

John Sullivan’s defining mission began on June 23, 1864.

He joined a reconnaissance party sent from Monticello to investigate the harbor and water defenses surrounding Wilmington.

The mission would continue for two days and two nights.

Unlike a conventional naval engagement fought from behind the guns of a warship, this operation required sailors to enter territory where Confederate forces could discover them at almost any moment. Their objective was intelligence—learning as much as possible about enemy communications, movements, and defenses without being captured or destroyed.

Sullivan and the men accompanying him pressed forward despite the constant danger.

During the reconnaissance, the party captured a Confederate mail carrier along with the mail he was carrying. The captured correspondence offered the possibility of valuable intelligence about Confederate positions, communications, and military activity.

The sailors also cut a telegraph wire.

During the Civil War, telegraph lines allowed commanders to transmit information far more rapidly than messengers on horseback. Severing a line could temporarily disrupt Confederate communications and interfere with the movement of military information.

The reconnaissance party went even further.

A large group of prisoners was captured during the operation, adding another potential source of intelligence while weakening Confederate control in the immediate area.

Throughout the mission, Sullivan remained exposed to the possibility of discovery and attack.

His Medal of Honor citation emphasized not only what the party accomplished but how Sullivan behaved while carrying out his duties. Despite being in immediate danger from enemy forces, he displayed gallantry and coolness throughout the operation.

The intelligence gathered during the two-day reconnaissance provided valuable information about the Confederate defenses protecting Wilmington.

For Union commanders, such knowledge mattered enormously. A successful attack on a fortified harbor required information about waterways, batteries, defensive positions, troop strength, communications, and possible approaches. Sullivan and his companions helped obtain that information at considerable personal risk.

Their mission took place months before the major Union assaults against Fort Fisher, the massive Confederate fortification guarding the entrance to the Cape Fear River.

Those later operations eventually became decisive in closing Wilmington to blockade-running traffic, but intelligence missions such as the one conducted by Sullivan and the Monticello party formed part of the broader effort to understand and penetrate the defensive network protecting the port.

Sullivan’s conduct between June 23 and June 25, 1864, was formally recognized later that year.

Under General Order No. 45, dated December 31, 1864, John Sullivan was awarded the Medal of Honor for his gallantry and coolness during the Wilmington reconnaissance.

The Navy Medal of Honor had been established during the Civil War as the nation’s highest military decoration for extraordinary conduct by sailors and Marines. Sullivan’s award was unusual in that it did not result from manning a gun during a fleet battle or storming a fortification.

His distinction came through reconnaissance.

He entered dangerous territory, helped disrupt enemy communications, participated in the capture of Confederate personnel and mail, and contributed to the collection of vital military intelligence while remaining under constant threat from the enemy.

No clasp, star, or other device accompanied his Medal of Honor.

Sullivan’s broader wartime naval service was later represented by the Navy Civil War Campaign Medal. That decoration commemorated qualifying service by United States Navy and Marine Corps personnel during the Civil War.

For Sullivan, the campaign medal represented his wider participation in the Union naval war, while the Medal of Honor remained specifically tied to the hazardous reconnaissance undertaken from USS Monticello in June 1864.

His Medal of Honor action also demonstrates how varied courage could be during the Civil War.

Some recipients were recognized for capturing enemy flags.

Others remained at their guns under devastating fire, rescued wounded comrades, or led assaults against fortified positions.

John Sullivan’s courage took another form.

For two days and two nights, he carried out a dangerous intelligence mission within reach of Confederate forces.

The sailors could not rely on the protection of their ship’s heavy guns once they had moved into enemy-controlled territory. Discovery could have resulted in capture, injury, or death.

Still, Sullivan remained composed and performed his duties.

He survived the Civil War and lived for nearly half a century after the conflict ended.

John Sullivan died on June 23, 1913, exactly forty-nine years after the opening day of the reconnaissance that had led to his Medal of Honor.

He was buried at Harmony Grove Cemetery in Portsmouth, New Hampshire.

His story remains closely connected to USS Monticello and the struggle for Wilmington.

The mission did not involve a famous charge or a dramatic duel between warships.

Instead, it depended on patience, nerve, secrecy, and the ability to continue operating while surrounded by danger.

A Confederate mail carrier was captured.

Enemy communications were cut.

Prisoners were taken.

Vital information about the defenses of Wilmington was obtained.

Throughout it all, John Sullivan maintained the gallantry and coolness that ultimately earned him the Medal of Honor.

His legacy is that of a Union sailor whose courage was measured not by how loudly he fought, but by how steadily he performed a dangerous mission behind enemy defenses when discovery could have ended it at any moment.