This secret Civil War sabotage mission was doomed from the start

When George Davenport Wilson and Philip Gephardt Shadrach volunteered for a secret Civil War mission in 1862, they knew it was going to be dangerous.

The Union privates were among the nearly two dozen operatives tasked with sneaking behind enemy lines to commandeer a locomotive that they would then ride to the Rebel stronghold of Chattanooga, Tennessee—tearing up rail lines, cutting telegraph wires, and burning bridges behind them as they went.

The odds were stacked against them. They could be shot at by Confederate forces trying to prevent this destruction to Southern infrastructure. If captured, the Union volunteers would most likely be executed as spies since they were wearing civilian clothes.

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Known today as the Great Locomotive Chase, this perilous mission would go down in in U.S. Army history as one of the original Special Ops missions. Its participants would become the first recipients of the newly created Medal of Honor for military service members who go “above and beyond the call of duty.”

Except for Wilson and Shadrach. For unknown reasons, these were overlooked until this summer when their descendants were finally presented Medals of Honor at a White House ceremony.

But while the men who took part in the Great Locomotive Chase have gone down as heroes, their mission wasn’t quite the success that they had hoped. “It looked much better on paper, than I afterwards found it on land,” William J. Knight, one of the volunteers, later said.

Assembling the squad

“This is a war story, but it also a great adventure story,” says Russell S. Bonds, author of 2006’s Stealing the General: The Great Locomotive Chase and the First Medal of Honor. “To me, it’s The Great Train Robbery, The Great Escape, and The Dirty Dozen all rolled up into one.”

The plan was conceived by civilian scout and Union spy James J. Andrews as part of a larger plot to capture Chattanooga—which would cut the South in two and might end the war early. Because the major rail hub could be easily reinforced from Atlanta, it was important to sever rail lines to prevent additional Confederate troops from arriving.

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Andrews had just returned from the South after an earlier attempt to hijack a steam locomotive, which was aborted when the engineer failed to arrive. For the second operation, he selected one civilian and 22 soldiers—now known as Andrews Raiders—several of whom knew how to operate a train.

None of the men from the first mission agreed to go this time. When one heard about the second attempt, he replied, “(Andrews) would fool around with that scheme until he got hanged.”

Despite the dangers, the volunteers were excited. Corporal William Pittenger admitted to being “tired … of the dull monotony of army life” and wanted to do something “ambitious and patriotic.” In his 1889 book, he wrote, “If it was possible to do more for the country by a little extra risk, I was more than willing to assume it.”

Andrews was frank about the mission’s perils: “You are soon to enter upon our dangerous duty, but the first man that gets drunk, or flinches in the least, I will shoot dead on the spot; your objective must be accomplished, or you must leave your bones in Dixie.”

While Andrews Raiders prepared for their mission, Union General Ormsby Mitchel readied his 10,000-man Army of the Ohio for battle on Chattanooga.

A doomed mission

In small squads, the volunteers secretly made their way to the Georgia town of Big Shanty (now Kennesaw), about 95 miles south of Chattanooga. At about 5 a.m. on April 12, Andrews and 20 raiders boarded a locomotive nicknamed the General, uncoupling passenger cars but keeping the tender and three boxcars.

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Around 14 miles north of Big Shanty, the General stopped at an iron works. There, on a siding, Knight spotted another locomotive, Yonah—with steam up and ready to run.

“We ought to disable her and burn the bridge,” he said to Andrews, who dismissed the idea. It was a big mistake. Moments after the Yankees departed, Confederate chasers arrived on a handcar and then followed in hot pursuit on the awaiting locomotive.

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The trains raced at breakneck speeds over the next 90 miles of straight track. Along the way, Andrews Raiders avoided capture by bluffing Southern agents at each station and refueling stop, claiming to carry relief supplies for Confederate forces.

However, the Union operatives had a difficult time carrying out the rest of their objectives. Heavy rain had soaked the wooden trestles of the bridges they passed, making it impossible to set them ablaze. They lacked both the equipment and time to destroy telegraph lines and railroad tracks. In fact, they had almost no training for the dangerous tasks assigned to them.

“They had no tools, few weapons, and little idea of what was expected of them,” says Shane Makowicki, historical studies directorate at the U.S. Army Center of Military History. “Today, Special Ops teams undergo extensive training for weeks or months before beginning a mission.”

Finally, it was the end of the line for Andrews Raiders. They ran out of wood and water to power the locomotive about 18 miles from Chattanooga and scattered into the countryside. Meanwhile, General Mitchel and the Army of the Ohio had failed to take the Rebel city, leaving the Union men stranded.

A lasting legacy

“In Civil War studies, the Great Locomotive Chase is often regarded as a footnote because it was a failure,” Makowicki says.  Maybe so, but the daringness of the mission and excitement of the train ride have left a cultural impact that still resonates more than 160 years later. Movies, books and more continue to capture the interest of the public today.

All of the men who had commandeered the train were captured within two weeks. They were found guilty by Confederate courts-martial as spies and were sentenced “to be immediately hung by the neck until dead.”

Andrews was executed June 7, 1862. Seven other men were hung 11 days later. “We are here to die as Union soldiers, who undertook to do in one day, that which will cost the country millions of dollars and thousands of lives to accomplish in years,” Wilson prophetically announced from the gallows.

Rather than await their fate, the remaining raiders escaped. Eight made it back to Union lines. Six were recaptured but were eventually paroled in a prisoner exchange.

On March 25, 1863, six of the raiders met with Secretary of War Edwin Stanton in Washington, D.C. He presented them with Medals of Honor, which had recently been approved by Congress. The men were then taken to the White House, where they shook hands with President Abraham Lincoln. “We left him, exceedingly proud of the honor the greatest man in the nation (or world) had conferred upon us,” Pittenger later wrote.

Over the decades, all Andrews Raiders received Medals of Honor. But why did it take so long for Wilson and Shadrach?

“No one knows why for sure,” Bonds says. “Early on, the Medal of Honor was awarded usually after someone advocated for the man. In the case of Wilson and Shadrach, it appears no one spoke up for them.”

That mistake was corrected on July 3, when President Joe Biden presented Medals of Honors to descendants of the two men at a White House ceremony.

Some members of the team have still gone unrecognized: Andrews and fellow civilian William Campbell are not eligible for the Army awards. Some historians believe they should receive the Presidential Medal of Freedom for their sacrifices instead—despite the poor planning and missed opportunities that led to a tragic failure.

“It was a very bold and masterful idea that was undone by slipshod execution,” Bonds says. “Many events conspired against them, including the weather, pressure from behind and bad luck. It was undertaken by Ohio farmers, mechanics and carpenters who didn’t know enough to be scared. “It demonstrated how small units can have great impact in a theater of war.”