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Even the best of spies–as Timothy Webster discovered–can find themselves holding a losing hand.

When Indiana Sergeant Thomas Harter jumped into the Rapidan River and swam back toward Union lines to warn Major General John Pope of the mortal danger his army faced, he knew full well the risks he was running. Spying was a game played for the highest stakes, and losers seldom got a second chance to play. Harter was lucky, or a good spy, or both. But even good spies sometimes got caught. Take, for instance, Timothy Webster.

Webster, a transplanted Englishman, was Union spymaster Allan Pinkerton’s right-hand man. A former New York City policeman turned railroad detective, Webster moved smoothly into the role of spy at the outset of the Civil War. It was a role he was born to play. His usually hard-bitten mentor positively gushed when describing Webster’s ability. “In a lifetime of varied detective experience, I never met one who could more readily and agreeably adapt himself to circumstances,” said Pinkerton. “No danger was too great for him….”

When rumors swirled that Maryland-based “roughs and secessionists” were planning to murder President-elect Abraham Lincoln as he passed through the state en route to his inauguration, Webster infiltrated a group of conspirators at Perryman and managed to get word to Pinkerton of a plot to kill Lincoln, disrupt railroad and telegraph traffic to Washington, and throw the nation into a panic. Duly warned, Pinkerton spirited Lincoln into the capital ahead of the would-be assassins and averted an immediate crisis.

In May 1861, Maj. Gen. George B. McClellan (who knew Pinkerton from his days as a railroad president before the war) asked the detective to provide “observations made within rebel lines.” Pinkerton turned immediately to Webster, who traveled incognito to Memphis, where he made friends with Confederate officers and even received a guided tour of the city’s defenses. Said an admiring Pinkerton: “He partook of soldiers’ fare in the rebel camp, shook hands warmly with raw recruits, joked and laughed with petty officers, became familiar with colonels and captains, and talked profoundly with brigadier generals. Webster’s talent in sustaining a role of this kind amounted to positive genius, and it was this that forced me to admire the man as sincerely as I prized his services.”

Dodging self-appointed “safety committee members,” Webster traveled by train through Mississippi and Tennessee, pumping fellow travelers for information, and crossed Kentucky to Cincinnati, where he gave Pinkerton a full report.

In the months to come, Webster got himself initiated into the shadowy Knights of Liberty organization in Baltimore. The Knights were planning, they said, to lead an army of 10,000 pro-Confederate Marylanders in an attack on Washington. Once again, Webster got word to Pinkerton, who arranged to have Webster arrested with other leaders to preserve his cover.

Moving south to Richmond, Webster turned his charms on Confederate Secretary of War Judah P. Benjamin, obtaining from him a secret commission to carry messages to Rebel agents in Washington. This led directly to the unmasking of a Confederate spy in the provost marshal’s office in the Union capital.

But Webster’s luck ran out in January 1862. Stricken by a sudden attack of rheumatism, he fell out of sight for several weeks. Fearing the worst, Pinkerton made the mistake of sending two of his other operatives, Price Lewis and John Scully, to Richmond to find Webster. They quickly located him, bedridden at the Monumental Hotel. Suspicious Confederate agents began tailing the two, and they were eventually recognized and arrested as Union spies. Sentenced to hang, the men broke down and betrayed Webster. He was still so ill that when he was brought to jail, a fellow prisoner exclaimed: “My God! They will send the dead here next!”

In a sense, that was what the authorities had done. Webster was a major embarrassment to the Confederate government, Judah Benjamin in particular, and he was convicted and sentenced to death. A distraught Pinkerton implored President Lincoln to intercede, and Lincoln warned the government in Richmond that he would start hanging Southern spies if Webster was killed. At the same time, Secretary of War Edwin Stanton and General McClellan made appeals through diplomatic channels. But it was to no avail.

On April 29, 1862, Webster was taken to Camp Lee, on the old Richmond fairgrounds, and placed on the scaffold. Still crippled by rheumatism, he was fitted with a hood and the trapdoor was sprung. Webster fell to the ground stunned–the noose had slipped off–and murmured, “I suffer a double death.” The noose was then refitted so tightly that Webster complained, “You will choke me to death this time.” He was wrong; the noose held, and Webster became the first American to be hanged as a spy since Nathan Hale in the Revolutionary War. Spying is a dangerous game.

Roy Morris, Jr., Editor, America’s Civil War