He suffered a wound in his right leg in a cavalry skirmish following the Battle of Gettysburg and lost the limb below the knee to amputation. The still-recuperating Dahlgren, now fitted with a wooden leg and using a crutch, possessed no command experience when he appeared at Kilpatrick’s headquarters in the third week of February 1864 to ask for a job. Yet, the job he received was nothing less than command of the select contingent slated to break into Richmond and liberate the prisoners–and, as it proved, to carry out certain highly secret tasks as well.

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Young Dahlgren was known to have friends in high places, including the White House, and that no doubt influenced Kilpatrick’s decision. But Kill-Cavalry also probably liked the fact that Dahlgren was, militarily speaking, an outsider. Kilpatrick would be operating with a secret agenda for his Richmond raid, and he required a like-minded subordinate to help him execute it. All of the Cavalry Corps’ colonels who were eligible for command roles in the expedition were either Regulars or, if volunteers, were veteran leaders familiar with what passed for the rules of civilized warfare. Kilpatrick was going to break those rules, and he read in Ulric Dahlgren someone who would have no qualms about also breaking them. On the eve of the raid, and fully briefed on the secret role he was to play, Dahlgren wrote his father a letter that reflected not qualms but only exuberance: ‘there is a grand raid to be made, and I am to have a very important command. If successful, it will be the grandest thing on record; and if it fails, many of us will ‘go up‘…but it is an undertaking that if I were not in, I should be ashamed to show my face again.’⁷

Another important participant in the Kilpatrick-Dahlgren raid–important, too, in later confirming the authenticity of the Dahlgren papers–was the Bureau of Military Information. This highly capable military intelligence unit had been founded by Colonel George H. Sharpe a year earlier, and by 1864 its expert staff was working in close harness with the Army of the Potomac. A BMI spy in Richmond furnished Kilpatrick with data on the city’s defenses. Captain John C. Babcock, the BMI’s liaison officer at Meade’s headquarters, pinpointed Confederate positions and strengths and supplied Dahlgren with a guide for his part of the mission. Captain John McEntee, Sharpe’s second in command, led a BMI party that rode with the Dahlgren raiders. It appears that McEntee was the only officer whom Dahlgren treated as a confidant, for he told him of his secret orders.⁸

After all the high-level planning and preparation, the execution of the Kilpatrick-Dahlgren raid came as a decided anticlimax. Early on February 28, under cover of an infantry and cavalry diversion that Meade launched westward around Lee’s left flank, Kilpatrick and Dahlgren led some thirty-six hundred troopers across the Rapidan River and past Lee’s right to begin their ride south toward Richmond.

The next day Dahlgren left the main column and started his contingent of 460 men on a wide swing to the west, aiming to strike the James River some twenty-five miles above Richmond. The plan called for him to cross the James at this point and proceed along its south bank and then push through the capital’s largely undefended southern portals. It was believed he could easily break into the city there and free the prisoners in Libby Prison and on Belle Isle.

Kilpatrick, meanwhile, would strike at the northern environs of the city. Depending upon circumstances, he would either break in to join Dahlgren or divert the defenders so Dahlgren might carry out his mission unopposed. According to the directive for the mission, the raiders would then leave the city with their liberated prisoners, turn eastward, and hasten down the Peninsula to gain a haven behind Ben Butler’s Army of the James.

Nothing went according to plan. Dahlgren discovered the James was running too high from the winter rains to cross. In a fit of particular savagery he turned on his guide, a black freedman supplied and vouched for by the BMI’s John Babcock, and had the man hanged from a tree on the riverbank. Proceeding toward Richmond but on the northern side of the James, Dahlgren soon ran into the city’s militia defenders. With that he gave up on his mission and turned away to the north in an effort to rejoin Kilpatrick.

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