Kilpatrick’s Raid on Richmond: Doomed to Failure? 
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Kilpatrick’s Raid on Richmond: Doomed to Failure? 

Civil War

Kilpatrick’s Raid on Richmond: Doomed to Failure? 

Historians are always in argument over how General Kilpatrick’s raid on Richmond had failed, but how did it come about? Read more about it inside.

Historians are always in argument over how General Kilpatrick’s raid on Richmond had failed, but how did it come about? Read more about it inside.

by Arnold Blumberg

In mid-winter 1864, Union Brig. Gen. Judson Kilpatrick had a bright idea. The chief of the 3rd Cavalry Division, Army of the Potomac, had seen newspaper accounts of an aborted attempt to release Union prisoners of war held in and near Richmond, Virginia, the Confederate capital. Kilpatrick was convinced he could succeed where others had failed. Others were not so sure. Even his nickname, “Kill-Cavalry,” referring to his careless handling of the troops under his command, did not inspire confidence.

Crazy Bet’s Master Plan

The original idea for the rescue mission was broached by Elizabeth Van Lew, a member of a prominent Richmond family who was not only a Northern sympathizer but also a self-appointed spy. To hide her espionage activities, she took on the character of a demented woman, thus earning her the unflattering nickname “Crazy Bet.” Van Lew brought the idea to Maj. Gen. Benjamin Butler, commander of the Army of the James, stationed at Fortress Monroe on the Virginia Peninsula. She provided Butler with detailed information concerning the number and location of Union captives in and around Richmond. There were more than 1,000 officers in the Libby Warehouse, 6,300 enlisted men at Belle Isle, and 4,300 others scattered around the city in smaller buildings.

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After securing the promise of a diversionary move by elements of the Army of the Potomac along the Rapidan River in northern Virginia, Butler directed his subordinate, Brig. Gen. Isaac J. Wistar, to lead 4,000 infantry and 2,200 cavalry straight up the Peninsula to Richmond. Secrecy and surprise were vital to the success of the mission. Moving out on the morning of February 6, the force reached Bottom’s Bridge, 12 miles east of the Southern capital, the next day. There, the Federals found their path blocked by strong Confederate forces. The raid had been exposed by William Boyle, a Union soldier whose death sentence for murdering a superior officer had been set aside and who had then escaped to the South and revealed details of the raid.

After a weak-hearted assault on Bottom’s Bridge, Wistar took his troops back to Fortress Monroe. The Butler raid ended in a well-publicized fiasco. Although Butler and the administration of President Abraham Lincoln were chagrined and embarrassed by the episode, Kilpatrick saw the failure as a golden opportunity. In late January 1864, the young cavalry general told Michigan Senator Jacob Howard that he was prepared to lead another assault on Richmond to free Union prisoners. As Kilpatrick hoped, his scheme reached the notice of the White House. On February 11, Maj. Gen. John Sedgwick, temporarily commanding the Army of the Potomac, ordered Kilpatrick to report to Washington and present his proposal in person to President Lincoln.

Getting Lincoln’s Approval

The next day, the general met with Lincoln—it was the president’s 52nd birthday—and Lincoln asked if it would be possible during the raid for Kilpatrick to distribute the government’s amnesty offer granting pardons to all Southerners who took an oath of alliance to the United States. Kilpatrick assured the president that would be a priority, thus gaining Lincoln’s instant approval for his foray. Four days later, Kilpatrick submitted a formal proposal.

The plan called for a force of 3,600 cavalry accompanied by six cannons to cross the Rapidan River at Ely’s Ford and head for Spotsylvania Court House. The expedition would carry five days’ rations and dispense with supply wagons, the idea being that the marauders would move rapidly and live off the land. After arriving at Spotsylvania, the strike force would split into two groups: 500 men would proceed to Frederick’s Hall, ripping up as much of the Virginia Central Railroad as they could along the way, then move south to the James River. Once there, they would destroy the James River & Kanawha Canal above Richmond, then cross to the south side of the river doing as much damage to the Richmond & Danville and Richmond & Petersburg Railroads as possible. Finally, they would rush into Richmond from the south while Kilpatrick and the main body of troops assailed the city from the north.

Once inside Richmond, Kilpatrick would free all the Federal prisoners and arrest Confederate President Jefferson Davis. Kilpatrick gave himself the option of returning the way he had come or riding to join Butler’s army on the Peninsula. Kilpatrick’s plan depended on two diversionary moves by friendly forces: first, a thrust by Butler at Richmond to draw Confederate forces from the city; and second, a cavalry raid toward Charlottesville to keep the gray cavalry of Maj. Gen. J.E.B. Stuart occupied and away from Richmond.

Plans Underway

Although rankled by Kilpatrick going over their heads to the president and convinced that the venture would turn out poorly, Maj. Gen. George Gordon Meade, commander of the Army of the Potomac and Kilpatrick’s immediate superior, and Maj. Gen. Alfred Pleasonton, chief of the Cavalry Corps, cut the appropriate orders for the raid’s execution. At the same time, Colonel Ulric Dahlgren, the 21-year-old son of Union Admiral John A. Dahlgren, joined the venture, assuming command of the force that would cross the James River. Dahlgren had just returned to active duty after losing a leg at Hagerstown, Maryland, during the Battle of Gettysburg campaign, and it is not unlikely that the White House pressured Kilpatrick to include him in the raid. It is also likely that Kilpatrick saw the value in having a politically well-connected ally—and potential scapegoat—on board.

At 5:20 pm on February 28, 3,600 handpicked troopers from 15 regiments of the Cavalry Corps moved out of Stevensburg, Virginia. In the lead rode Dahlgren’s advance guard, numbering about 460 men. The main body of horsemen followed. Behind them were a number of Army ambulances carrying land mines (called torpedoes) and copies of Lincoln’s amnesty proclamation. Bringing up the rear was Captain Dunbar Ransom’s Battery C, 3rd U.S. Artillery, which was equipped with six 3-inch rifled guns. A Pennsylvania officer summed up the feelings of the participants at the time: “Everybody was in excellent humor, for nothing delights the heart of a cavalryman as to go on a scout or a raid.”

 

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