As the Secret Service schemed and plotted in Canada, one of the Confederacy’s most significant missed opportunities of the war began on June 28, 1864, when Jubal Early started marching his army toward the nation’s capital dozens of miles north. With Hunter fleeing to West Virginia, Early’s army had a clear path on the Valley Pike in the Shenandoah Valley and into Maryland. The original objective of Early’s mission was multifold: to draw Union troops away from Grant’s devastating siege of Petersburg, to disrupt the B&O railway lines, to free thousands of Confederates held captive in the Point Lookout prison camp southeast of Washington, DC, and finally to threaten and potentially seize the capital. Early promised Lee on June 28 “to threaten Washington” and, if an opportunity presented itself, “find an opportunity to take it.”1
Early’s march on Washington had its origins weeks earlier. After sustaining massive casualties at the Battle of Cold Harbor on May 31–June 12, Grant—unlike his predecessors, who, after defeat, retreated to Washington—kept marching around Lee’s lines at Richmond to strike the vital railhead at Petersburg some twenty miles south of the Southern capital. The battle unfolded on June 9, when Union forces under General Benjamin Butler attacked Petersburg but failed to seize the town, giving Lee precious time to reinforce and entrench his troops in the area. Over the coming days, Grant moved his army over a pontoon bridge on the James River toward Petersburg. Both sides dug in with trenches that eventually stretched over thirty miles from Richmond to the eastern and southern portions of Petersburg in the Union’s attempt to sever the rail lines into and out of Richmond. Desperate to relieve pressure on Petersburg, Lee dispatched Early to save Lynchburg from Hunter and draw Union troops away from the siege of Petersburg and, if the opportunity presented itself, threaten Washington.
For days Early marched his 14,000-man-strong army north from Lynchburg with almost no resistance. The opportunity to capture the Union’s capital city became a more realistic possibility. Early kept Union authorities guessing on his target: the B&O Railroad, Baltimore, or Washington. Grant knew Early’s force was meant as a distraction and an attempt to bleed off Union troops from his siege at Petersburg. But the distraction proved potentially devastating: Early had an uninhibited path to the capital, its resources, and the president.
On July 6 Captain Robert E. Lee Jr., General Robert E. Lee’s youngest son, arrived in Early’s camp outside Frederick, Maryland, with orders from his father for Early to launch one of the most daring special operations missions of the war: free the prisoners at Point Lookout, some 10,000 men. Initially hatched by Lee in the winter of 1863, the plan accelerated when Lee wrote Davis on June 26 urging, “Great benefit can be drawn from the release of our prisoners at Point Lookout. The number of men employed for this purpose would necessarily be small.… I think the guard might be overpowered, the prisoners liberated and organized, and marched immediately on the route to Washington.”2
Early ordered Marylander brigadier general Bradley Tyler Johnson to head east toward Baltimore, cutting telegraph lines and burning bridges as he went to stall Union communication and troop movements. The former Maryland politician had raised and formed his own company at the beginning of the war and later led plans to form a Maryland Line (regiments composed of Marylanders), and now he commanded his own brigade. Early’s plan then called for Johnson to head south toward Point Lookout on the southeastern side of Washington by the morning of July 12, in time to conduct a simultaneous assault with troops from an amphibious force that included operatives in the Confederate Secret Service sailing up the Chesapeake Bay from Wilmington, North Carolina, carrying thousands of arms for the freed prisoners.
Despite Johnson’s men successfully executing their first objective, multiple events resulted in Jefferson Davis aborting the operation before it fully unfolded on July 12. Johnson took longer than anticipated in his almost impossible task of traveling over 200 miles through enemy territory in such a tight time frame. Davis feared that the Union fleet would destroy the amphibious force at the mouth of the Chesapeake. And finally, details of the operation had leaked out to Union authorities, jeopardizing the entire mission. Had freeing the Confederate prisoners ranked as a higher priority or Johnson been sent on a more direct path, the plan might have succeeded; the impact of thousands of troops to replenish and reinforce Early’s Army of the Valley District could hardly be calculated. In truth, this operation that one Confederate officer referred to as “decidedly the most brilliant idea of the war”3 could probably have moved forward even without the naval component of the plan. Point Lookout’s defenses—the feebly manned Union garrison—could hardly have withstood an onslaught from a brigade of seasoned Confederate veterans while also maintaining control of thousands of angry Southern prisoners.
At the same time as Johnson moved toward Point Lookout, Major Harry Gilmor and his band of roughly 175 men went on a rampage through Union territory to divert their enemy’s attention from the prison break and the attack on the capital. A member of an elite Baltimore family, the dashing Gilmor was imprisoned for his staunch Southern sympathies by the Federal government when the war broke out. After his release, he joined the Confederate Army as a private, although he was quickly promoted to sergeant major and raised his own company, where he earned his reputation as a scout for various Confederate commands. In 1863, he organized the 2nd Maryland Cavalry, also known as “The Band” or Gilmor’s Partisan Raiders,4 who used unconventional tactics to harass Yankee targets, cutting telegraph lines, tearing up track, even burning Maryland governor Augustus Bradford’s summer home in retaliation for Hunter’s burning of the former Virginia governor’s home in Lexington.
In one instance, on July 11, Gilmor used a flaming captured train emptied of passengers from the Philadelphia, Wilmington, and Baltimore Railroad to set a bridge over the Gunpowder River on fire. In addition to destroying the bridge, he also snared a high-value target in passenger Major General William B. Franklin, the commander of XIX Corps. “I backed the whole flaming mass down on the bridge, catching some of the infantry a little way from shore upon the structure and compelling them to jump into the water. The train was running slowly, and stopped right on the draw, where it burned and fell through communicating the fire and destroying the most important part of the bridge.”5 After burning the trestle, Gilmor and his men headed toward Towsontown (presently Towson), where he stopped off at Ady’s Hotel and cavalierly downed a glass of ale. When he received word of a large Union cavalry detachment arriving from Baltimore, he instructed several men to guard their prisoner, General Franklin, and several Union officers. But their captors had passed out from exhaustion and the prisoners slipped away in the dead of night.
Gilmor and his men acted as Early’s scouts as they marched north through the Shenandoah, but when Early tapped the Marylander for the special operations mission, Early and Johnson deprived themselves of one of their best eyes and ears. Old Jube also failed to utilize fully the war’s master spy, John Singleton Mosby, and his Rangers.