The men of the 54th trained near Boston at Readville, under the constant scrutiny of white soldiers, many of whom believed black soldiers lacked the stomach for combat. Yet the negative perceptions seemed only to inspire a sense of unity within the ranks of the regiment and their white officers.

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Contrary to recruitment promises, the soldiers of the 54th were paid only $10.00 per month, $3.00 less than the white troops. Shaw had become so committed to his men that he wrote to Governor Andrew, insisting that his entire regiment, including white officers, would refuse pay until his soldiers were "given the same payment as all the other Massachusetts troops." Yet Congress did not enact legislation granting equal pay to black soldiers until June 15, 1864.

Shortly after the 54th was mustered into service, the Confederate Congress passed an act stating its intention to "put to death," if captured, "any Negro" as well as "white commissioned officer [who] shall command, prepare or aid Negroes in arms against the Confederate States." The directive only served to strengthen the resolve of the black soldiers.

On May 18 Governor Andrew traveled to the camp to present Shaw with the regimental flags. He made the trip with 3,000 other visitors, including such prominent abolitionists as Frederick Douglass, William Lloyd Garrison, and Wendell Phillips. Douglass had a strong personal link with the 54th–two of his sons, Lewis and Charles, had joined the unit. Andrew presented the flags to Shaw. "I know not, Mr. Commander, in all human history, to any given thousand men in arms, has there been committed a work at once so proud, so precious, so full of hope and glory as the work committed to you," the governor said.

Ten days later the 54th Regiment of Massachusetts Volunteer Infantry marched through the streets of downtown Boston, greeted by the cheers of thousands who assembled to see them off at Battery Wharf. It was an impressive spectacle. Shaw, atop his chestnut brown horse, led the way. Close behind marched the color bearers, followed by young black soldiers, handsomely clad in their sharp, new uniforms.

The dress parade gradually made its way to the wharf and boarded the De Molay bound for Port Royal Island, South Carolina. There the regiment reported to the Department of the South. Once the men arrived, however, reality set in when they were relegated to manual labor. Not until June 8, when Shaw and his men joined Colonel James Montgomery and the black troops of his 2nd South Carolina Colored Volunteers on an "expedition" to Georgia, did they see any action, and that was during a pointless raid on the small town of Darien. After plundering the 100 or so residences, three churches, the market-house, courthouse, and an academy, Montgomery ordered Darien set afire. Begrudgingly, Shaw directed one of his companies to torch the town. Fanned by a high wind, the flames eventually destroyed everything but a church and a few houses.

Afterward, Shaw wrote to Lieutenant Colonel Charles G. Halpine, the acting adjutant general of the department, to condemn this "barbarous sort of warfare." Shaw knew his complaint could result in his arrest or even court-martial, but he felt compelled to express his feelings. He later learned that Montgomery had acted in accordance with the orders of his superior officer, General David Hunter. Soon after the Darien raid, President Lincoln relieved Hunter of his command.

The sacking of Darien and the manual labor his troops were compelled to do disheartened Shaw. "Our whole experience, so far, has been in loading and discharging vessels," he wrote to Brigadier General George C. Strong, commander of Montgomery’s brigade. "Colored soldiers should be associated as much as possible with the white troops, in order that they may have other witnesses besides their own officers to what they are capable of doing." That opportunity finally arrived on the morning of July 16, 1863. Fighting alongside white troops on James Island, Shaw’s men acquitted themselves well in a sharp skirmish. That same night they ferried to Morris Island, where battle lines had already been drawn for the anticipated attack on Fort Wagner. Despite their exhaustion, hunger, and wet clothes, the men of the 54th were determined to fight on.

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