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In the Senate, Wilson was compared somewhat unfavorably to the other Massachusetts Republican Senator, Charles Sumner. Sumner was a powerful, eloquent orator with great dignity. Wilson spoke plainly and without emotion. In summing up Wilson, one observer said, “He was not learned, he was not eloquent, he was not logical in a high sense, he was not always consistent in his political actions, and yet he gained the confidence of the people, and he retained it to the end of his life. His success may have been due in part to the circumstance that he was not far removed from the mass of the people in the particulars named, and that he acted in a period when fidelity to the cause of freedom and activity in its promotion satisfied the public demand.” He and Sumner, both strongly opposed to slavery, worked together very well. Even when others distrusted his political maneuvering, they always gave him credit for the sincerity of his opposition to slavery.
At the start of the Civil War, Wilson was very active in the preparations for war. After resigning his commission as colonel and commanding officer of the 22nd Massachusetts, he served as a volunteer aide-de-camp to General George McClellan, commander of the Army of the Potomac. When he reported to camp, he was ordered to accompany other officers on a tour of inspection on horseback of the defenses of Washington. In the words of Benjamin Perley Poore, a Boston newspaper reporter, “Unaccustomed to horsemanship, the ride of thirty miles was too much for the Senator, who kept his bed for a week, and then resigned his position.” Radical Republicans established the Joint Committee on the Conduct of the War, partly because Wilson, as chairman of the Military Affairs Committee, was not radical enough. Wilson at first defended the army, but eventually became just as discouraged and impatient at the slow progress of the war as other Radicals. He, unlike the other Radical Republicans however, never criticized specific generals or military operations. Still, Wilson was one of the inner circle of Radical Republicans. It was Wilson who introduced bills to end slavery in the District of Columbia, to permit blacks to serve in the army, and to give black soldiers pay equal to white soldiers. Wilson also pressured President Lincoln to issue the Emancipation Proclamation, and came out in favor of Lincoln withdrawing from the Republican ticket in 1864 rather than running for re-election.
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