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There's an anecdote regarding his Civil War days that goes like this:
"Grant is a drunkard," asserted powerful and influential politicians to the President at the White House time after time; "he is not himself half the time; he can't be relied upon, and it is a shame to have such a man in command of an army."
"So Grant gets drunk, does he?" queried Lincoln, addressing himself to one of the particularly active detractors of the soldier, who, at that period, was inflicting heavy damage upon the Confederates.
"Yes, he does, and I can prove it," was the reply.
"Well," returned Lincoln, with the faintest suspicion of a twinkle in his eye, "you needn't waste your time getting proof; you just find out, to oblige me, what brand of whiskey Grant drinks, because I want to send a barrel of it to each one of my generals."
It is likely Grant is commemorated on the $50 because of his status as the commander of the Union Army during the Civil War. He was also the first three-star general since Washington. Despite his failed presidency, in which his cabinet was beset by graft and cronyism, he himself was oblivious to it, or at least impotent in the face of it, and taken advantage of because of his trusting nature. He wasn't crooked himself, but his administration was unfortunately deep into it. He went into office determined to advance civil rights, and in fact some very important amendments to the Constitution were ratified during his tenure... but his idealism was stunted by his inability to control the graft going on under his watch. Few presidencies had as much unfulfilled promises and dashed expectations during his two terms in office as did Ulysses Grant.
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