Ol' What's'is ('er) Name... #1

Hiram Ulysses Grant, later known as Ulysses S. Grant, because of a military clerical error.

Born in the Midwest to a modest, hard working family.
He attended religious schools in both Kentucky and Ohio.
An average student, he graduated college ranked 21st in a class of 39.
He took a Commission as an Officer in the Army, and twice received commendations for bravery, but later told a friend he thought the U.S. had waged a "wicked war".
Assigned duty on the West coast, he was miserable and took to drinking heavily and was forced to resign.
He had reached the rank of Captain.

Prior to leaving the Army he married.
As a civilian, he bought 80 acres of land, intending to clear and farm it.
Two years later, he was in such terrible financial straits he had to pawn family heirlooms in order to buy Christmas presents for his kids.

Tensions mount and his services are again needed by the Army, so he joins, and is quite successful.
He's so successful as a soldier, he parlays his military success into winning election as a politician, but almost immediately following his election, a financial disaster strikes the U.S.
Although never found to be dishonest himself, he has surrounded himself with scoundrels, and some call his political world (I'm paraphrasing here), "the most corrupt ever seen in U.S. politics."