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Spiro T. Agnew
Sure, it's bad to be remembered as an evil and corrupt politician. But what's really bad is to be remembered as a mediocre evil and corrupt politician. In all fairness, Spiro T. Agnew really never had a chance. You don't put your kid on the path to greatness by naming him "Spiro." Long before Michael Dukakis made it unfashionable, Agnew was the son of Greek immigrants. On the bright side, he looked more at home in a tank. He served in the Army in World War II, a company commander in an armored division, with actual fighting and everything, and he reupped for a year in Korea. After the military, Agnew became a lawyer in his home town of Baltimore. He took an interest in politics, first becoming involved at the county level, then running for governor of Maryland in 1966. This was not as big a leap as it might sound, since Maryland is pretty much all Baltimore, but still, progress is progress. Agnew beat his conservative Democratic candidate on a platform of relative liberalism. As governor, Agnew was a fairly moderate guy, initiating programs to assist the needy, a sliding-scale income tax, and open housing laws. He also instituted programs to assist needy governors of Maryland named Spiro Agnew. As governor, Agnew took kickbacks from major contractors in Maryland, although he never, ever, EVER admitted that. The payments, which Agnew forever insisted were legitimate campaign contributions, came in small bills in unmarked envelopes, totaling at the minimum some $200,000 plus. In 1968, no one really was talking about this retirement plan however. When uncharismatic, uninspired, evil presidential candidate Richard M. Nixon decided to blaze a trail back into national politics over the corpse of John F. Kennedy in 1968, he needed a very special individual as his running mate.
Agnew was sent out on the campaign trail, and later as vice president, to attack the hippies, leftists and pinkos that Nixon felt were primarily responsible for the decline of America (which couldn't possibly have been his fault). Armed with a series of ad hominem zingers penned by Nixon's sleaze purveyors Pat Buchanan and William Safire, Agnew made many memorable contributions to the history of destructo-politics with gems like these:
Needless to say, these shitbombs of malicious nonsense didn't exactly endear Agnew to the young people, or just about anyone else either. Agnew quickly went from small-time politico to national punchline. The image of "buffoon" was rarely invoked so easily as by mentioning Agnew's name, although he commented in an interview once that his attack-dog role was the most "virile" of his vice presidential duties. Everyone knows how the story of the Nixon administration turned out, of course, and Agnew was one of its first casualties. As Watergate relentlessly worked its way into the national vocabulary, Agnew's Maryland kickbacks suddenly took on a very high profile and new charges surfaced that he was still taking bribes as vice president. Agnew called the allegations of bribery "damned lies" and vowed never to resign the vice presidency. Then he resigned. OK, maybe it wasn't quite as abrupt as all that, but it was close. Agnew stepped down on Oct. 10, 1973, just under a year before his boss would do the same. Unlike Nixon, Agnew had to face the music. Sort of. This was, after all, only the beginning of the modern era of criminal presidencies, and at the time, there wasn't a huge zest for dragging the secondmost powerful man in American politics through the gutters.
Agnew was fined a measly $10,000, sentenced to three years probation and disbarred. A later civil suit ordered him to make nearly $300,000 restitution to the state of Maryland. After the vice presidency, Agnew wallowed in self-righteous dudgeon for a while, penning a mean-spirited but utterly non-titillating autobiography called "Go Quietly... Or Else," in which he unsuccessfully tried to portray himself as a victim of the Nixon administration's other foibles. He worked the rest of his life as a "business consultant" which is political code for "he was taken care of by his former political patrons," and died in 1996 at the age of 77. Had he lived just a little while longer, he would have enjoyed the grim satisfaction of watching Bill Clinton get impeached for Oral Sex. No doubt, he would have been welcomed back to the fold as a talking head on TV news programs, perhaps winning belatedly the pity that he so badly wanted but never really deserved.
Fun fact! The letters Spiro Agnew may be rearranged to spell grow a penis. This is surely no coincidence. Bribery allegationsInterview with Lester Matz (Justice Department transcript):
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Nixon picked Agnew, the liberal governor of a small state, and transformed him into an arch-conservative attack dog the likes of which the nation had not seen since... Well, since Richard Nixon. 
"A Nixon-Agnew administration will abolish the credibility gap and reestablish the truth — the whole truth — as its policy."
On the same day he stepped down, Agnew copped a "no contest" plea to charges of tax evasion, which basically means admitting you have done nothing wrong except that you're pretty sure you would get convicted by a jury of your peers. (The tax evasion charge always cracks me up, whether it's