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Having kept his signature buzz-cut through high school (and way beyond), H.R. Haldeman was a straight-arrow and Eagle Scout during his teen years. He joined the Naval Reserve in WWII, but didn't see combat. After the war, he attended UCLA, where he'd meet his eventual close friend and partner in crime John Ehrlichman.
After graduating from UCLA, Haldeman became a Mad Man at a major New York advertising agency, a skill set that would come in handy later in revamping Richard Nixon's public image during the 1968 Presidential campaign (source). He'd admired Nixon's anticommunist work on the House Un-American Activities Committee during the Red Scare years, and his family's longtime support of the Republican Party motivated him to work in Nixon's 1956 and 1960 campaigns. His father was one of the wealthy contributors to an expense fund that nearly ended Nixon's career and prompted Nixon to take to the airwaves for his famous "Checkers" speech (source).
When Nixon was elected President in 1968, he chose the loyal Haldeman for his chief of staff. Haldeman's brusque manner and preoccupation with detail earned him the nickname "the Prussian," and he was described as "having a gaze that would freeze Medusa" (source).
Not a guy you'd want to mess with.
During his career in the White House, Haldeman kept records of his meetings, which were later published as The Haldeman Diaries after his death in 1993. Ehrlichman and Haldeman's roles as Nixon's most zealous and trusted advisors during his administration got them nicknamed "The Berlin Wall" because of their efforts to shield the president from hearing bad news or making bad choices. Haldeman was part the Watergate cover-up from the start and was a target of investigation by the special prosecutor. The mysterious 18 ½-minute gap found on one of the Watergate tapes was part of a conversation between Haldeman and Nixon.
After the Supreme Court decided U.S. v. Nixon, the so-called "smoking gun" tape revealed a discussion between Nixon and Haldeman in which Nixon suggested getting the CIA to pressure the FBI to butt out of the investigation. Haldeman was toast even before that, and he resigned on April 30th, 1973. For his role in Watergate and other offenses, he was convicted of conspiracy and obstruction of justice, and served eighteen months of a 2 ½-to-8-year sentence in federal prison.
Though Nixon said he loved him like a brother, he refused to pardon him.
After his release from prison, Haldeman became a successful businessman, mellowed out, wrote his autobiography The Ends of Power, and finally got a normal haircut. In the book, he claimed that Nixon was in on the Watergate break-in from the start, and suggested that elements of Watergate were linked to the assassination of President Kennedy. He regretted contributing to the pressure-cooker atmosphere in the White House that led to the cover-up, but insisted that the media inflated his importance in Watergate and unfairly painted him as a monster.
After refusing medical treatments because of his Christian Science beliefs, Haldeman died of cancer on November 12th, 1993. Loyal to the end, even having gone to prison for the cause, he described his work in the Nixon White House as the "mountaintop experience" of his life. (Source)