His meticulous habits—and protean nature—manifested themselves early on. Waterman was born in New Haven, Connecticut, in 1932, the fifth and last child of a Yale physics professor who later became the first president of the National Science Foundation and moved the family to Washington, D.C. Alan T. Waterman was an old-school Roosevelt liberal and an experienced outdoorsman, and while his political ideas never rubbed off on his son—Guy became a staunch Republican while still a teenager—the two spent many summers canoeing and hiking the great North Woods of Maine and New Hampshire.

But Guy's first true love was the piano, and by the age of 16 he was making a living in the Washington area with the Riverboat Trio, a ragtime band. And there was another leading passion: At just 18, over his father's objections, Guy married his high school sweetheart. By the time he graduated from George Washington University three years later, Guy and Emily Waterman had two sons and a third on the way.

After college, Waterman left music behind to enter politics, first as a legislative aide for the Senate Minority Policy Committeeand then as a speechwriter for President Dwight Eisenhower, Vice-President Richard Nixon, and Michigan Congressman Gerald Ford, among others. By all accounts, he was destined for a promising career on Capitol Hill. But after Nixon lost to Kennedy in the 1960 presidential election, Waterman moved his family to Stamford, Connecticut, and began a new career as a speechwriter and labor negotiator for General Electric. "Corporate life was an odd fit for Guy," says Mike Young, a New Hampshire physician and climber who met the Watermans in 1973 and had heard Guy talk of his days as an organization man. "He said he never went out to lunch with the guys from the office. Instead he'd walk around the streets of Manhattan and sit down with a peanut butter and jelly sandwich and Milton's Paradise Lost." According to Young, Waterman memorized eight and a half of the 12 books of that epic poem—nearly six hours of blank verse.

It was another book—The Climb Up To Hell, an account of a tragic climb in 1957 on the Eiger's northwest wall—that turned Waterman's thoughts back to the outdoors. He joined the New York chapter of the AMC and, in 1963, learned to rock climb upstate in the Shawangunks. Three years later, accompanied by the family dog, Waterman and his two eldest sons, Bill and Johnny, by then teenagers, would blitz New Hampshire's 46 highest mountains in a record 14 days. (Since then, two additional 4,000-foot-plus peaks have been charted in New Hampshire.)

As the lure of the mountains intensified, Waterman grew weary of life as a corporate exec and suburban family man. On top of that, his marriage had begun to unravel. In 1969, he and his wife separated; they were divorced two years later. (Citing a desire to protect her privacy, family members politely refused to help me contact Emily Waterman for this story.) "I think Guy always felt that getting married so young had been a mistake," Young says.