Former Virginia senator Jim Webb, the latest White House hopeful to enter the Democratic nomination race and challenge 2016 frontrunner Hillary Clinton, would seem at first blush an attractive candidate for Leader of the Free World.

A centrist Democrat and economic populist, Webb, 69, served a single six-year term in the Senate during George W. Bush’s and Barack Obama’s presidencies before leaving politics to think and write; he was a member of the Armed Services and Foreign Relations committees and opposed the American military adventures in Iraq, Libya, and elsewhere.

A true citizen-politician, he was also a highly decorated Marine first lieutenant during the Vietnam War—awarded a Navy Cross for heroism in combat—as well as a secretary of the Navy during Ronald Reagan’s administration; and if all that were not enough, Webb is also a critically acclaimed, best-selling author, whose 1978 war novel, Fields of Fire, sold a million copies and was adapted for a Hollywood epic.

And yet.

A little-known recent book by former Pentagon official Chase Untermeyer, Inside Reagan’s Navy, presents Webb as a pugnacious egomaniac with a streak of male chauvinism, a boulder-sized chip on his shoulder, and zero sense of humor about himself.

Untermeyer recounts a session in Webb’s private office, during which the Navy secretary reminisced about a long-ago violent dustup with a ponytailed biker.

“I had him by the hair and was beating his head on the sidewalk when he suddenly went limp on me,” Webb recounted. “Then it came to me: I had killed the fucking son of a bitch, and I would be put on report back at the Academy! So I revived him—whereupon he came to and kicked me in the head about 10 times till I was able to grab his leg... Moral: Show no mercy in a fight.”

In response to the revelations in Untermeyer’s book, a Webb campaign spokesman emailed The Daily Beast on Tuesday: “Senator Webb recalls Mr. Untermeyer as a capable assistant and an engaging conversationalist. As a rule, though, he does not comment on private conversations. In a letter to Sen. Webb dated March 12, 2015--as in his book--Mr. Untermeyer wrote, ‘To my view, you are the outstanding American of my generation.’”

Another anecdote—from a book that was published by the academic Texas A&M University Press in March and has received far less attention than it deserves—documents Webb’s insistence on staging his elaborate 1987 installation ceremony at the U.S. Naval Academy in Annapolis, Maryland, smack-dab in the middle of exam week.

Webb, an Annapolis alum, had briefly taught at the Academy in 1979 as a writer in residence, but was bounced from the faculty after making politically incorrect comments concerning women serving in the military. (He was against it.)

Untermeyer quotes General P.X. Kelley, then commandant of the Marine Corps, as encountering a “Marine-option midshipman” who “pleaded with him to get ‘the coronation of King James’ switched from Exam Week.”

Untermeyer continues: “When P.X. carried this message to Webb, Jim’s eyes narrowed, and he said, ‘Those bastards kept me off the campus of my own alma mater for three years, and I’m going to make them suffer.’”

Of course, “the ‘bastards’ in question were long gone,” Untermeyer writes, “and the sufferers were the poor middies who had to participate in the ceremony. Barbara Kelley [the commandant’s wife] said succinctly: ‘The jackass.’”

Arguably these are not qualities that one would necessarily seek in a future president, although Untermeyer also claims to like and admire Webb.

Joking with Webb’s predecessor John Lehman—a man who did show a sense of humor about himself—Untermeyer claimed to see similarities between the two Navy secretaries. Untermeyer told Lehman that Webb was “a temperamental genius—and we all know what it’s like to live with one of those.”

Untermeyer writes: “Jim loves a fight. But whereas with John, fighting and beating your enemies is sport, with Jim, it’s blood sport.”

Untermeyer, who in a former life was a political reporter for The Houston Chronicle and then an elected state representative in the Texas legislature—and later an administrative assistant to Vice President George H.W. Bush, and U.S. ambassador to Qatar—muses in his journal: “Jim has so apotheosized his life as an epic of American courage and spirit that any criticism (or perceived criticism) is akin to sacrilege or even treason.”

As deputy assistant secretary for installations and facilities, and then as assistant secretary for manpower and reserve affairs, Untermeyer, now 69, worked intimately with Webb in the Navy Department, and kept a meticulous journal of his close encounters; Untermeyer was so faithful a diarist that Webb once ordered him during a particularly sensitive meeting (on the then-troublesome issue of women in the Navy): “Chase, stop taking notes.”

Untermeyer, who has been close to the Bush family for four decades, is enthusiastically supporting Jeb Bush for president, but told The Daily Beast on Monday he would be perfectly comfortable if Webb somehow beat the very long odds and ended up in the Oval Office.

But in his journal from 1987, he muses: “I suspect Webb has gotten nervous about championing the women’s issue probably because he is truly against women in the military and detests those who keep pushing the matter.”

At one point, Untermeyer writes in his journal (a habit he started at age 9): “Jim is an even moodier person than John Lehman, with a fiery temper of the sort that John suppressed. His work habits and accessibility may be just as chaotic as Lehman’s...I consider him [Webb] the preeminent member of my generation of Americans, and I am fortunate to know him.”

Despite his myriad accomplishments, Webb—who grew up a self-proclaimed “redneck” in a military family—was also oddly insecure about certain hot-button issues, such as whether an underling had attended an Ivy League college.

When one of his assistant secretaries returned to work from a three-week senior management course at Harvard’s Kennedy School of Government, Webb’s greeting was: “Are you an asshole yet?”

Untermeyer, a Harvard grad, was spared from such hazing only because he had served in the ROTC and then aboard a Navy ship during Vietnam.

In an anecdote worthy of a Peter Sellers comedy, Untermeyer recounts how Webb once decided to mingle with underlings in the Navy Department, poking his head into their cubby holes and engaging in friendly conversation, when he came upon a wall decoration in the office of Untermeyer’s executive assistant, a female Navy captain.

The decoration—which was actually on a bulletin board over the desk of the captain’s secretary—was a satirical cartoon titled, “The Evolution of Authority.”

It showed an ape’s footprint, then a man’s shoeprint, “then the distinctive imprint of a high-heeled shoe,” Untermeyer writes. “It was a feminist joke, and a mild one at that.”

A half-hour after Webb returned to his office, he phoned Untermeyer, seething with anger about the cartoon. “We should be applying the same standard we would to a male,” he barked. “That was inappropriate and unnecessarily inflammatory. If a man had put something like that against women on his wall we would be stuck with an EEOC complaint.”

In the ensuing couple of days, Untermeyer kept looking for an opportunity to sneak into the captain’s office and stealthily remove the cartoon, and Webb checked up on his progress. “Is it gone?” he asked.

At one point, Untermeyer succeeded, at night, when everybody had gone home, only to have a new copy of the cartoon restored the next day.

He was forced to remove it a second time, lest Webb wander by and have a full-on meltdown.

Untermeyer acknowledges that perhaps Webb or other personages who show up in his journal will be displeased with some of these stories.

“In defense, I reply that they did it; I only recorded it,” he writes in his book. “And, while it may be of only slight comfort to them, I have omitted a great deal that they might find even more disagreeable.”

This article was amended Tuesday, July 7 at 1:30 p.m. to include a comment from Jim Webb’s campaign spokesman.