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By all accounts, he is an extreme long shot, but Jim Webb has set up an “exploratory committee” to see about running for president in 2016.

The former senator from Virginia, writer (of, among other books, the 2014 memoir “I Heard My Country Calling” and a critically acclaimed war novel, “Fields of Fire”) and veteran of Ronald Reagan’s administration said in his announcement (the first of what will no doubt be many by both Republicans and Democrats): “Is it possible that our next President could actually lay out a vision for the country, and create an environment where leaders from both parties and from all philosophies would feel compelled to work together for the good of the country, despite all of the money and political pressure that now demands they disagree? I believe it is possible.”

But most political pundits and prognosticators point out the obvious: Mr. Webb, with scarce resources at the moment, would face a steep climb to the Democratic nomination against the overwhelming favorite, Hillary Rodham Clinton (assuming she runs). Even Steve Jarding, who worked on Mr. Webb’s 2006 Senate campaign, told David Freedlander at the Daily Beast that “at this point, you wouldn’t bet on him.”

Mr. Webb’s announcement video — or at least its style — may not inspire legions of new followers, as Mr. Freedlander points out: It “had all the slick production of the instructional video shown before jury duty.”

Yet the style might actually be a deliberate “anti-style” that will find a better reception with voters who these days don’t have much taste for conventional Washington politicians — for them, Mr. Jarding suggests, Mr. Webb might be their stand-in.

Noah Millman at The American Conservative agrees: “He’s a genuinely independent person, the exact opposite of the careerist climber. We desperately need more people like him in our politics.”

Mr. Webb could bring a robust populist message, Mr. Freedlander argues, adding that he talks “about not just curbing the power of big banks but about an inequality agenda that goes beyond raising taxes and the minimum wage in order to help lower middle-class families gain more of a foothold.”

This is one reason Al Hunt, writing at Bloomberg View, says, “Jim Webb could be Hillary Clinton’s worst nightmare.”

Mr. Hunt says that Mr. Webb “has long taken a populist, anti-Wall Street stance” and, noting his well-received 2007 response to President George W. Bush’s State of the Union address, says that Mr. Webb “declared that the health of American society should be measured ‘not with the numbers that come out of Wall Street, but with the living conditions that exist on Main Street.’”

“He pushed a measure to slap a special tax on big bonuses paid out by Wall Street companies that received government assistance during the financial crisis,” Mr. Hunt adds.

Above all, observers also emphasize his foreign policy vision. William Greider at The Nation says, “Given his résumé and valor in war, Webb has the authority (and the guts) to provoke a profound national debate about the nature of U.S. militarism.”

He was against the war in Iraq and, as David Weigel reports at Bloomberg Politics, he’s been making the claim that America has “‘fallen into that Pandora’s box of the killer of empires’ by over-committing and occupying in the Middle East and Arab world.”

Mr. Hunt summarizes this view: “What he does possess is a long-held and forceful opposition to U.S. interventions in Iraq and Libya, and potentially Syria.”

P.M. Carpenter, writing at his blog, sees any comparison with Hillary in this area as advantageous to Mr. Webb: “Webb has been consistently right about America’s recent wars, and Hillary has been consistently wrong. His theorems: ‘An important caveat on how our country should fight the terrorists if they are a direct threat to our national security is: do not occupy foreign territory,’ and ‘Never get involved in a five-sided argument.’”

Mr. Webb tells Ryan Lizza at The New Yorker, “I’ve said for a very long time, since I was Secretary of the Navy, we do not belong as an occupying power in that part of the world,” and adds, “This incredible strategic blunder of invading caused the problems, because it allowed the breakup of Iraq along sectarian lines at the same time that Iran was empowering itself in the region.”

In sizing up Mr. Webb’s chances, then, on paper, most observers suggest that if his appeal succeeds anywhere, it would be standing on ground to Hillary’s left. Yet Harry Enten, a writer and political analyst at 538, makes a case for a “his moderate credentials” as the path to follow. He notes that Hillary does best with Democratic voters who consider themselves liberal, “but there’s more room on her right than her left” and “anti-Clinton voters prefer a more conservative option.”

Josh Kraushaar at National Journal, in estimating Mr. Webb’s candidacy, suggests that it’s less about where he stands in the party’s spectrum and more about how the party has changed in what it stands for: “That he’s treated more like a fringe figure these days is a testament to how far his party has drifted from its roots,” he writes. “The base of the Democratic Party now finds itself united by cultural issues, not economic ones — and Webb is badly out of step with the changed sentiment.”

Indeed, the most common view of Mr. Webb’s candidacy is a pessimistic one.

Skeptics point to questions about his temperament and taste for retail politics. Rob Garver at The Fiscal Times writes that he “has never been the most enthusiastic of politicians,” and after a distinguished career in the armed forces, “carried that no nonsense military attitude with him into the political arena, which is more typically full of nonsense.”

Aaron Blake, writing for The Fix at The Washington Post, lays out several criticisms against Mr. Webb. “He retired after one term in the Senate and didn’t seem to particularly enjoy being in public life.” He also refers readers to Larry Sabato, a University of Virginia professor commonly referred to as the “dean” of Virginia politics, who said after Mr. Webb’s retirement from the Senate: “He has been an excellent United States senator, but he is a terrible politician. He doesn’t suffer fools gladly, he doesn’t enjoy glad-handing.”

Furthermore, Mr. Blake finds Mr. Webb “very dour,” and adds: “He has negative charisma. The Fix believes that presidential races have a charisma threshold, by which we mean that candidates need to be at least somewhat compelling to a national audience to achieve viability.”

He might also bring cultural baggage, including, as Mr. Blake points out, what some see as him “being insensitive to women.” As an example, he and others point to a 1979 article in The Washingtonian magazine called “Women Can’t Fight,” which argued against women in combat (Mr. Webb apologized for the article in 2006, calling it an “overreach”).

Mr. Blake also notes that “Webb has spoken fondly of his Confederate roots and defended the Southern states’ decision to secede, even citing the ‘Nazification of the Confederacy.’”

Citing Mr. Webb’s call for a greater spirit of cooperation in Washington in his announcement comments, Ed Kilgore at the Washington Monthly blog Political Animal writes: “I really, really don’t think the average potential primary supporter of Webb against Clinton is going to kick out the jams for a candidate who thinks the real problem in Washington is insufficient bipartisanship. Been there, done that, with Obama.”

Mr. Millman, though taken with the idea of Mr. Webb’s candidacy, nonetheless sees its potential shortcomings: “Inasmuch as some Democrats’ big worry about Clinton is that she’s not a particularly good politician, Webb is hardly an attractive alternative. Plus, the current Democratic President is a standoffish writerly personality. Do the Democrats really want to nominate another one?”

Mr. Webb is aware of his status. As Mr. Lizza reports, “I noticed a picture of Don Quixote on Webb’s wall of military treasures. He laughed when I asked about it. ‘The beauty of Don Quixote is not that he dreamed impossible dreams,’ he said. ‘It’s that, because he believed, he caused other people to believe.’”

And given the vicissitudes of primary battles — 2008 is a relevant example — as Mr. Lizza writes, there is still a glimmer of hope: “In every fight for the Democratic Presidential nomination in the past five decades, there has come a moment when the front-runner faltered. ‘Nature abhors a vacuum, and so does politics,’ Anita Dunn, a Democratic strategist, told me. Voters in the early states, perhaps spurred by a sense of civic responsibility, begin to take an interest in candidates they had previously never heard of. Those candidates seize on issues, usually ones that excite the left, that the front-runner, focussed on the general election, has been too timid to champion.”