Former senator Jim Webb (D-Va.), pictured in 2012, he said he is “seriously looking at” running for president in 2016. (Tom Williams/CQ Roll Call)

Jim Webb has built an entire persona on being a contrarian outsider whom no one sees coming. The Democratic former senator from Virginia has regularly unnerved members of his party by citing a GOP icon, Ronald Reagan, as his hero. His storied unwillingness to play by the accepted rules of modern-day campaigns has established him as one of the true political eccentrics of the age.

Which explains why most experts severely discount Webb’s chances of ever becoming president — and why Webb is genuinely thinking about a White House bid in 2016.

“I’m seriously looking at the possibility of running for president,” he said in a speech last week. “But we want to see if there’s a support base from people who would support the programs that we’re interested in pursuing.”

Such a base in the Democratic Party could be hard to find in light of Hillary Rodham Clinton’s popularity and dominant standing among Democrats. Any potential challenger to Clinton’s expected bid for the party’s nomination would have to be regarded as a long shot, and maybe none more so than Webb, a one-term senator who once served as secretary of the Navy in Reagan’s administration.

A Washington Post-ABC News poll in June showed Webb with only 2 percent support among Democrats nationally, which put him 64 percentage points behind Clinton in that survey. Add to that his political baggage, especially on women’s issues, and his chances seem even slimmer.

Hillary Rodham Clinton might not be the only candidate on the left who launches a presidential campaign. Meet the guys who may try to take her on: former senator Jim Webb (Va.), Maryland Gov. Martin O’Malley, Vice President Biden and Sen. Bernie Sanders (I-Vt.). (Jackie Kucinich/The Washington Post)

Still, as the national debate turns increasingly toward questions of U.S. military involvement abroad, Webb — a Vietnam veteran who has carved out a profile as an antiwar warrior — may be uniquely positioned as a disruptive force on issues where many Democrats consider Clinton compromised.

“Remember, one of the reasons Obama did so well in Iowa was because he said he would end the wars,” said Marcos Rubinstein, who directed antiwar Democrat Dennis Kucinich’s 2008 presidential campaign in Iowa. “That is why he was able to beat Clinton, and Iowa remains full of Democrats who are looking for a peaceful message.”

In a race against Clinton, the party’s ultimate insider, Webb, 68, would be an acerbic iconoclast who would avoid the ways of modern presidential politics. As a lawmaker, he refused to raise money in the traditional fashion, and he declined the social invitations and cable-news bookings that have come to define the daily routine for many of his former colleagues.

In his speech last week at the National Press Club, Webb spoke to what he believes is a sense of economic dread and war weariness in the electorate.

“It’s rare when the economy crashes at the same time we are at war,” he said. “The centrifugal forces of social cohesion are spinning so out of control that the people at the very top exist in a distant outer orbit, completely separated in their homes, schools and associations from those of us who are even in the middle.”

But even Webb’s biggest boosters know he faces extreme odds.

“It would be an uphill fight, almost like climbing a wall,” former senator Bob Kerrey (D-Neb.) said in an interview. “He would be running against someone who simultaneously has two television shows based on her. She is a political figure with such remarkable strength ahead of the campaign, unlike anything I’ve seen in my lifetime. The question is whether all the minds of those who would vote at the convention are closed.”

Kerrey, who in 1992 contended for the Democratic nomination that Bill Clinton eventually won, has been urging Webb to challenge Hillary Clinton in 2016. Over phone calls in recent weeks, the two friends — Kerrey is also a decorated Vietnam veteran — have concluded that Clinton could be vulnerable. They believe Webb could win over activists in early primary states who are uncomfortable with Clinton’s vote as a senator in 2002 to authorize war in Iraq and her support for the strategy President Obama is pursuing to fight the Islamic State.

A contrarian voice

Webb “would speak forcefully and have tremendous credibility on the issue of war and peace,” Kerrey said. And with war raging, some Democrats may seek a dissenting spokesman to counter the hawkish impulses that have shaped Clinton’s worldview.

Webb’s comments last week about his 2016 intentions came as he delivered a stinging rebuke of Obama’s foreign policy.

He said in an interview that his return to public life is driven partly by a desire to pull his party away from its current posture and to revive some skepticism about U.S. military action in the Middle East.

“If you go back and look at the remarks I was making from the time this administration got involved in the Arab Spring, I said it was an unprecedented use of presidential power — no treaties, no Americans attacked, no imminent threat of attack, no Americans to be rescued,” Webb said. “Secretary Clinton and I have worked well together, but the Arab Spring is a different question. . . . This administration, collectively, made some very bad decisions, and they now have to climb out of a deep hole.”

Clinton and other senior Democrats have mostly backed the president’s efforts. Clinton was an early proponent of intervention, even before Obama came around.

The specter of a Clinton candidacy loomed over the proceedings at the National Press Club, but Webb resisted criticizing her by name. Instead, he cited disagreements he had with the Obama administration during Clinton’s tenure at the State Department.

“I’m not here to undermine her,” Webb said during a question-and-answer session. “I’m here to explain where my concerns are.”

When pressed on whether his comments were meant as a direct critique of Clinton, Webb assumed a wry smile: “As you know, I’m a writer and I choose my words carefully. . . . This isn’t personal.”

Oddly, if he ran, the former Reagan official would probably be challenging Clinton from the left, but he could expect sharp disagreements with the Democratic base on numerous issues. He is, for example, an advocate of gun owners’ rights, and last week he praised both Reagan and Franklin D. Roosevelt for their leadership abilities.

“Some of my Democratic friends don’t like it when I say that,” Webb said. “But Ronald Reagan was once a Democrat and still a leader. He brought strong people around him, and he had a vision for where he wanted to take the country.”

If he did enter the race, Webb would run as a Democrat rather than as an independent.

“I’m a Democrat, and I have strong reasons for being a Democrat,” he said, citing the party’s alliance with the poor and its message of “economic fairness” as integral to his own politics.

Visits to early-voting states

Webb said in the interview that the brewing populism in Democratic ranks, particularly at the grass-roots level, resonates with him. That same shifting tide in the party has led some Democrats’ efforts to draft Sen. Elizabeth Warren (Mass.), a progressive favorite, to run against Clinton.

Steve Jarding, a former political consultant for Webb, said Webb could run a “maverick campaign” comparable to the presidential bids of Republican John McCain in 2000 and Kerrey in 1992.

“In this climate, there is a thirst in the electorate for someone who can shoot straight, and Jim knows that,” Jarding said. “I don’t think he’s intimidated by the long odds. It’s not in his makeup to be fearful, and I think he’s putting a trial balloon out there because he is probably going to run.”

Several influential Democrats in early primary states said Webb could eventually gain traction should the left wing of the party sour even more on the airstrikes in Syria and desire an aggressive, antiwar populist to be the Democratic standard-bearer.

“I don’t know enough about him, but there is always room for more in a presidential race,” said Iowan Jan Bauer, chair of the Story County Democratic Party.

Bret Nilles, another Iowan and chairman of the Linn County Democratic Party, said he met Webb in August in Cedar Rapids. “He’s not quite as dynamic as other Democrats,” Nilles said. “If he comes here again, he’s going to have to get an organization together.”

In October, Webb will head to New Hampshire, where he will speak at St. Anselm College, near Manchester, and stump for Sen. Jeanne Shaheen (D).

A Webb campaign would start with little national name recognition, little money and questions about his appeal. For a party that has made improving the lives of women a central part of its pitch this year, Webb has a controversial history of statements. Webb, who has Confederate roots, has praised Rebel troops for their “gallantry” during the Civil War, and in 1979 he wrote a Washingtonian magazine article questioning whether women should be on the front lines of battle.

Robert Shrum, a longtime strategist for Democratic presidential candidates, said Webb is “intriguing” as a political figure but would enter a race stacked against him. “I think Hillary Clinton is going to be the nominee, and I don’t think she would run in any of the caricatured ways it’s assumed she would run,” he said, adding that “there is not a lot of room to take her on,” be it as a Democratic dove or otherwise.

In June, Webb began to solicit donations for Born Fighting, his mostly dormant political action committee, and wrote a letter to supporters about his desire to jump back into national politics.

“When I left the Senate in January, 2013, I decided to take a full year away from all media interviews, editorial articles, and direct political activities,” he wrote. “I am now ready to re­enter the debate, and I am asking that you consider helping me do so.”

In July, Webb gathered former aides and supporters for a reunion in Falls Church, Va. Soon after, working with his adviser Jessica Vanden Berg, an Iowa native, he began to map out a travel itinerary.

“I had a great time in Iowa,” Webb said of his trip there last month. “I really did. We drove about 800 miles and did 15 events.”

He would have to go much further to mount a real challenge to Clinton.

“Secretary Clinton is the dominant figure,” said former senator Evan Bayh (D-Ind.), a friend of Webb’s and a Clinton supporter. “But I don’t anticipate her being unopposed.”