If former Virginia Sen. Jim Webb runs for the Democratic presidential nomination in 2016, he'll do so as a man with very little to lose. And for Hillary Clinton, the party's undeclared frontrunner, that could potentially be a big problem.

When Webb retired from the Senate in 2013 after only one term, many assumed his decision to forego reelection marked his exit from the political stage. He was always an outsider, never cultivating deep ties with Democratic donors and party elders during his time in Washington. And at 69 years old, he's probably not eyeing a future in electoral politics beyond 2016.

"He's always been an unnatural political animal," Webb's Senate campaign manager Steve Jarding said with a laugh. "And I don't say that pejoratively."

Last November, though, Webb jumped back into the fray, surprising observers by becoming the first Democrat to take the step of forming a committee to explore a presidential bid in 2016. In his announcement video, he warned that America was at a "serious crossroads" and touted his own record of leadership.

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To say that Webb would begin the 2016 race as a longshot might be considered charitable, given Clinton's early dominance. But it's clear he can't be dismissed out of hand.

A former Marine and decorated war hero, Webb was an assistant secretary of defense and secretary of the U.S. Navy before becoming a senator. He has no shortage of gravitas.

He's also aggressively opposed recent foreign military incursions and championed efforts to rein in Wall Street - both positions that could endear him to the Democratic base, which is seeking a progressive alternative to the Clinton juggernaut.

Webb is not exactly the ideal champion of the left, though. He's staked out more conservative positions on gun control, affirmative action, immigration, and environmental issues that could be problematic if he hopes to become a progressive favorite.

It is, in all, an unusual but intriguing record. And it has some wondering whether Webb could emerge as a real player in 2016.

"He brings a certain level of prestige and gravitas to the debate, a kind of working class appeal," said Jarding.

"Webb certainly passes the 'threshold of credibility' standard...He could become a serious candidate," added Tad Devine, a veteran Democratic strategist who's advising Sen. Bernie Sanders, another potential 2016 candidate.

Veteran D.C. journalist Al Hunt put it most succinctly last year: "Jim Webb could be Hillary Clinton's worst nightmare."

The making of Jim Webb

Webb was born in Missouri in 1946 to a military family that relocated frequently during his youth. He graduated from high school in Nebraska and spent a year at the University of Southern California before finishing undergrad in 1968 at the U.S. Naval Academy.

After college, Webb was commissioned as a second lieutenant in the U.S. Marine Corps and sent to Vietnam. He distinguished himself in the war, earning a Navy Cross, two Purple hearts, the Silver Star and two Bronze Stars, and he was soon promoted to first lieutenant. Due to several injuries he sustained while fighting, Webb was granted a medical retirement shortly after he returned home.

He received his law degree from Georgetown University in 1975 and soon joined the staff of the House Committee on Veteran's Affairs. In 1984, Webb was appointed Assistant Secretary of Defense under then-President Ronald Reagan, and in 1987, Reagan appointed him Secretary of the Navy. He resigned from the post in 1988 due to a dispute over the size of the Navy and spent the next few years as a filmmaker and author.

In 2006, Webb ran as a Democrat against then-Sen. George Allen, R-Virginia. He campaigned as a strong opponent of the Bush administration's war in Iraq, famously wearing the combat boots of his son, who was fighting overseas, at all of his campaign events. Allen was heavily favored to win the race at the outset, but after he came under fire for directing the slur "macaca" at a South Asian man tracking one of his events , Webb surged to victory, pulling off the most surprising Senate victories in recent memory.

"Some people called it the upset of the century," recalled Jarding. "There was no way in hell Jim Webb was going to win that race, and everybody knew it, except Jim Webb."

As senator, Webb was remembered primarily for delivering a well-received Democratic response to Mr. Bush's 2007 State of the Union address, and for his efforts to pass a 21st century G.I. bill enabling more veterans to go to college and receive job training.

Much of Webb's political persona draws on his heritage as a Scotch-Irish American with roots in Appalachia and Middle America. He's counseled Democrats not to give up on attracting the white, working-class voters who have sided against them in recent elections, and he's calibrated his message to appeal to dispossessed Americans in both rural and urban areas.

That's led him to embrace a type of economic populism, supporting efforts to tackle income inequality and rein in Wall Street. But it's also allowed him to stake out more conservative positions on cultural issues like gun control and affirmative action.

Jim Webb on the issues

Gun Control

While much of his party has supported stricter restrictions on gun ownership in America, Webb has taken a different tack by emphasizing the importance of Second Amendment rights. As a senator, he voted to allow firearms in checked baggage on Amtrak trains, he supported a measure to prohibit the provision of foreign aid to any organization seeking to impose registration or tax requirements on U.S. gun owners, and he sponsored a proposal allowing veterans to register an unlicensed gun they acquire while abroad.

In 2007, after an aide in his Senate office was arrested for trying to bring a gun into the Capitol complex, Webb distanced himself from the episode but took the opportunity to offer a rousing defense of the right to bear arms. "I believe wherever you see places where people are allowed to carry, generally the violence goes down," he said.

Affirmative Action

Webb has also distinguished himself from the rest of his party by opposing race-based affirmative action programs in the college admissions process. He's argued that the programs once helped address the legacy of institutional racism, but that they now provide a misleading read on the face of poverty in America, disadvantaging poor, white kids from rural areas. In a 2010 Wall Street Journal op-ed, Webb called for a switch from race-based programs to need-based assistance programs that would help poor students of all races.

"Those who came to this country in recent decades from Asia, Latin America and Africa did not suffer discrimination from our government, and in fact have frequently been the beneficiaries of special government programs," he wrote. "The same cannot be said of many hard-working white Americans, including those whose roots in America go back more than 200 years."

In a speech last year at the National Press Club, Webb said the experience of white Americans in downtrodden rural areas undermines the "false premise that if you are white, you by definition have begun with some kind of socioeconomic advantage."

Economic Policy

In Webb's 2007 State of the Union response, he argued that America's economic health should be measured "not with the numbers that come out of Wall Street, but with the living conditions that exist on Main Street."

That kind of economic populism has lent itself to a number of proposals to crack down on the financial services industry and promote economic opportunity and mobility. As a senator, he supported a measure to tax any bonus given to an executive at any big bank or financial firm that received government assistance during the crisis of 2008. He also pushed for a hike in capital gains taxes in 2011, arguing it would help address the growing problem of income inequality.

Foreign Policy

Webb's earlier career in the military and his work at the Defense Department spoke to a generally hawkish take on the use of American military power - he's defended the reasoning behind the U.S. war in Vietnam, for example. But since he entered the political fray in 2006, he's been a strong opponent of U.S. military interventions.

He was a vocal critic of the second Iraq war, dubbing President Bush's decision to invade in 2002 America's worst strategic blunder in recent memory. He opposed President Obama's decision to use U.S. military force to help oust Libyan dictator Moammar Qaddafi in 2011, and he's spoken out against those who advocate arming Syrian rebels to fight Islamic extremists and government thugs in that country.

"There is no such thing as the right of any President to unilaterally decide to use force in combat operations based on such vague concepts as "humanitarian intervention," Webb said in his speech at the National Press Club. "If a treaty does not obligate us, if American forces are not under attack or under threat of imminent attack, if no Americans are at risk, the president should come to the congress before he or she sends troops into harm's way."

Why he might be a viable Clinton alternative - and why not

Of the non-Clinton Democrats eyeing a bid in 2016, some believe Webb may be the most willing to attack the party's ostensible frontrunner.

Vice President Joe Biden is seen as too collegial with Clinton to attack her directly, and the same is true of Vermont Sen. Bernie Sanders. Massachusetts Sen. Elizabeth Warren is beloved by progressives, but she's repeatedly said she won't run in 2016. Former Maryland Gov. Martin O'Malley is making early moves to position himself as the progressive alternative to Clinton, but there are questions about how aggressive he's willing to be - would he attack his party's likely nominee if he knew it meant sacrificing a political future beyond 2016?

That leaves Webb, a man who's rarely shied away from a political fight he deems worthwhile.

"I think he's used to the rough and tumble of politics, and I think that he's very different from Biden or Sanders, for example," Devine explained. "Part of Webb's whole appeal is going to be that he's a tough guy....I could see Webb being a tough guy on Hillary to try to prove that he'd be a tough guy on [possible 2016 GOP nominee Jeb] Bush later on."

Webb's progressive positions on economic issues and his outspoken opposition to foreign entanglements could resonate with Democratic primary voters, especially given Clinton's own close ties to Wall Street and her relatively hawkish profile on defense issues.

"The anti-war folks will love Jim, the anti-Wall Street folks will love Jim," said Jarding.

Larry Sabato, a political science professor at the University of Virginia, said Webb "could use both issues to some effect should he run."

"A sizable minority of Democrats has not yet cast its lot with Clinton, and some will vote for a credible opponent in the primaries and caucuses," Sabato said. "Jim Webb has a distinguished record, including a Senate term, so he qualifies."

The problem, though, is that Webb's stated beliefs don't always place him to Clinton's left: he's more of ideological hodge-podge than a progressive champion. To court the left, he'd need to explain some conservative positions on cultural issues, along with some of his earlier hawkish views on foreign policy.

"If you're going to challenge Clinton, you have to do it from the left, not the center," said Devine. "Webb certainly has a lot of populist appeal, but if you look at his record, going back to service in the Reagan administration, he's got a lot of positions on issues...and things he's said in the past that will position him to Clinton's right."

"When you get Jim Webb, you get Jim Webb. You get the polish, you get the warts, but this is not a guy who's going to take the easy path to electoral politics," Jarding said. "I don't think he's going to necessarily going to compromise at levels that a lot of folks would like him to compromise."

On a more mechanical level, it's not clear Webb (or any Democrat) will be able to raise the funds needed to mount a serious bid, given Clinton's forbidding early dominance.

"The biggest and toughest benchmark for him is going to be -- can he put together the resources to run a national campaign?" Devine said. "I don't think there's any doubt that he has credibility in terms of his substance."

"He wasn't the best campaigner, he detested fundraising," admitted Jarding. " A lot of candidates find campaigning very taxing, they hate to raise money, and they just won't admit it. But he did."

As he considers his strategy going forward, Webb has been decidedly coy about criticizing Clinton thus far. He told a radio interviewer during a visit to Iowa last August, for example, that it would "take up the whole show" for him to critique Clinton's record as secretary of state.

"I think there's time to have that discussion later," he added, winking at the likelihood of fireworks to come.