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Jim Webb tests the limits of a maverick's appeal

Jim Webb is a proudly unorthodox figure, but does he have what it takes to build a team?

Seven months after forming a presidential exploratory committee, former Sen. Jim Webb officially jumped into the 2016 presidential race Thursday. The surprise 2,000 word announcement email, coming as many headed out of town for the July 4 holiday weekend, was a typically unorthodox move for Webb.

The former senator, author, decorated Marine combat veteran and Navy secretary is a true maverick. He’s a rebel who refuses to play by Washington’s rules, and he has excited some liberals with his anti-conformist ethos.

RELATED: Jim Webb announces 2016 bid for president

Webb’s refusal to play by the rules, and his willingness to break with convention, is considered refreshing in an age of deep dissatisfaction with politics. But it also means he often ends up alone, as when he defended the Confederate flag after the shooting massacre last month at a historically black church in Charleston, South Carolina.

By throwing out the political playbook and letting seven months pass by without building a real campaign infrastructure, Webb went from being the first potential candidate to declare an exploratory committee to being the 15th candidate to officially enter the race.

And his ideological heterodoxy and refusal to comport to anybody’s doctrine makes it unclear where he stands in a Democratic field that has so far broken down cleanly along ideological lines.

“He is not a natural ideological leader for any group in the Democratic Party,” said Steve Jarding, a Harvard professor who co-directed Webb's 2006 Senate campaign. “Jim's going to have a real difficult time introducing himself to the national Democratic electorate because of things like the Confederate flag.”

In his long-winded announcement message, Webb made no mention of key issues to many Democrats, like climate change, racism, women’s rights, LGBT rights and abortion. He recently won a presidential straw poll at a conference of conservative activists in Colorado. On Tuesday, he said he was “very proud of having worked in the Reagan administration.”

While his party has tacked to the left, Webb has remained as heterodox as ever. He supports the Keystone XL pipeline, has taken issue with affirmative action, and on Tuesday, he expressed concerns with President Obama’s executive actions on immigration.

Yet, Webb is to the left of Clinton and Obama on foreign policy, and one of the foremost champions of criminal justice reform in either party and the author of the post 9/11 G.I. bill. In his announcement message, Webb focused on his opposition to the Iraq War and the 2011 intervention in Libya – both clear shots at Democratic front-runner Hillary Clinton – and a populist economic message about reclaiming the American dream from elites.

Those messages are popular among liberals dissatisfied with Clinton, but will they be willing to accept Webb’s less doctrinaire stances as well?

Webb's plans often remain a mystery even to those closest to him. “Jim always plays things close to the vest,” said David “Mudcat” Saunders, the longtime Webb strategist who is helping out the presidential campaign on a volunteer basis.

RELATED: Jim Webb stands alone on the Confederate flag

“The day that he said he was not going to run again in the Senate, I found out that day. And the day he said he was going to do the exploratory committee, I found out that day,” Saunders said last week before Webb announced.

Webb’s staff thought the senator might announce his presidential campaign last Friday at a speech in Iowa, and they didn’t know his plans as recently as Tuesday.

“I wake up every morning thinking he will roll into a coffee shop and announce something to the wait staff,” Craig Crawford, Webb’s communications director, joked last week.

The isolation that comes with nonconformity was on display near Webb’s hometown last Friday night, 1,000 miles away from where the former senator was giving his speech in Iowa.

At a pep rally-like fundraiser in Webb’s backyard of northern Virginia, state Democrats were having a party without him.

Rep. Gerry Connolly declared northern Virginia to be “Clinton territory,” while Webb’s former Senate colleagues Mark Warner and Tim Kaine called Clinton “our choice for the future” and “our next president,” respectively.

Webb understandably dislikes the nitty gritty of politics, but his objections have alienated him from some Virginia Democrats, several operatives said. “He was more interested in Myanmar than he was in Martinsville,” said one longtime Virginia Democratic strategist, who said officials like county party chairs gave up on asking the former senator to do fundraisers for them.

The enthusiasm for Webb’s candidness may have reached a limit last month when he called for “respect” for the Confederate flag as an emblem of common soldiers who fought on both sides of the Civil War.

The reaction to Webb’s comments from Democrats in Washington and New York was swift and brutal. “I think he went from a parody to a complete joke,” said Ari Rabin Havt, a former staffer for Sen. Harry Reid staffer who now hosts a progressive show on Sirrius/XM radio.

Hank Sheinkopf, a New York-based Democratic strategist, said the comments single-handedly killed whatever slim shot Webb had at the nomination. “In the real world, he should save his money and buy a house, because he ain’t going anyplace in the Democratic Party,” he said.

The damage appears especially severe among black voters, a key Democratic voting bloc with whom Webb has never been a favorite. “It makes him a non-starter,” said Stefanie Brown James, who led outreach to black voters for President Obama’s 2012 reelection campaign. “It's a horrible way to start out for him.”

Webb is a writer used to exploring nuance, but the fine shading of his position on the Confederate flag was lost on most observers.

Several Webb allies say privately they would have preferred he stay away from the topic of the flag entirely. But Webb is not one to shy away from controversy if he believes in something.

The incident also underscored the racial gambit of his campaign. While Democrats in the post-Obama era have focused on getting minorities to the polls, Webb has said he wants to bring disaffected whites back into the fold.

RELATED: ‘The Dukes of Hazzard’ no longer immune to Confederate flag fallout

Ruy Teixeira, a Century Foundation demographer who studies the changing makeup of the electorate, has his doubts about that tactic.

“He seems to have this idea that he represents the forgotten majority of the Democratic Party, but it’s just not true,” said Teixeira. “The primary electorate is pretty heavily skewed towards college educated whites and minorities. So the idea that the would be a good candidate for that just doesn’t make a lot of sense.”

While Webb shares a strong independent streak and an aurora of populist authenticity with Sen. Bernie Sanders, the two presidential candidates could not be more dislike, and not just on policy.

Sanders is the product of a movement, and he is deeply embedded in it. Webb is lone-wolf individual, whose peripatetic career has followed his ambitions.

Some Democrats openly scratch their heads about why Webb is even running. “I just don't get what he's doing,” said Mo Elleithee, a former Clinton aide and top official at the Democratic National Committee, who now runs the Institute of Politics at Georgetown University.

We will likely learn much more in coming days and weeks as Webb rolls out his presidential campaign, now that he’s officially in the race. Few voters are paying attention at this early stage, and Webb's position on the Confederate flag may fade into the background.

Webb has surprised the political world before, as he likes to remind audiences, and maybe he can do it again.