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Tonight's Democratic debate is filled with people who are barely Democrats

Democratic field with border

Perhaps the oddest feature of tonight's first Democratic presidential debate is that most of the candidates participating are barely even Democrats.

One, Lincoln Chafee, is a former Republican senator who just became a Democrat in 2013. Another, Bernie Sanders, is a longtime independent who calls himself a "democratic socialist." And a third, Jim Webb, served as Ronald Reagan's secretary of the Navy, only becoming a Democratic politician during George W. Bush's presidency.

It's no coincidence that the small Democratic field is filled with people with such weak ties to the party establishment — it's a direct consequence of Hillary Clinton's assumed strength as a candidate. With the sole exception of Martin O'Malley, ambitious Democratic politicians who spent their whole careers in the Democratic Party chose not to challenge Clinton.

And make no mistake, those ambitious Democrats do exist. As Jonathan Bernstein wrote at Bloomberg View, there's a long list of plausible Democratic contenders — politicians with experience comparable to or more extensive than that of Marco Rubio, Rand Paul, Ted Cruz, or Scott Walker. In the Senate, for instance, there's Elizabeth Warren, of course, but there's also Colorado's Michael Bennet, Virginia's Tim Kaine (or Virginia's Mark Warner!), Ohio's Sherrod Brown, Minnesota's Amy Klobuchar, and New York's Kirsten Gillibrand. Among current or recent governors, Democrats have New York's Andrew Cuomo, Massachusetts's Deval Patrick, and Colorado's John Hickenlooper, among others.

So far, Clinton's campaign has proven weaker than many expected. But there's a reason practically no longtime Democrats are in the race to challenge her: They have built their careers and networks in the Democratic Party, and they calculated that the vast majority of their donors and supporters were likely to back Clinton. (Vice President Joe Biden is currently mulling a late entrance to the race — but the reason it's such a tough call for him is because of Clinton's overwhelming establishment support.)

The absence of more traditional Democratic candidates has opened the field to a group of iconoclasts — people who owe the party establishment little or nothing, and are unafraid to go their own way. As a result, Clinton's challengers are highly unlikely to win, but are perhaps more likely to make her uncomfortable on the debate stage by pressing her with ideas and arguments she'd rather not discuss.

For that reason, the Democratic debate could prove a lot more interesting than most expect, in part because it won't be limited to die-hard Democrats.

1) Bernie Sanders, independent and "democratic socialist"

Bernie Sanders
(Brendan Smialowski/AFP/Getty)

Bernie Sanders is definitely not the type to go along meekly with the party establishment's wishes. When Sanders first entered Vermont politics in the early 1970s, he didn't join either of the two major parties. Instead, he joined the antiwar Liberty Union Party, and became its long-shot candidate, losing campaigns for Senate and governor.

Eventually, Sanders decided to challenge the entrenched, five-term Democratic mayor of Burlington as an independent, and won. He described the local Democrats as his "most bitter enemies." In 1990, he became the first independent elected to the US House of Representatives in 40 years. He chose to caucus with the Democratic Party, and has been harshly critical of the GOP, but has kept his independent status since.

Sanders's entire political career has been focused on checking the power of the wealthy and corporations, and that's the theme of his current campaign too. He wants the Democratic Party to wage a rhetorical war on the billionaire class, to better mobilize the general public against them and break their power.

And that's what makes Sanders's campaign interesting: He's running not just as a critic of money in politics but as a critic of a Democratic Party — exemplified by Clinton — that he thinks has become too corrupted by big donors.

2) Lincoln Chafee, former Republican and independent

Lincoln Chafee
(Alex Wong/Getty)

Second, there's Lincoln Chafee, who was born into the GOP — his father was a famous Rhode Island Republican politician. Chafee, too, started his career in the Republican Party, serving as mayor of Warwick and then being appointed to take his late father's place in the Senate.

But the national GOP was moving further to the right, and Chafee refused to go along. As a senator, he repeatedly clashed with the Bush White House, voting against Bush's two big tax cut packages, the Iraq War, and the confirmation of Justice Samuel Alito. The conservative publication Human Events dubbed him the No. 1 RINO (Republican in name only) in the country. After losing reelection (to a Democrat), Chafee became an independent in 2007, and won Rhode Island's governorship three years later.

In May 2013, with his popularity hurt by Rhode Island's bad economy, Chafee tried to revive his political fortunes by officially becoming a Democrat. But with two strong Democrats already running in the party's primary, it soon became clear that Chafee would lose — and badly. So in September 2013, he announced he wouldn't run for reelection, saying he'd rather focus on governing.

Now, with his political career seemingly over and owing nothing to the Democratic Party establishment, he's running for president. In his campaign, he stressed the importance of good judgment and emphasized that he had voted against authorizing the Iraq War in 2002 — in contrast to Clinton. (Chafee was the only Senate Republican to do so.) He said he learned early not to trust the Bush administration and "the so-called neocons."

3) Jim Webb: Republican until the Iraq War

Jim Webb
(Chip Somodevilla/Getty)

Then there's former Virginia Sen. Jim Webb. Webb was born into a Democratic family, but he actually quit the party back during Jimmy Carter's presidency due to outrage over Carter's pardons of draft dodgers, as Elizabeth Drew recounts.

This led Webb to back Ronald Reagan's presidential candidacy in 1980, and when Reagan won, Webb joined his administration, eventually rising to become secretary of the Navy. This isn't some youthful flirtation Webb has since recanted. "I know all my Democratic friends get mad when I say that I think Reagan was a leader," Webb told Vox. "He ran, particularly in the first term, probably the best administration in my lifetime." Note the implicit critique there of the Clinton and Obama administrations.

Republicans twice tried to woo Webb to run for Senate after his service in the Reagan administration, but he demurred, though he did support George W. Bush in 2000.

As with Chafee, it was outrage against the Bush administration that drove Webb out of the GOP. Specifically, Webb strongly opposed the Iraq War, which he argued was an "attempt to export our ideology at the point of a gun." So in 2006, Webb announced he'd run for the Democratic nomination to challenge Republican Sen. George Allen. Webb won, and the six years he spent in elected office as a Democrat tops both Chafee's year and a half and Sanders's zero years.

But his instinctual willingness to defy the party line is clear. Webb is willing to challenge Clinton on the power of the wealthy, and on her hawkish foreign policy views. He's also emphasized his longtime support for criminal justice reform, which he fought hard for in the Senate, even though he says his advisers warned him it would be "political suicide," as he said in May. "Secretary Clinton yesterday gave a speech on criminal justice reform — I've been talking about this for nine years," he continued.

The exception: Martin O'Malley, Democrat for life

Paul J. Richards / AFP / Getty

So far, Clinton has managed to deter every ambitious longtime Democrat from running for president — except for Martin O'Malley.

O'Malley owes a great deal to the Democratic Party — indeed, he wouldn't even exist without it. That's because his very political parents met when they worked together on a newsletter for a Young Democrats group. His involvement in politics never really let up afterward — on his second birthday, his parents frosted a cake with the words "Martin for President 2004."

Right after he graduated after college, O'Malley worked for Gary Hart's presidential campaign, and for Barbara Mikulski's first Senate bid shortly afterward. During that campaign he met Katie Curran, the woman who would become his wife — she was working for her father, the Democratic candidate to became Maryland's attorney general.

Afterward, he went from the Baltimore City Council to the mayoralty to the Maryland governor's mansion. And now he has the unusual distinction of being the only Democratic primary challenger to Clinton who is unmistakably a Democrat.