At the very first Democratic debate in Las Vegas, each candidate was asked which enemy they were proudest of.

While others listed the coal lobby, Republicans, and special interests, former Virginia Sen. Jim Webb answered: “I’d have to say the enemy soldier that threw the grenade that wounded me. But he’s not around right now to talk to.”

A few scattered laughs from the pews. Webb smiled fondly.

For many Americans, that was the first and last time they heard from or thought about Jim Webb.

Until last week, when Webb lunged back in the news after telling MSNBC’s “Morning Joe” that he would not vote for Hillary Clinton — and had in fact flirted with the idea of voting for Republican front-runner Donald Trump.

Webb continued: “If you’re voting for Donald Trump, you may get something very good or very bad. If you’re voting for Hillary Clinton, you’re going to be getting the same thing.”

This is unthinkable for most Democrats. While there has been widespread and vocal opposition to Hillary Clinton’s semi-coronation as the Democratic nominee, supporting Donald Trump as a Democrat is just about as crazy as supporting him… as a Republican. What gives?

Webb presents himself as the voice of a supposedly forgotten corner of the Democratic Party: rural middle and working class white men.

The descendant of Scottish-Irish immigrants and a son of rural Appalachia, Webb has said that the Democratic establishment, “[has] kind of unwittingly used this group, white working males, as a whipping post for a lot of their policies.”

Webb’s also an active supporter of gun rights and wants to limit the scope of affirmative action, particularly for groups other than African Americans. As Anderson Cooper noted duing the first Democratic debate, in 2000 Webb said affirmative action “has within one generation brought about a permeating state-sponsored racism that is as odious as the Jim Crow laws it sought to countermand.”

Webb actually hasn’t even been a Democrat that long, having switched parties to challenge Republican Sen. George Allen in Virginia in 2006. He’s still some conservatives’ favorite Democrat.

Webb’s pleas to the Democratic Party find no greater support, strangely, than in Donald Trump’s success.

The former senator argues that the Democratic Party should devote itself to a program of economic uplift aimed at all Americans generally, and to poor and working-class whites specifically. Trump’s positions on immigration and trade stem from a stated commitment to improve the economic prospects of that group, ostensibly by deporting undocumented immigrants that are taking “American jobs,” and “winning” trade deals.

On his webpage, Trump states that by negotiating better trade agreements, “The results will be huge for American businesses and workers. Jobs and factories will stop moving offshore and instead stay here at home. The economy will boom.”

In 2014, Webb told an audience in Richmond, Virginia that the Democratic Party “has lost white working-class voters by becoming ‘a party of interest groups.’” Similarly, Trump has said that the GOP is “controlled by lobbyists…controlled by their donors, they’re controlled by special interests. … If you’re looking at making our country great again, they’re not going to do it.” The party establishments, to believe Webb and Trump’s pitches, aren’t representative of white voters.

Webb seems to sympathize with the disaffected white men at Trump rallies, and he’s not alone. Nate Cohn, writing about Trump supporters for the New York Times, observed that “a large number of traditionally Democratic voters have long supported Republicans in presidential elections. Even now, Democrats have more registered voters than Republicans do in states like West Virginia and Kentucky, which have been easily carried by Republicans in every presidential contest of this century.”

The Democratic Party has been losing white voters — particularly white male voters — by increasingly large margins in recent elections. According to exit polling from November 2014, Democratic candidates won only 34 percent of white men, and the 30-point difference amongst the parties in this demographic is at its largest in 20 years.

Trump’s message could very well appeal not only to Webb, but to a significant subsection of Democratic voters as well.

More than one in ten people in Virginia live below the poverty line. It’s also 70% percent white. Webb’s home state has typically been a swing state in presidential elections, and it wouldn’t be a surprise if the state went to Trump in November, should he be the party’s nominee.

Jim Webb might make sure of that himself.

Follow Benjamin Powers on Twitter @bnpowers8.

Photo: Former U.S. Senator Senator Jim Webb speaks during a news conference in Washington October 20, 2015. REUTERS/Yuri Gripas