Barack Obama’s Vice Presidential vetting team - what’s left of it - will come across compelling, perplexing and troublesome issues as it scours every last detail of the backgrounds of the Senator’s possible running mates.

Below is the first in a series in which Donkey Dish staff writers make their case for several Vice Presidential candidates we believe deserve consideration.

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Out of nowhere and into the forefront of many Democrats’ minds as a strong contender among many V.P. options for Sen. Barack Obama is Virginia Sen. Jim Webb, a decorated Vietnam veteran and former U.S. Navy Secretary.

Jim Webb is a former military leader who opposed the Iraq war from the start - a competent person for the job, first and foremost - and he just happens to be a former Republican hailing from the suddenly competitive state of Virginia.

But perhaps most intriguingly, he is in many respects the poster candidate of the 21st century Democratic Party, representing an emerging style and philosophy that have expanded the political map already since 2004.

Sen. Jim Webb introduces Sen. Barack Obama at a campaign rally.

The Democrats’ themes of change and populism have resonated on the campaign trail this year - as evidenced by the party’s chosen nominee.

Their only weak point - at least as far as many perceive it - is national security.

The military still doesn’t trust Democrats, even as the incompetent use of the troops in Iraq by the Bush-McCain camps have caused disgust.

Could Jim Webb be the Democrat who wins the military back?

Webb has already proposed a G.I. bill that some Republicans, including John McCain, have opposed — because they believe it’s too generous.

This is a key talking point that has yet to be given much media attention, and when it does, who better to lead the charge than Jim Webb?

Best of all, on top of his ability to effectively neutralize the GOP on military and defense issues, Webb is far from a one-trick political pony.

In his new book, A Time to Fight, he advocates core Democratic principles such as the assurance of social and economic equity, melded carefully with enlightened, pragmatic, and ideologically centrist world views.

It’s a difficult balancing act, one made more worse by Jim Webb’s love for the Confederacy (seriously, read his books) and his gaffe-prone (some would say redneck) nature. He’s guaranteed to produce some bad sound bites.

But given the political climate in 2008, and the man running atop the Democratic ticket, a Barack Obama-Jim Webb ticket is so crazy it just might work.