It’s interesting to watch the highly variable reaction of political observers to the prospect of uber-lobbyist Ed Gillespie running against Mark Warner in Virginia this year. To Washington Establishment types like WaPo’s Mark Thiessen and Jennifer Rubin, he’s the cat’s meow, a skillful operative who can raise huge sums of money and make the election “about” Warner and his vote for Obamacare Obamacare Obamacare.

Politico‘s James Hohman is a lot more skeptical:

Gillespie, 52, will enter the race as the heavy underdog. Aside from his time as a top D.C. lobbyist, he’ll have to fend off attacks from his right on issues from immigration to deficits to the Wall Street bailout — without damaging his prospects against a popular, deep-pocketed incumbent in the general election.

Yeah, I’d say Gillespie’s open to fire from both ends of the political spectrum. One of his first prominent lobbying clients was Enron. One of the last causes he fought for in the Bush White House was the bank bailout. He’s been closely associated with Karl Rove for years. He was an important part of the Mitt Romney campaign brain trust.

Gillespie’s first hurdle will be the GOP nomination. The bad news is that the party has already decided to nominate its 2014 statewide candidates by convention rather than primary. VA GOP conventions have long been dominated by conservative activists; that’s how Ken Cuccinelli became the unopposed gubernatorial nominee last year, and also how he acquired that great statesman Bishop E.W. Jackson as his running-mate. The good news for Gillespie is that the convention’s in June, which won’t give rivals all that much time to build support to deny him the Senate nomination.

If he survives that test and doesn’t have to announce he’s for dismantling federal departments to get there (which wouldn’t go over real well in NoVa), he’ll have what Hohman calls a “steep slog” against Warner. GOPers seem to think Gillespie can wave away the lobbyist label by playing “so’s your old man” with attacks on new VA Governor Terry McAuliffe. I’m sure at this point in his life T-Mac would be happy to give VA Democrats the green light to go after Gillespie’s background with hammers and tongs.

At a time when so many pundits seem highly invested in the idea that the Republican Establishment is in the process of retaking control of the GOP, the Gillespie campaign will be a pretty good test of the proposition. Ol’ Ed’s so prototypical of the Establishment that if he loses the nomination or the general election, he’ll hurt his allies’ case for running much of anything.

UPDATE: Commenter sidney51 notes a MoJo piece on a VA congressional race that suggests the decision to proceed with a convention or a primary has yet to be made. But that decision is made at the district party level; the State Party has already issued the call for a convention on June 7 in Roanoke to pick a Senate nominee.

Ed Kilgore

Ed Kilgore is a political columnist for New York and managing editor at the Democratic Strategist website. He was a contributing writer at the Washington Monthly from January 2012 until November 2015, and was the principal contributor to the Political Animal blog.