Some might see this as jockeying for a VP slot, rather than a direct shot at Hillary
Flow of money will probably be the test of Webb's staying power
According to a report picked-up on the AP, "... Former Virginia Sen. Jim Webb has formed an exploratory committee to consider a Democratic presidential campaign in 2016. *** It's the first official step in what could be a challenge to Hillary Rodham Clinton if she seeks the White House again. *** Webb announced a website for his exploratory committee in a message posted from his Twitter account late Wednesday. He says many Americans believe the U.S. is 'at a serious crossroads' and the solutions 'are not simply political, but those of leadership.'..." (See "Jim Webb forms exploratory committee for White House" 11-20-14, WUSA-9 [http://www.wusa9.com/story/news/2014/11/20/jim-webb-exploratory-committee-white-house-presidential-campaign-va/19312571/]).
Not long ago when Jim Webb first mentioned a possible run for the White House, at least one longtime Democrat commentator said, "Democrats uneasy about a Hillary coronation may have help on the way from former Virginia Senator James Webb... , who[has given speeches that sound like they are from] a populist perspective, slightly right of center where Webb, a former Republican, is most at home and often straddles the two parties.... [Also in the recent past] Webb served up a scathing critique of the administration’s foreign policy, calling it 'a tangled mess of what can only be called situational ethics.' He said there hasn’t been a clear statement of principles since the end of the Cold War, and 'not surprisingly the American people have become more cynical about their leadership in both parties.'... [But he also] warned against getting entangled on the ground in the “ongoing nightmare” that is Syria...." (See "Wait a Minute, Clinton Coronators—Here Comes Jim Webb" by Eleanor Clift, 9/26/14, The Daily Beast [http://www.thedailybeast.com/articles/2014/09/24/wait-a-minute-clinton-coronators-here-comes-jim-webb.html]). Clift also noted that "For Webb, there is an opening for someone with a strong military background and no real ties to the Obama administration that would constrain him from an unvarnished assessment of the Democratic Party’s policies and performance. The author of 11 books, Webb’s new memoir, I Heard My Country Calling, may have stoked the fires of his political ambition once again..."
For Webb. money is very much the key to unlock any showing by him in 2014. "Dr. Bob Roberts, political science professor at James Madison University, said in order for Webb to even make it to the primaries, he must use the exploratory committee to see if he can raise enough money from leaders in his own party to run a campaign.... 'Will the money people view him as an option? If he doesn't get money, he's dead. This is simply the ability to say will some people out there, maybe some PAC's, maybe some of these independent groups, who are really opposed to Hillary, would they give him money as a way to stall her. That's what it comes down to,' said Roberts...." (See "Jim Webb Eyeing Possible Presidential Run" 11/20/14, WHSV [http://www.whsv.com/news/headlines/Jim-Webb-Eyeing-Possible-Presidential-Run-283365481.html]).