What does Obama need?
1. Military expericen
2. Foreign policy savvy
3. Understanding of the Middles East
4. Someone who can help him win in VA/NC
5. A pugnacious vet who can rip John McCain apart
The man who can deliver for Obama is Jim Webb. A Vietnam war vet turned Navy Secretary under Reagan turned swing state Senator. Webb also oozes testosterone his presence on the ticket would add a much-needed macho boost for the Democratic Party. Webb's military heroism would inoculate from backlash when he attacks John McCain.
Webb also adds the right experience to the ticket. His knowledge of Iraqi history is simply unparalleled in the U.S Senate. On Meet the Press and other pundit shows he's dominated his Republican jousting partners. He wouldn't be cowed in a debate against whomever the GOP nominates for VP.
...and we don't have to worry about what would happen if he won...there are still tons of candidates that could keep the seat in VA...like Tim Kaine. I also would hope that Webb could talk Obama out of ending the space program (which might swing me...space is cool)