The following are (what I believe to be) the "most significant" Virginia Democratic campaign people ("staff" or "consultant," not candidate or elected official) of the decade. In rating "significance," I looked at the number of campaigns the person served on, the level of authority/responsibility they had, the importance of the elections they competed in, and the overall scope of their work. I also noted wins and losses in the entry for each individual but didn't really rank them according to their won-loss record. In addition to my own judgment, I asked a variety of Virginia Democrats what they thought of the people on the list, who they would add or subtract, etc.
Overall, I believe there are too many factors to simplistically say "they lost, they're an idiot; they won, they're a genius." Also, it should go without saying that this list isn't comprehensive, particularly in the earlier part of the decade where my knowledge is much more limited, so if you have any suggestions of people who should be added, please say so in the comments or send me an email. Also, please note that I haven't included committee chair (e.g., the excellent Peter Rousselot, who is retiring in early January) or leading bloggers (e.g., Ben Tribbett consulted and/or worked on numerous campaigns, for instance providing major assistance to Chap Petersen in his 2007 victory over Jeannemarie Devolites Davis). I also haven't included myself (I founded Raising Kaine, drafted James Webb and worked as his netroots coordinate; also consulted to Jon Bowerbank and Judy Feder). Anyway, enjoy (or not)! :)
Pete Brodnitz, Benenson Strategy Group: Polled for Terry McAuliffe (lost the primary) and Jody Wagner (won the primary, lost the general) in 2009. Also polled for Tom Perriello in 2008 (win), the DPVA in 2007 (gained seats), Jim Webb in 2006 (win), Tim Kaine in 2005 (win), and Rick Boucher (all wins). A winning track record overall.