The only way for Bolling to win would be for the McAuliffe campaign to totally collapse. Should Bolling actually ever mount a serious campaign with a chance of winning, it would require Terry to run third!
Do the math. Cuccinelli has the anti-abortion base of the GOP. By backing McDonnell's record tax increase in an election year, Bolling has sacrificed any credibility with the Republican anti-tax base. The business base of the party is leery of Cuccinelli but they have more money than votes. Meaning: Cuccinelli has most of the GOP base locked up on ideological grounds.
He basically has 30-35% locked in a three-way race unless something unexpected happens. In large measure, this is now a personal base as well. They are very pro-Cuccinelli. Further meaning: There is no way Bolling can get into the race with a reasonable expectation of shaking any useful number of these voters loose from the K-Man. If Bolling is going to have any chance of winning, he has to shake the McAuliffe political tree and get voters to fall off.
Think Democrats will abandon their party's choice for governor, with all the problems that creates down ticket?
Then you think Bolling has a chance.