Cuccinelli also accepted gifts from Williams and owned stock in his company, though an investigation last week found he did not violate the state's conflict of interest laws.
"This is a no-win situation for Cuccinelli," said Democratic strategist Mo Elleithee, a veteran of Virginia campaigns. "If Bob McDonnell somehow is able to remain in office, he'll be a daily reminder of Cuccinelli's own ethical challenges with Star Scientific. If Bolling assumes the governorship, not only will Cuccinelli still be under an ethical cloud, but the new governor will be a daily reminder of how even mainstream Republicans view him as too extreme."
Bolling's comments over the last few months to a spate of news organizations seem tailor-made for negative television ads and mail pieces: "Don't believe us? Here's what Virginia's own Republican governor had to say about Ken Cuccinelli ..."
Bolling has even left the door open to voting for Cuccinelli's Democratic opponent, Terry McAuliffe, who, he kindly pointed out, "takes a more pragmatic approach to politics and to governing."
At the moment, it doesn't seem the Bolling-as-governor scenario will come to pass.
Bolling is close with McDonnell and certainly isn't angling for the job. Though he's had designs on the governorship for years, taking over for McDonnell in the wake of scandal, with regular legislative business wrapped for the year, isn't much of a prize. Nor could Bolling suddenly decide to run for a full term -- the filing deadline to run in November passed in June.
Barring another devastating disclosure about the investigation, the only real pressure point for McDonnell as he braces for a tough final six months in office would be a chorus of resignation calls from legislators in his own party. But so far, not a single prominent Republican has called for McDonnell to leave office.
Meanwhile, McDonnell has hired a Washington-based crisis communications consultant and former U.S. attorney to fight back against federal investigators, and some of his supporters launched a legal defense fund last week.
Those aren't the actions of a man preparing to step aside.
But if he does, Cuccinelli and Virginia Republicans might only be trading in one headache for another.