As Lt. Gov. Bill Bolling, right, enters the Senate Chambers he greets Sen. A. Donald McEachin-D-Richmond, left, and Sen. Ralph S. Northam-D-Norfolk, center, on January 11, 2012. (Tracy A. Woodward/The Washington Post)

Lt. Gov. Bill Bolling, the state’s multi-tasker in chief, had a few days over Thanksgiving weekend when about the only thing on his schedule was attending the football game between the University of Virginia and Virginia Tech in Blacksburg.

The man who has been juggling the part-time job of Virginia lieutenant governor with running for governor and working as a private insurance man took a breather — and took stock of his chances in 2013.

Some in Bolling’s small circle of advisers thought he could pull off a win against Attorney General Ken Cuccinelli II at the Republican convention in May. They were urging him to stay in the race. Others thought it was no use.

Bolling was expected to have clear sailing toward the GOP nomination after stepping aside four years ago to allow the current governor, Robert F. McDonnell, to run unopposed for the party’s endorsement. But Cuccinelli, who had said he intended to run for reelection, jumped into the governor’s race late last year.

Then, in late spring, Bolling had another setback. Cuccinelli supporters pulled off something of a coup, taking control of the Republican State Central Committee so they could change the nomination method in June from a statewide primary to a convention.

That gave a huge boost to Cuccinelli, a tea party hero, because conventions tend to be dominated by conservative party activists — the sort willing to travel to Richmond to devote a day to choosing a candidate. A statewide primary — open to all voters because there is no party registration in Virginia — would have been more favorable to Bolling, who shares many of Cuccinelli’s conservative views but has a more conciliatory style.

Bolling had known he faced an uphill battle since that about-face in mid-June. But he decided to push on, pinning some of his hopes on the presidential race. Bolling had been a Mitt Romney supporter since the former Massachusetts governor ran for president four years ago. And twice, Bolling was chairman of Romney’s Virginia campaign effort.

A Romney win could have helped Bolling in several ways, his advisers thought. There was a chance that McDonnell, who had been mentioned often as a potential running mate for Romney, would be given a Cabinet position. If McDonnell moved on before his term was up, Bolling would have finished it, enjoying the advan­tages of running as an incumbent.

Moreover, Bolling probably would have had a President Romney supporting his bid, advisers told The Washington Post. Romney endorsed Bolling while campaigning for president in Virginia, but he walked his comments back a short time later, apparently after having been reminded that the lieutenant governor had a Republican opponent.

Cuccinelli later made light of Romney’s “20-minute endorsement.” But Bolling campaign advisers said they were confident that Romney eventually would have come out for his longtime supporter.

“If Romney had won, that would have been a significant boost as campaign chairman for Romney,” said Boyd Marcus, a top campaign adviser. “It opened up the possibility of Governor McDonnell going to Washington. . . . If Romney had won, we certainly would have . . . had the president’s active support at that point. . . . That would have been a significant advantage.”

But Romney didn’t win. And Bolling, who had the backing of the business community and many establishment Republicans, was left to consider whether he could rally the grass-roots support needed to win at the convention, Marcus said.

Over Thanksgiving weekend, he had time to mull over that question with his closest adviser: his wife of 34 years, Jean Ann.

Weeks had passed since the election, but there was some urgency to make a decision. One week after Thanksgiving, hundreds of state Republicans would gather in Virginia Beach for an annual retreat — named the “Advance” decades ago to project a take-charge posture. Candidates for statewide office would pour money and energy into hosting hospitality suites at the posh Cavalier Hotel. The event functions something like a straw poll, with candidates’ strengths measured by such things as the quality of their bar offerings and prevalence of their lapel stickers.

The Bollings decided that they had to be “all out or all in” if they were going to go through with that weekend event, which begins Friday, Bolling told reporters at a news conference Thursday.

His aides had been split. Some thought there was still “a pathway to victory,” Marcus said. By Monday, after talking with aides and McDonnell, the Bollings made their final decision: He was bowing out.

Speaking to reporters Thursday, Bolling said the decision was the most difficult he had made in his life.

Known for his genial demeanor and self-deprecating humor, Bolling explained his decision by quoting an unlikely muse: Dirty Harry.

“A man’s got to know his limitations,” he said.