The first was Vermont's campaign finance law setting the lowest contribution limits in the country _ shot down by the U.S. Supreme Court.
The same fate befell the state's attempt to restrict drug company efforts to collect data on doctors' prescribing habits. On a 6-3 vote, the justices said Vermont's law was an unconstitutional infringement on free speech by drug and data collecting companies.
Now, in yet another case that has garnered national attention, the office of Vermont Attorney General William Sorrell has suffered a stinging defeat, this time in a federal trial over the state's bid to close the Vermont Yankee nuclear plant.
Some observers are starting to see a pattern _ one in which Sorrell and his team have gone to the legal big leagues three times and fallen flat on each attempt.
"The state now has sort of a reputation in the 2nd Circuit and the Supreme Court of not having their act together," said Patrick Parenteau, a former state commissioner of environmental conservation who is now a professor at Vermont Law School.
The losses have been costly for Vermont. The state paid out about $1.5 million to the plaintiffs in the suit that resulted in its campaign finance law being overturned in 2006. In the prescription data case, Vermont already has paid more than $1.7 million to a pharmaceutical trade group and is expected to have to pay $3.8 million to cover legal costs incurred by the data companies.
The total, at least $7 million, nearly equals the roughly $8 million annual budget of Sorrell's office. The payouts will come from the state's $1.4 billion general fund.
Sorrell, 64, was appointed attorney general in 1997 by the governor at the time, Howard Dean, and has been elected to seven two-year terms since then. He attributes the court losses essentially to a string of bad luck, some of it resulting from trying to defend Vermont's federal laws before a more conservative federal judiciary.
He also maintains that his office has its share of victories, including a 2007 case in which Vermont defended its effort to follow California in adopting new and more aggressive car fuel economy standards.
"That we tried successfully, and it now is the national standard for emissions from autos, and that will have a profound impact on the quality of our air and fuel efficiency," Sorrell said.
In the three big losses, some lawyers noted, Sorrell's office was trying to defend state legislation that courts found simply didn't pass constitutional muster.
"They've all been tough cases. Our Legislature has pushed the envelope in a number of policy issues," said Sandra Levine of the Conservation Law Foundation, which supported Vermont in both the auto emissions and Vermont Yankee cases.
Sorrell, a Democrat who was re-elected with 62 percent of the vote in 2010, appears to be on solid footing politically as this year's election season approaches. Given his closeness to Dean, still a power broker in the state, Democrats are unlikely to challenge Sorrell in a primary.
And Republican criticism likely would be muted by the fact that the three biggest cases lost by Sorrell's office came while trying to defend legislation most members of that party opposed.
Sorrell acknowledged that, with U.S. District Judge J. Garvan Murtha's decision last week that Vermont Yankee can stay open over the state's objections, his office is coming off a loss.
"I respect the right of people to Monday morning quarterback," he said.
In at least two of the cases, some found fault in the courtroom performance of Sorrell and his team.
The book "A Good Quarrel: America's Top Legal Reporters Share Stories from Inside the Supreme Court," edited by Timothy R. Johnson and Jerry Goldberg, said Sorrell himself was caught flat-footed when trying to defend the state's campaign finance law before the Supreme Court.
"For twenty minutes, Sorrell would have a face-to-face chance to persuade any justices who might be sitting on the fence. Unfortunately for Vermont, Sorrell's appearance before the Court proved rocky," the book said.
As he began his argument, Sorrell was hit with a barrage of tough questions from Chief Justice John Roberts. The book's account says, "Off balance from the start, Sorrell never fully recovered, as other justices picked up where Roberts left off."
Before that Supreme Court appearance, legal observers said Vermont faced an uphill battle in persuading the increasingly conservative court to leave Vermont's limits on campaign contributions in place. It was largely the same court, Sorrell noted, that later decided the Citizens United case, a 2010 decision that critics say has unleashed a torrent of corporate money into trying to influence elections.
In a two-day preliminary hearing in June and a three-day trial in September on the Vermont Yankee case, other senior lawyers in Sorrell's office presented the evidence and arguments. Several observers said they were outclassed by a smoother and more high-powered presentation put on by the legal team for plant owner Entergy Corp., led by Kathleen Sullivan.
The mellifluous voice of Sullivan, a former Harvard Law School professor and Stanford Law School dean sometimes mentioned as a candidate for the U.S. Supreme Court, carried to the back of the courtroom, while spectators had to struggle to hear the arguments of Assistant Attorney General Bridget Asay, who handled part of the state's case.
Parenteau, who attended part of the trial in Brattleboro and has blogged about the Vermont Yankee case, faulted the state for breaking up its presentation among a team of lawyers, adding that while Entergy used more than one lawyer, Sullivan clearly led the presentation.
"She had a very powerful, cohesive, seamless narrative _ the law, the facts, the policy, everything. The state's case was more fragmented. They didn't have a clear lead who could go one on one with Sullivan," Parenteau said.
Sorrell said he expected Entergy had spent more on legal fees than the entire annual budget of his office _ about $8 million. But he said his office has always reaped more in judgments and settlements than it has paid out. Deputy Attorney General Janet Murnane provided a spreadsheet showing the office had recovered nearly $82.4 million in the past 30 months.
An Entergy spokesman could not say whether the company would try to recover those costs. The company's Chanel Lagarde said, "Right now our focus is on reviewing the court's decision."