Nearly all cases have been decided by the powerful D.C. Circuit Court of Appeals, which hears most challenges to newly minted agency rules.

Those judges have repeatedly called the EPA's legal justifications thin, some so laughable they would only make sense if presented in a fairy tale:

When the EPA tried to argue that the word any in existing air pollution law did not literally mean "any," the court said that would make sense "only in a Humpty Dumpty world."

When the EPA tried to alter mercury emission controls on certain power plants, the court compared its legal logic to the Queen of Hearts, the Alice in Wonderland character who makes one arbitrary decision after another.

When the EPA essentially lowered a water pollution limit by reinterpreting a law requiring "daily" monitoring to allow "seasonal or annual" monitoring, the court said this was absurd: "Daily means daily, nothing else."

The EPA's biggest loss in the courts came last year in the case brought by Massachusetts on climate change. The agency had argued that it did not have the authority under the Clean Air Act to regulate carbon emissions and other greenhouse gases, and therefore could not use the law to combat global warming.

The U.S. Supreme Court rejected that contention, saying the evidence of climate change was overwhelming and that the EPA did have the authority to regulate greenhouse gases, regardless of doubts about causes and effects.

"That EPA would prefer not to regulate greenhouse gases because of some residual uncertainty . . . is irrelevant," the court wrote.

James Pew, a Gladwyne native and a lawyer for Earthjustice, a firm that represents environmental groups, said the EPA was prone to issue rules that courts later would find arbitrary.

"I think EPA was being reckless," he said. "There were only a few outcomes, and all of them were good for industry. If they managed to get a rule passed through judicial review, they would get an industry-friendly rule on the books. If it got thrown out, industry would get a delay in having to clean up its emissions, and that would be good for industry."

Either way, the consequences were severe, said Pew. "Whenever EPA loses one of these cases, the people who have to breathe toxic air take the hit because EPA has to go back and write another rule. Years go by."

Rep. Henry Waxman (D., Calif.), who chairs the House Oversight Committee, said: "This administration's pattern of issuing rules that don't stand up in court has caused multiple serious harms" - to public health, taxpayers and industry.

Jeffrey Holmstead, a former EPA assistant administrator who was a chief architect of the Bush air pollution agenda, said the courts ruled incorrectly.

The losses, Holmstead said, were unexpected, in part because the courts had historically deferred to EPA rulemaking, except in extreme circumstances.

"If the D.C. Circuit had reviewed these cases the way they had done in the previous 15 years, those rules would have been upheld," he said. "Some of the decisions were not only a surprise but don't make any sense as a matter of administrative law."

But three former EPA political appointees, including former Administrator Christine Todd Whitman, said many court decisions did not come as a surprise. They said lawyers in the EPA's Office of General Counsel had warned that several administrative rules were too arbitrary to survive a court challenge.

"The General Counsel's Office offered very frank advice," former Associate Deputy Administrator Jason Burnett recalled.

EPA Administrator Stephen L. Johnson, who signed many of the rules that the courts have thrown out, blames a Democratic-controlled Congress for failing to adopt a comprehensive new pollution law. If Congress does not adopt new laws to address 21st-century pollution issues, Johnson said, the EPA will continue to be caught in a cycle in which it writes administrative regulations that are inevitably challenged in court by industry or environmental groups.

"EPA can do it reg by reg, year by year, but as I look as to what's best for the nation, let's have Congress cut to the chase, make some important decisions," he said. Otherwise, "it will be decades before our nation fully addresses these, given the litigation issues, and I have grave concern."

Sen. Tom Carper (D., Del.), who chairs the Senate's clean air subcommittee, said comprehensive legislation could have been passed, but the Bush administration simply refused to compromise.