When you’re the most prominent and powerful plaintiffs’ attorneyin the land, winning hundreds of billions of dollars for yourclients, you definitely qualify as a legend—or rather, a bogeymanwho undoubtedly has haunted the dreams of many a carrierexecutive.

Richard “Dickie” Scruggs may now be serving time at a federalprison camp in Alabama for his role in bribing two Mississippidistrict court judges, but prior to his fall from grace hedominated courtrooms for decades, playing a significant role in notone, not two but three of the most important and costly civildisputes of all time: those revolving around assigning liabilitiesfor tobacco, asbestos and Hurricane Katrina.

Indeed, following Katrina, Scruggs became a symbol of anaffirmation of policy language—specifically a certain tongue-tyingclause in homeowners’ policies used by plaintiffs’ attorneys tofuel misinterpretations and villainize insurers. Through hiscrusade against insurance companies, Scruggs ironically ended upcementing the very policy language he attempted to use as a weaponagainst insurers.

Scruggs attacked the insurance industry with hundreds oflawsuits following the hurricane, alleging insurers underpaid andused the “anti-concurrent causation clause” to inappropriately denypayments to policyholders for wind damage.

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No company was targeted more than State Farm. Flanked by formerindependent claims adjusters Kerri and Cori Rigsby, Scruggsasserted he had proof within thousands of documents that State Farmhad altered claims reports.

These “whistleblowers,” he said, stole State Farm documents thatallegedly proved the insurer fraudulently reduced wind losses byclaiming damage was from flooding—a peril not covered by a standardhomeowners’ policy—and fraudulently shifted losses to the NationalFlood Insurance Program.

Scruggs, himself a victim of Katrina, launched a “populist,political fight—not a legal fight”—against insurers, says AlanLange, who covered the lawsuits on his blog Y’all Politics andpenned the book “Kings of Tort” about Scruggs’ subsequentdownfall.

“It was a professionally run public-relations effort,” saysLange of Scruggs’ tactics—and he had powerful allies. Hisbrother-in-law is Trent Lott, then a U.S. senator. AndMississippi’s state attorney general was threatening the criminalprosecution of insurance executives.

“I don’t think he ever meant to see the inside of thecourtroom,” Lange says of Scruggs. “He just expected [insurers] tothrow up their hands and say, ‘Make it stop.’”

Insurers were losing battles in lower courts on whether stormsurge was part of the flood exclusion and/or the anti-concurrentcausation clause in homeowners’ policies. Judges called policylanguage ambiguous and unenforceable.

Outcomes were fueled by misinterpretation, jury pools of stormvictims and the difficult task of assessing damages to “slabcases”—homes that were battered so hard by Mother Nature that onlya concrete slab remained.

There were some cases in which insurers deemed it a betteroption to settle than fight a prolonged legal battle; Scruggs mademillions from those cases, although that payoff was likely not asbig as he’d hoped, says attorney David Rossmiller of Dunn CarneyAllen Higgins & Tongue LLP in Portland, Ore.

Rossmiller says Scruggs made a few key miscalculations regardingthe willingness of certain insurers—especially State Farm—to fightto defend the language in their policies.

“Insurers were very vested in upholding the language andconquering misconceptions because it affected their profitability,”says Rossmiller, whose papers published on the anti-concurrentcausation clause were often cited by judges as insurers took theirfight to higher courts.

Making a long, convoluted story of litigious motions and appealsshort, in the end insurers came out on top in the question of windvs. water.

“It came down to the words on paper,” says Rossmiller.Regardless of the policy language, the clause, he adds, “can onlybe manipulated so far.”

When the media, political and public-relations storms againstinsurers dissipated, he adds, policies still contained languagedriven by court precedent and created for judges, not amateurreaders of litigation.

“Just because it may sound confusing—or the language is puttogether poorly in some cases—doesn’t make it ambiguous,” saysRossmiller. “It’s still all right there.”

Courts determined Katrina did not involve concurrent orsequential damage. Each force acted separately and caused separatedamage. Insurers are responsible for wind damage; they are notliable to pay for water damage.

Scruggs, who began his legal career defending insurancecompanies, is scheduled to be released, stripped of his lawlicense, in 2015—about the time that some observers predictnanotechnology will become “the next asbestos.”