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Last March, the case—in which Clifford was the lead plaintiff’s attorney—settled for $1.2 billion, an agreement that will enable a group of insurance companies to recover some of the property damage claims they paid as a result of the 9/11 attacks. The story of the litigation sheds light on the background of the terrorist disaster—though many of the details are still classified. But it also offers a picture of the style and tactics of Bob Clifford, the compact, no-nonsense Chicagoan who has made himself into arguably one of the top aviation litigators in the nation.
At 59, Clifford has represented families against the airlines in every major crash over the past three decades, winning (or settling) them all. Year after year, his 20-lawyer office is at or near the top of Chicago Lawyer magazine’s survey of Illinois firms that won the most settlements above $1 million.
Coming from a working-class background, Clifford views himself as a little guy battling corporate wrongdoers and their high-paid legal defenders—the white-shoe corporate bar who went to the best law schools in the country and probably wouldn’t have hired Clifford as a paralegal when he graduated from DePaul. At around five feet seven, he’s not a physically commanding presence, and his speaking style can lapse into the “dese, dem, dose” idiom. Strip away his tailor-made suits, cuff links, and polished wingtips, and you’ll find a scrappy South Side Irish kid spoiling for a fight.
Juries empathize with that regular-guy image, says Thomas Demetrio, one of Clifford’s close friends and a friendly rival at the firm Corboy & Demetrio. “Bob’s way about him is real—it’s not pretend, it’s not acting. What you see in Bob is the way he is in the courtroom,” says Demetrio.
Clifford himself has a characteristically straightforward explanation for his success: “I learned a long time ago that persuasion is fact based,” he says. “I can show you dozens of lawyers who think that they can get by with their silver tongues, and they lose all the time to someone who’s better prepared and works harder.”
Preparing for the damages trial of Rachel Barton Pine, the acclaimed violinist who lost her left leg in a 1995 Metra train accident, Clifford got transcripts of opening and closing statements made by his opposing counsel, C. Barry Montgomery, at other trials. As Clifford studied the dozens of transcripts, he found that Montgomery often used the same catch phrases and stock lines. So Clifford used them in his opening argument while Montgomery watched in surprise. Clifford wound up winning a $30 million jury verdict. Recalls Montgomery: “When I was sitting there listening to Clifford’s opening statement, I thought it was me up there talking.”
In 2005, after a Southwest Airlines jet skidded off a snowy runway at Midway Airport and crushed a car parked at a street intersection, killing six-year-old Joshua Woods, of Leroy, Indiana, Clifford devised an ingenious legal argument to get the case out of federal court and into state court, his preferred venue. He convinced a judge that the plane’s pilot had broken state and city laws—not federal laws—because the pilot was driving on Central Avenue and 55th Street without a valid driver’s license or city vehicle sticker. Clifford settled the case for an undisclosed sum “in the millions,” he says.
But in Clifford’s long and impressive docket of cases, the 9/11 litigation on behalf of the insurance companies stands as one of his most significant. In legalese, the matter is known as a subrogation case. Put simply: If, say, a driver runs a red light and crashes into your car and your insurance pays for the repairs, your insurer can sue the careless driver to recoup (presumably from his insurer) the money it paid on your behalf. Over time, Clifford’s case grew from a technical fight over insurance reimbursements into a broader battle over whether the airlines and the security companies should have been more vigilant in thwarting the terrorists. Clifford maintains that the plaintiffs unearthed facts about security failures on September 11th that were missed by the blue-ribbon 9/11 Commission and by Congress in its investigations. “9/11 was not only foreseeable, it was preventable,” says Clifford. “Think about it—19 out of 19 terrorists got through that day. Actually, it was 21 out of 19, because two of ’em got through twice. Don’t you think one of them would’ve been stopped?”
For now, the trove of materials remains under seal; the airline defendants and the government argue that the information, if released to the public, could help potential terrorists. But Clifford says he hopes that one day the full story will come out. “I think in many sectors of America, corporations escape accountability because there’s no transparency,” he says. “The more transparency we have, the greater accountability it breeds.”
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Going on nearly ten years, the consequences of the attacks on September 11, 2001, are still reverberating in Manhattan. Beyond ground zero itself, the wounds have perhaps resounded most loudly in the Manhattan courtroom of Alvin K. Hellerstein, the federal judge who has overseen the collection of lawsuits arising from 9/11. The cases—many now settled—cover a wide landscape. Some were wrongful death actions filed by families who didn’t participate in the September 11th Victims Compensation Fund but who lost relatives in the attacks. Some were suits by ground zero workers who claimed they developed respiratory and other illnesses during the recovery efforts. And some were subrogation claims against the airlines and the airport security firms to recover property damage losses from the destruction of the twin towers and nearby buildings.
That’s where Clifford came in. As it happens, he was well positioned to become a slice of 9/11 history even before he found himself in the eye of the subrogation storm. Shortly after the attacks, Clifford was recruited to head the American Bar Association’s special task force on terrorism and the law. In the ensuing months, the task force weighed in on the USA Patriot Act, the Victim Compensation Fund, and various 9/11-related laws enacted by Congress.
Sometime in mid-2004, Clifford got a call from a top legal executive at Industrial Risk Insurers, which had insured the 7 World Trade Center Building for Silverstein Properties. After the structure was destroyed in the attacks, IRI paid Larry Silverstein, its leaseholder, more than $860 million to settle claims on the property. Now IRI wanted to recover some of that money by suing the airlines and their security firms.
Clifford wasn’t sure he wanted to get involved. A subrogation suit would be big and complex. Litigation this massive would cost his firm millions of dollars and take years to resolve. But the payout could be huge. (Like other top trial lawyers, Clifford works on a contingency-fee basis. Clients pay no money up front but give the firm a percentage of any award in a settlement or verdict, usually one-fourth to one-third.) The case was risky, but ultimately Clifford couldn’t refuse.
He filed suit on September 10, 2004, and not long after, the other lawyers for the plaintiffs picked him to lead the court battle. Why Clifford? Mainly because he was a personal injury lawyer with a long track record of bringing the airline companies to their knees. “At the end of the day, this was an aviation case—an aviation case involving property damage,” says Steven Badger, a Dallas attorney whose firm, Zelle Hofmann, was among the principal firms representing the plaintiff insurers.
To make their case, Clifford and his legal team had to establish that the airlines and their security companies could have anticipated the attacks—an allegation they had always denied. Originally, even Clifford doubted the terrorists could have been spotted. A week after the attacks, he told the Chicago Sun-Times, “There’s no evidence that the weapons brought on board were anything other than those allowed under FAA regulations. You may never have proof of actual negligence here.” That, more or less, was the defense argument in the case: The airlines and airport security couldn’t possibly have foreseen that planes would be used as missiles. “Let’s face facts,” says the defense attorney who asked to remain anonymous. “This was 2001. Nobody saw this coming.”
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