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1. Brendan Sullivan (Williams & Connolly). He went to law school thinking he would never become a trial lawyer. If he had been right, Washington might never have known one of its all-time brightest legal stars. Sullivan changed his mind about trial work when he represented soldiers in the 1969 Presidio mutiny case while serving as a military lawyer. In that matter, 27 soldiers faced years in prison for staging a nonviolent sit-in. “It was an abuse by government that made me focus on the need for vigorous criminal defense,” Sullivan, 67, says today.
This year, Sullivan was at the center of the most talked-about criminal trial in Washington, representing then-senator Ted Stevens of Alaska against federal corruption charges. Sullivan’s arguments drew crowds of young lawyers eager to watch the master at work. The case against Stevens was thrown out after a series of foul-ups by the prosecution came to light. That misconduct never would have been revealed had Sullivan not rejected a plea deal earlier in the trial.
Sullivan—perhaps best known for his televised representation of Oliver North during the 1987 Iran-Contra hearings—shies from comparisons to the late Edward Bennett Williams, the founder of his firm and DC’s most fabled criminal defender. Yet it’s tough to think of anyone better suited than Sullivan to be Williams’s successor.
2. Seth Waxman (WilmerHale). There’s a lot of Beltway chatter about another possible vacancy on the Supreme Court, and former solicitor general Waxman is a favorite to fill it. But he’s so busy arguing in front of the justices that it’s doubtful he spends much time thinking about becoming one.
He has argued 55 times at the high court, with his 56th appearance scheduled for December 9 in Stolt-Nielsen v. Animalfeeds International. He’s arguing for all of the Stolt-Nielsen petitioners in the matter, which concerns commercial arbitration agreements. In November, he juggled two federal-circuit arguments in the same week—the first in a patent case for TiVo, the second in a patent-related case for Medtronic.
Waxman also has been at the forefront of Guantánamo Bay detainee issues. He won the landmark Supreme Court case Boumediene v. Bush in 2008, in which the court ruled that detainees have the right to challenge their detention in US courts.
3. Theodore Olson (Gibson, Dunn & Crutcher). Ted Olson is best known as the lawyer who won George W. Bush the presidency with his argument in the 2000 Supreme Court case Bush v. Gore, but the high-court advocate says the case he’s handling now could be the most significant of his nearly 45-year career. It’s the lawsuit he filed this summer in California federal court challenging Proposition 8—the state’s same-sex marriage ban.
Olson is both a legal and a Republican icon. He was an assistant attorney general in the Reagan administration, solicitor general under George W. Bush, and a leader in John McCain’s 2008 presidential bid—hardly an expected poster boy for gay rights.
Olson doesn’t see it as a partisan fight. That’s why he recruited New York lawyer David Boies—who argued for Al Gore in Bush v. Gore—to be his co-counsel: “I thought that if I combined myself with Boies, we could make the case that the issue was not a conservative or liberal or Republican or Democrat issue. It’s an issue of human rights and human dignity and decency and equality.” The case is set to go to trial in January.
Olson doesn’t have any Supreme Court arguments scheduled for this term, though he argued seven times before the justices last term.
4. Michele Roberts(Akin Gump Strauss Hauer & Feld). There are plenty of white-collar criminal-defense lawyers who prefer not to take civil cases. Roberts has an idea about why that is: “I guess they don’t want to see juries.” Tired of taking criminal cases that rarely go to court, Roberts—one of the city’s most feared trial lawyers—has no problem billing herself as a commercial litigator as well as a white-collar defender.
It’s easy to see why she has such a passion for going to trial. When Roberts—a natural in front of a jury—argues, there’s no doubt who’s controlling the room.
She took a turn arguing for the plaintiff’s side last year when she represented a small minority-owned company against defense contractor DynCorp for breach of contract and race discrimination. The all-white jury awarded her client $15 million in damages. She’s currently preparing to defend the energy company Valero against claims that it’s liable for the deaths of two boilermakers at a Delaware oil refinery. That case is scheduled to go to trial in February.
Despite the civil work, it’s doubtful that Roberts—who cut her teeth as a DC public defender—will ever shake her reputation as one of the best criminal lawyers around.
5. Sanford Ain(Ain & Bank). Washington’s top divorce lawyer is at heart a romantic. He talks about how much he loves his wife and how great marriage can be, and he’s quick to offer relationship advice. For someone who’s watched hundreds of unions break up, Ain evinces no cynicism—which is part of what makes him such an extraordinary lawyer. He’s not the vengeful type out to do battle; he says the courtroom is no place for families. Instead, he says, he settles 98 percent of his cases because it’s the most “respectful and dignified and discreet” way to handle divorces. It also allows him to take advantage of tax laws in ways that can save families money—creative strategizing that’s hard when a divorce ends up in court.
At $760 an hour, Ain is one of the priciest divorce lawyers, retained by celebrity clients and the very wealthy. But he says middle-income clients shouldn’t be deterred. For them, he helps devise an overall strategy and assigns another lawyer at his firm to handle the day-to-day work at less than half his own hourly rate.
Ain also specializes in breakups of a different variety: Doctors and lawyers who have used him for divorces often go back to him for help in splitting up their medical and legal practices.