One attorney is known for his measured, authoritative approach, the other for a brash, confrontational style. And when the Affordable Care Act brings both of them back before the Supreme Court on Wednesday, these differences may be on display as much as their legal points.

In what’s arguably the most important case of the court’s term, Michael Carvin will argue for plaintiffs seeking to upend a fundamental aspect of Obamacare, and Solicitor General Donald Verrilli Jr. will again defend the government. Both are hailed as brilliant litigators steeped in case law, and their first round in 2012 concluded with each man able to claim a victory of sorts.


This rematch is unlikely to end in the same way.

“The operation was a success, but the patient died,” Carvin told others after the justices ruled three years ago. They’d bought his argument that Congress didn’t have a constitutional right to mandate that Americans buy health insurance. But their 5-4 decision upheld the law on the grounds that Congress could tax people who didn’t get coverage.

The outcome was a surprise for many given the hostile questions lobbed at Verrilli and his halting performance, which was epitomized by the moment when he literally choked on a sip of water. Yet his nuanced definition of mandate as a “tax penalty” appealed to Chief Justice John Roberts and ultimately saved President Barack Obama’s signature measure.

The arguments in King v. Burwell won’t hinge on lofty constitutional principles but rather on the intent of the law’s text as embodied particularly by five words: “Exchange established by the State.” The two litigators declined to be interviewed in the days leading up to the big case, leaving colleagues and friends to speak for them. They describe stark contrasts — not just in delivery but in temperament and philosophy, too.

‘MIKE’ CARVIN

The weekend before those first ACA arguments back in 2012, Carvin’s firm happened to be hosting an event at its Washington office. “There’s a crazy homeless man outside the building, talking to himself,” a woman reported to the front desk, as his Jones Day colleague Noel Francisco recalled.

It was Carvin, preparing for the hearing before the high court. In a baseball cap and overcoat, he was pacing the sidewalk, asking himself questions and then answering them out loud, all the while puffing on a cigar.

Carvin’s approach in the courtroom isn’t exactly refined either: Friends and professional foes alike use words like “brusque” and “dismissive” to define his style, though all agree that he’s effective — and entertaining.

“He is a plain-speaking person. You’re not going to get lost,” said McKenna Long & Aldridge’s Robin Conrad, who collaborated with Carvin on work for the U.S. Chamber of Commerce. “He knows the cases inside out and backwards, but he’s not going to come across as an academic and smother you with case citations.”

A native of Bronxville, New York, the 58-year-old Carvin likes to downplay his academic credentials and jokes that he went to a “party school in Louisiana.” He followed his days at Tulane University with a law degree from George Washington University and then worked in the Reagan Justice Department before starting his own unabashedly conservative firm in D.C.

He gradually built a reputation as one of the most persuasive antagonists of federal power . He argued Bush v. Gore before the Florida Supreme Court and scored a Supreme Court victory related to the Sarbanes-Oxley Act that preserved the separation of powers in executive branch appointments. Although Carvin was not the lead attorney in the first Obamacare challenge — that fell to the elegant Paul Clement — he did offer one of the key arguments against the individual mandate.

“He was very passionate,” said Karen Harned, executive director of the National Federation of Independent Business, which hired him for the case after he wrote a brief for a group of former attorneys general. “He was all in on the substance as far as truly believing that this was inappropriate.”

His rhetoric is colorful and relies heavily on metaphor. Classifying the individual mandate as a tax is a “Frankenstein monster” of a rationale, Carvin told the radio host Laura Ingraham in a post-ruling interview. The court’s deference “to democracy,” he added, was like “deferring to Bernie Madoff in the name of free enterprise.”

While Carvin can be quick to criticize ideas he deems inferior, colleagues say his warmth comes out when he talks about his two children or his other passions, golf and fishing.

Even after Obamacare’s constitutionality was upheld, Carvin knew there’d be other lines of attack. But at least one attorney close to him has been vocal about the perils of cutting Obamacare benefits now that the law has been implemented. His wife, who for years lobbied for the American Medical Association and today is a policy strategist for Fight Colorectal Cancer, analyzed the 2014 elections and predicted a political backlash should Republicans use their majority to try to force repeal.

“It is unlikely that Americans will support members of Congress who drop access to health care to individuals and families who are eligible for coverage as a result of the ACA,” Margaret Carvin wrote.

‘DON’ VERRILLI

The solicitor general usually leaves the brief-writing to his staff, checking and editing their work toward the end. But for King, Verrilli wrote most of the brief himself, crafting it over several days and nights, Justice Department spokesman Brian Fallon said.

The case might be more important to him than almost any other, friends and allies say. Yet not because he needs vindication, they stress. Criticism of his performance during the first Obamacare case was way overblown, in their view. And in the end, he did win.

Michael Carvin will argue for plaintiffs seeking to upend a fundamental aspect of Obamacare. | Getty

Rather, Verrilli is particularly devoted to this case because extending health care to millions “is the kind of thing that people like Don go into government to do,” said Mark Schneider, general counsel for the International Association of Machinists, who has seen his longtime friend tear up when talking about his role in preserving the ACA. It’s like “a missing piece of the New Deal program.”

That liberal sensibility runs deep in Verrilli, a graduate of Yale University and Columbia Law School who clerked for Justice William Brennan in the 1984-85 term. Accompanying it is what former White House counsel Kathy Ruemmler calls a “fierce intensity,” which he brought to bear while arguing many pro-bono death penalty appeals while a partner at Jenner & Block. In one, he appeared before the Supreme Court on behalf of a Maryland man who Verrilli believed had suffered from incompetent counsel during trial. The justices agreed and overturned the capital sentence.

Not all of his private work reflects causes, however: In 2005, he successfully argued on behalf of the music industry that the file-sharing service Grokster could be held liable for copyright infringement.

Verrilli joined the Justice Department in 2009, handling national security issues. He then served as deputy White House counsel before Obama nominated him to replace Elena Kagan as solicitor general four years ago. His demeanor in court as the government’s lawyer has become, perhaps by necessity, more restrained and less impassioned.

Obama and Verrilli formed a “deep mutual respect” while he worked in the White House, Ruemmler said. She remembers the two parrying over whether the government should file a brief supporting the challenge to California’s gay marriage ban, with a “lengthy discussion about the equal protection clause.” Verrilli ultimately satisfied the president that it was in the federal interest to weigh in.

Verrilli, 57, is from a family of attorneys and government officials. His father was a lawyer and and his mother served as the chief executive of Wilton, Connecticut, the town where he grew up. His wife, Gail Laster, is also a lawyer and currently director of consumer protection at the National Credit Union Administration. Their daughter works as a paralegal in New York.

His parents worried that his 1988 marriage to Laster, who is black, would hamper his career. “It was a reasonable fear, I guess, but they weren’t right about it,” Verrilli told NPR’s Nina Totenberg in 2012. Indeed, Verrilli was thought to be on the short list last year to succeed Eric Holder as attorney general, until federal prosecutor Lorretta Lynch got the nod.

At home Verrilli likes to garden and cook big Italian meals, although he’s a regular at Tosca Ristorante in downtown Washington. But it’s a safe bet that Tuesday night, he’ll be eating a modest grilled salmon. It’s his pre-argument tradition.