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Kirkland Attorneys Arguing Back-to-Back Cases at Supreme Court

Dec. 9, 2019, 9:56 AM

Two Kirkland & Ellis attorneys will take the Supreme Court lectern on Dec. 10, arguing separately in back-to-back cases. For one, it will be his 99th appearance. For the other, his first.

Former Solicitor General Paul Clement will lead off on behalf of health insurers seeking nearly $12 billion in Obamacare payments from the federal government.

K. Winn Allen was appointed by the court to argue in the second case of the day, a sentencing dispute about what lawyers need to do to get more favorable standards of review on appeal for criminal defendants.

Having one firm argue cases in such proximity isn’t extremely unusual—so far this term, attorneys from Gibson Dunn, Goldstein & Russell, and the Stanford Law School Supreme Court Litigation Clinic have argued cases on back-to-back days. But Clement says it shows the deep bench the firm has in its appellate practice.

Allen said he and Clement are preparing for the cases separately. But he adds that “part of the privilege of working at Kirkland is being able work with Paul, who, in my view is the best Supreme Court advocate of our generation,” Allen said.

“I’ve definitely had the chance to pick Paul’s brain,” he added.

But even Clement—who is on the verge of being one of just a handful of advocates to argue 100 or more cases at the Supreme Court—said he’s got something to learn from Allen.

In a surprising turn, Clement recently got his first high court appointment, too. He will argue in support of the constitutionality of the Consumer Financial Protection Bureau, the brainchild of Democratic presidential candidate Sen. Elizabeth Warren of Massachusetts.

“There are some unique aspects of arguing in front of the court as a court-appointed amici,” where you don’t have to balance the interests of your clients, Clement said.

“I’m looking forward to learning from Winn’s experience as well,” Clement said.

Keeping Its Word

The stakes are high in both cases, but they’re different.

Allen described his case, Holguin-Hernandez v. United States, as a “technical, wonky sentencing issue” asking “what do you have to say and when do you have to say it” to get a more favorable standard of review on appeal.

The standard of review can affect the outcome of sentencing, meaning months and even years of prison can be on the line.

For Clement, about $12 billion hangs in the balance in a consolidated Affordable Care Act case, Maine Community Health Options v. United States.

Health insurers say they were promised federal payments to offset potential losses in providing coverage to those who were previously uninsurable. A later Congress refused to appropriate money to make those payments.

Beyond the financial stakes, the issue is “tremendously important because it’s really a case about the circumstances in which the government has to keep its word,” Clement said.

Out of the Blue

Allen’s appointment to argue came up because neither party—the criminal defendant nor the federal government—agrees with how the lower court resolved the dispute.

In this case, the government says reasoning by the U.S. Court of Appeals for the Fifth Circuit was wrong, but it didn’t affect the outcome of the case.

“The justice who has jurisdiction over the circuit from which the case arises takes the lead” on finding an attorney to take a so-called amicus appointment, Allen said.

“I got a call one day out of the blue from Justice [Samuel] Alito, who asked if I would do it,” he said. “I said, ‘Absolutely. I’d be happy to serve.’”

It’s not really a request you can turn down—"or frankly would want to say no to,” Allen said.

Tough One to Get

“The trend really has been to appoint younger lawyers,” Clement said. For a lot of lawyers, it’s a good way to get “their first opportunity to argue in front of the Supreme Court.”

The first argument is the hardest one to land, Clement said.

The first thing people want to know is “how many times have you done this?” Clement said.

“Most clients aren’t looking for the answer to be zero.”

To contact the reporter on this story: Kimberly Strawbridge Robinson in Washington at

To contact the editors responsible for this story: Jessie Kokrda Kamens at; John Crawley at