Can Trump Lose the Cases Against Him in the Supreme Court and Still Win? By Jeffrey Toobin

Donald Trump stands under an umbrella in the rain.
Donald Trump has lost at every level of the judicial system in a pair of cases about his tax returns and financial documents, and he may well lose again—but a delay could be all he needs.Photograph by Andrew Harrer / Bloomberg / Getty
Here’s a tipoff for when a lawyer knows he has a weak argument: he resorts to the slippery slope. Based on Tuesday’s arguments before the Supreme Court in a pair of cases about efforts to obtain President Trump’s tax returns and other financial documents, his lawyers know that they are in trouble. Trump has lost at every level of the judicial system in both cases—and he may well lose again in the Supreme Court.

The first case concerns efforts by three congressional committees to subpoena long-sought documents regarding his finances and businesses, and the second one involves a subpoena from Cyrus Vance, the Manhattan District Attorney, who is seeking Trump’s business records and tax returns. In each case, the gist of the argument from Trump’s lawyers was the same. If the Court grants access to the documents, all future Presidents will be plagued with unreasonable demands for documents and testimony for all eternity. Patrick Strawbridge, who represented Trump in the congressional case, said, “The rule that the Court applies here will affect not only this President but the Presidency itself. The Court should deny the committees the blank check they seek and reverse the decisions below.” Jay Sekulow, who spoke for Trump against the Manhattan D.A., took an even more theatrical tack. “If not reversed, the decision weaponizes twenty-three hundred local D.A.s. It would allow any D.A. to harass and distract any President.”

The reason that Trump’s lawyers resorted to playing Chicken Little about the future implications of the cases is that the current facts of them—the issue before the Justices–are so straightforward. In the congressional case, several Justices pointed out that Congress has, on many occasions, investigated the personal financial dealings of the President. This happened most recently in the examination of President Bill Clinton’s involvement in the Whitewater land deal, in Arkansas. True, the Supreme Court never evaluated the propriety of that investigation, because Clinton ultimately turned over his business records. But no one suggested that Congress lacked the authority to look into the issue. Strawbridge, along with a representative of Trump’s Justice Department, said that the subpoenas served no legislative purpose—that they were designed purely to obtain dirt on the Democratic House of Representatives’ bête noire. “These subpoenas fail every hallmark of legitimate legislative investigation,” Strawbridge said. But Justice Ruth Bader Ginsburg, and even some conservative Justices, said that it wasn’t up to the courts to cross-examine members of Congress about what their ultimate purposes are. If they said that they were considering legislation—here, regarding conflicts of interest in the executive branch and Trump’s dealings with Russia—that’s usually good enough for the Justices. “Why should we not defer to the House about its own legislative purposes?” she asked.

Sekulow had a harder time with the Court, because he was making an even more expansive claim: that the District Attorney had no right even to investigate Trump while he was President. “The President is not to be treated as an ordinary citizen, and it’s a temporary immunity while in office,” he said. But Justice Stephen Breyer responded that the Court had ordered Bill Clinton to give a civil deposition in the Paula Jones sexual-harassment case against him. That was a great deal more burdensome than turning over existing documents, which are in the hands of Trump’s accountants, anyway. (Since the subpoena is actually directed to Trump’s accounting firm, Trump himself is not required to do anything at all in response to it.) Sekulow’s response—that Trump would have the burden of reviewing the documents with his counsel—seems weak.

It’s entirely possible, though, that Trump can win these cases by losing. The Court could reject Sekulow’s broad claim of immunity, but send the case back to the lower courts to evaluate the subpoena under a new standard. That would certainly delay the resolution of the case—and the production of Trump’s tax returns—until after the election, in November. And that is certainly what Trump wants most of all.

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