In his effort to defend himself against any and all investigations, President Donald Trump and his lawyers have made a number of novel, often outrageous, arguments asserting he has nearly complete immunity from oversight. He rejects subpoenas seeking his financial records, testimony from administration officials or documents from federal agencies. He asserts executive privilege on the actions of nongovernment employees. And he denies the legitimacy of the impeachment inquiry underway by the House of Representatives into his actions involving Ukraine. Some judges have displayed shock at the “extreme” legal positions, as U.S. District Judge Beryl Howell referred to them, that Trump has deployed to evade oversight. “Wow, OK,” Howell said after Trump’s lawyers claimed that the landmark 1974 U.S. v. Nixon case, in which the Supreme Court found that executive privilege could not protect Nixon from a grand jury subpoena for his secret White House tapes, was wrongly decided. In other cases, judges have coaxed absurd stances from Trump’s lawyers, including the argument that it would be unconstitutional to criminally investigate Trump while he occupies the presidency if he murdered someone in broad daylight on Fifth Avenue in Manhattan. The novel and expansive legal theories advanced by Trump would completely reorder the Constitution’s separation of powers to the extreme benefit of the executive branch. They appear to be aimed at an eventual fight before the Supreme Court, where Trump has appointed two of the five justices who make up the conservative majority. Trump believes in a purely transactional version of life. If he scratches your back ― or appoints you to the Supreme Court ― you are expected to return the favor. He calls his judicial appointees “my judges,” and has referred to judges appointed by his predecessor as “Obama judges.” It’s a label Chief Justice John Roberts and other judges have pushed back against. Trump’s supporters, however, have explicitly stated that the fights to appoint Justices Neil Gorsuch and Brett Kavanaugh were fought specifically to install friendly judges on the high court in order to insulate the president from oversight.

ASSOCIATED PRESS In this image provided by the Supreme Court, President Donald Trump poses with Associate Justice Brett Kavanaugh on Nov. 8, 2018, at the Supreme Court in Washington.

“[W]e’ll see whether or not the Kavanaugh fight was worth it,” former House Speaker Newt Gingrich said about a possible Supreme Court case to decide whether Congress can acquire Trump’s tax returns. Kavanaugh is the justice Republicans spent the most political capital to confirm, and the Trump-appointed justice with the longest record on the issues at hand. He has extensive experience working, writing and commenting on presidential power. Depending on how you look at his record, Kavanaugh could provide hope for Trump’s bizarre arguments, or he could spell their doom. There are two positions that Kavanaugh has taken in the past that could be beneficial to Trump ― and have provoked speculation as to why Trump chose him for the Supreme Court in the first place. First, Kavanaugh has argued that the president should not be subject to criminal investigations at all while in office. Kavanaugh argued in a 2009 Minnesota Law Review article that the “indictment and trial of a sitting President” would “cripple the federal government.” Therefore, he continued, “We should not burden a sitting President with civil suits, criminal investigations, or criminal prosecutions.” This appears a beneficial position for Trump, as it relates to his ongoing litigation to prevent Manhattan District Attorney Cyrus Vance from obtaining his tax returns and other financial information, and to a civil lawsuit filed by Summer Zervos, one of more than 50 women who has alleged sexual assault, rape or impropriety against Trump. There is at least one catch. At no point has Kavanaugh suggested that the Constitution provides an exemption from civil or criminal investigation into the president. Instead, he said Congress should pass a law providing such an exemption. This could be viewed as Kavanaugh accepting that originalist or textual arguments for this exemption do not already exist in the Constitution. But he could also find that such an exemption does exist today if the issue were presented before the Supreme Court.

[W]e’ll see whether or not the Kavanaugh fight was worth it. Newt Gingrich, former Speaker of the House and Trump ally

The other major position of Kavanaugh that has been aired on relevant issues is his statement at a 1999 roundtable discussion that the Supreme Court wrongly decided the U.S. v. Nixon case. U.S. v. Nixon is the unanimous 1974 Supreme Court decision that found that there is such a thing as executive privilege protecting some internal White House deliberations, but that the privilege did not apply to materials that could be evidence in a criminal proceeding. The court was determining whether the Nixon White House had to comply with a grand jury subpoena to hand over the White House tapes to special prosecutor Leon Jaworski. “[M]aybe Nixon was wrongly decided; heresy though it is to say so,” Kavanaugh said in 1999. “Nixon took away the power of the president to control information in the executive branch by holding that the courts had power and jurisdiction to order the president to disclose information in response to a subpoena sought by a subordinate executive branch official. That was a huge step with implications to this day that most people do not appreciate sufficiently. ... Maybe the tension of the time led to an erroneous decision.” This hypothetical position dovetails with Kavanaugh’s argument in favor of exempting the president from civil and criminal suits while in office. Overturning Nixon would partially obviate the need for this exemption, as the president could prevent prosecutors from obtaining the evidence necessary to complete their investigations through the assertion of executive privilege. During his confirmation, Kavanaugh was questioned about this past statement about U.S. v. Nixon, and he made sure to assert that he viewed the decision as “one of the greatest moments in American judicial history.” Whether Kavanaugh would ultimately concur with the extreme arguments made by Trump’s lawyers if his challenges reach the Supreme Court is yet to be seen. But his history provides at least some evidence of his congeniality toward them. There’s also bad news for Trump. Kavanaugh has also stated that not only is it totally legitimate for Congress to investigate the president, it’s also preferable.

Bettmann via Getty Images A visitor in the nation's capital reads the headlines in 1974 in front of the Supreme Court telling of the court's ruling ordering President Nixon to surrender 64 White House tape recordings.