By Andy Grewal’s own accounting, the course of his career has often been marked by luck — “dumb luck,” in his own words.
In fact, the Iowa University College of Law professor, known for his witty Twitter account and often contrarian stances on noteworthy topics like congressional Democrats’ quest for President Trump’s tax returns, didn’t even initially set out to be a lawyer, much less a tax law academic. Grewal wanted to be a journalist.
He initially applied to Northwestern University’s Medill School of Journalism, but was rejected. “I was so heartbroken that I just gave up journalism entirely,” he told Tax Notes.
Instead, Grewal took up law. But after his first year of law school, he decided he didn’t like any of those first-year courses all that much, so he just decided — without having taken any tax classes — that he would specialize in whatever area seemed completely different from everything else.
“Somehow it worked out,” he said.
Grewal’s additional interest in the then-nascent field of administrative law turned out to be prescient. While earning his LLM in tax at Georgetown University Law Center, from which he graduated in 2006, he took classes on administrative law and statutory interpretation, and it was during that time that he said the two subjects were fused together in his mind.
At the time, few people in the tax world were giving much thought to matters of administrative law, like whether notice and comment is required for the issuance of regulations.
Then in 2010, the Supreme Court took up Mayo Foundation v. United States, 562 U.S. 44 (2011), ultimately deciding that administrative law principles generally apply to tax regulations. “Then it kind of exploded, but I was already there,” Grewal said.
“I guess I kind of lucked into it,” he added.
But Grewal’s lucky streak was only getting started.
Having long enjoyed writing, Grewal wrote a 40-page paper while working on his LLM that was eventually published. “When I did that, I thought, ‘Wow, this is something I want to do permanently,’” he said, adding that it put the idea of teaching in his mind.
For the next few years, he worked in the private sector in Washington — first at Mayer Brown, and then at Skadden, Arps, Slate, Meagher & Flom LLP — but he continued to write, even having a few articles published in Tax Notes.
In early 2009, Grewal decided to apply for a teaching position at Arizona State University. At the same time, in the wake of the financial crisis, Skadden was offering to pay its associates to “disappear for a year.”
“I got really lucky,” Grewal said. “I got paid to leave when I was planning to leave anyway.”
In another stroke of good fortune, Grewal’s early scholarly interest in the obscure issue of congressional tax oversight authority took on real salience once Trump was elected in 2016.
A Vox article showed that almost a dozen legal experts were nearly unanimous in affirming that the House Ways and Means Committee’s legal authority to subpoena Trump’s tax returns was absolute and justified. One respondent even said that anyone who argues otherwise “is either a partisan hack or contemptuous of the rule of law.”
But then there was Andy.
“If you’re in a tax bubble and you look at the statute . . . this seems to be an easy case. The statute just says, ‘Turn it over,’ and that’s that,” Grewal said. But in his view, there are larger overarching constitutional principles at play.
As it happened, Grewal had already closely studied when Congress can access tax return information well before almost anyone else had given it much thought. He said it was still a sleepy topic when he wrote “The Congressional Revenue Service” in 2014, which argued that Congress needs to have a legitimate legislative purpose to obtain private taxpayer information.
Then, once Trump was elected and people began talking about Congress subpoenaing the president’s tax returns, Grewal said he was “already primed to go” because of his prior research, so he wrote a few blog posts on the topic in 2017. But it wasn’t until 2018, when the House flipped to Democratic control, that the question began to take on even more salience and formal inquiries into Trump’s tax returns began.
In that context, Grewal wrote another article in 2019, “The President’s Tax Returns,” which contended that in light of constitutional principles regarding Congress’s investigatory authority, congressional committees lack the automatic authority of section 6103(f) to demand a president’s tax returns absent a legitimate legislative purpose that many seem to suppose.
“There’s nothing about being the president in and of itself that would make congressional requests legitimate,” Grewal said. His 2019 article didn’t reach a specific conclusion on Trump’s tax returns. But he added that he was delighted to see the Supreme Court handle analogous issues similarly in Trump v. Mazars & Deutsche Bank, No. 19-715, No. 19-760 (S. Ct. 2020).
That case didn’t specifically address Trump’s tax returns, but it was similar in that it initially seemed straightforward that the House Oversight and Reform and Foreign Affairs committees could subpoena Trump’s financial information. “But the Court said, ‘Hold on, you need a legitimate legislative purpose . . . and you need to do more work to establish that a request is legitimate,’” Grewal explained, adding that it wasn’t even an ideologically split decision.
Grewal has some advice for congressional Democrats in another case by the House Ways and Means Committee, which is subpoenaing Trump’s returns to provide oversight of how the IRS audits presidents.
Democrats should follow the Republicans’ example at the start of the so-called Tea Party scandal regarding the IRS’s handling of conservative groups’ applications for tax-exempt status. That could involve establishing a strong basis for requesting Trump’s returns by asking the Treasury Inspector General for Tax Administration to investigate any improprieties in the way the returns have been handled by the IRS. If TIGTA identified any irregularities, the Democrats’ request would have much more legitimacy, he said.
University of Chicago Law School professor Daniel Hemel — who acknowledged that he disagrees with Grewal on so many topics that he can’t decide which issue he disagrees with him most on — said that he actually agrees that a legitimate legislative purpose is needed to obtain Trump’s tax returns, but he believes Congress has that justification already.
A big part of that disagreement, and many others he has with Grewal, hinges on a fundamental disagreement over how big of a threat the Trump administration is to American democracy and constitutional order, Hemel continued.
“My view is, these are not normal times and that we have some obligation in scholarship and working to address the Trump threat. And Andy has a different intuition on that,” Hemel said.
As he did with Congress and tax returns, Grewal got a head start in the field of tax and administrative law.
His early scholarship in administrative law made an impression on the “champion of anti-tax-exceptionalism” herself, University of Minnesota Law School professor Kristin Hickman. “I like scholarship that is interesting and makes a new point, but also that has some real-world connection to it,” Hickman told Tax Notes.
According to Hickman, Grewal’s 2006 article, “Substance Over Form? Phantom Regulations and the Internal Revenue Code,” which critiqued the practice of deferring to judicial opinion in the absence of Treasury regulations, was “really novel” and was later cited by the Tax Court.
Hickman recalled she was first introduced to Grewal by a former colleague at Skadden, where she had also worked for a time, in part because of his interest in tax and administrative law. It was that interest in a field that few people paid much attention to at the time that led Hickman to ask Grewal to moderate an event panel in her place.
In the years since Mayo, however, scholarship in tax administrative law has grown exponentially, and Grewal has contributed greatly to that development, Hickman said. Grewal has written several academic articles in that area, where he often falls on the anti-tax-exceptionalist side, as well as offered comments on others’ work.
Grewal acknowledged the fortunate timing of his own interest in tax and administrative law coinciding closely with the subsequent Mayo case. “That, I guess, was just dumb luck. If I had taken up the same interest in 1990 or something like that, that area would probably have continued to toil in obscurity, but now it’s grown quite a bit,” he said.
Hickman said that despite Grewal’s pugilistic online reputation, she wouldn’t define his academic role as a chronic contrarian. His scholarship covers a wide variety of topics and he often simply brings a unique or minority view, she remarked.
For example, while Grewal generally falls into the anti-tax-exceptionalist camp, his position is nuanced, Hickman said. She highlighted his 2016 article on whether the rule of lenity should apply to tax statutes, where if a statute is ambiguous and has competing interpretations, the interpretation that favors the defendant should be adopted. However, in that article, Grewal argued against applying the rule of lenity to tax.
“It was an interesting contribution to an ongoing conversation,” Hickman said.
Everybody Loves Andy
Grewal says he doesn’t mind his contrarian reputation. “It makes academia more fun,” he said. “If you’re an academic, the most boring thing in the world is everyone in the world telling you you’re right.”
That habit of taking nuanced minority positions on issues has endeared Grewal to at least some of his colleagues.
“Andy is someone who has the gift of being able to disagree without being disagreeable,” Hemel said. “Academia can often become an echo chamber, but in tax and administrative law at least, Andy has made it his mission to ensure that it’s not.”
Hemel recalled that the ancient Jewish Sanhedrin court had a rule that to sentence someone to death, the verdict could not be unanimous. It was considered suspicious if everyone uniformly agreed, because unless someone voices the best counterargument, “then you can never really be confident in your own view,” he explained.
“The stakes are generally lower than death here,” Hemel continued. “[But] I think Andy makes it his mission to offer the best counterargument on a wide range of issues. And that’s extraordinarily valuable.”
Hickman also found Grewal’s unique positions appealing. “He’s a bit irreverent, as you’d know if you’ve read his Twitter feed, but he’s also very charming and a lot of fun. . . . If you’ve gotta get stuck next to somebody at a three-hour dinner, Andy would be at the top of the list of people I’d want to get stuck next to,” she said.
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