Judge Brett Kavanaugh (CUA Law School via YouTube)

There’s a difference between a home run and a grand slam.

Since the moment Justice Kennedy stepped down, an intense, mostly friendly battle has been waged in public and in private over Judge Brett Kavanaugh. Some of the claims are silly. He’s no “squish.” He’s a brilliant jurist who’s written some of the best and most influential appellate-court decisions in the United States. And whisper campaigns that call him the “low-energy Jeb Bush pick” or claim that he’d somehow be a “compromise” nominee are simply wrong.


Let’s put it this way: If Kavanaugh is some sort of deep-cover David Souter, he’s done a remarkably good job of hiding it, building a mountain of stellar originalist jurisprudence. Ed Whelan has been doing yeoman’s work over on National Review’s Bench Memos blog, righteously defending Kavanaugh’s record on religious liberty, the Second Amendment, free speech, immigration, and the administrative state. And Ed isn’t alone. Pieces from former Kavanaugh law clerks at The Federalist and at NRO have ably defended him from attacks and highlighted the best parts of his jurisprudence.

In evaluating Kavanaugh, there’s only one reasonable conclusion to draw: He’d be an excellent Supreme Court justice, and he would make the Court substantially more originalist and rigorous.


But saying that he’s an excellent pick is not the same thing as saying that he’s the best available pick. There’s a difference between a home run and a grand slam. The question — given this unique moment in which the Trump administration is listening to the best conservative legal minds, Republicans control the Senate, and the filibuster is a thing of the past — is whether Kavanaugh represents the grand slam.

I have my concerns, and those concerns are rooted in two cases that have been oft-misrepresented in the debate over Kavanaugh but are consequential nonetheless. The first is Seven-Sky v. Holder (better known as Kavanaugh’s Obamacare case). The second is Priests for Life v. HHS (an Obamacare contraception-mandate case.) In both cases, his reasoning is sharp and his legal decisions are defensible. In both cases, however, I believe he made important errors.


Let’s deal with Seven-Sky first. Judge Kavanaugh wrote an opinion dissenting from the majority’s determination that it had jurisdiction to hear the plaintiff’s challenge to Obamacare. He did not reach an opinion on the underlying merits of the case, which is to say, on the question of whether Obamacare was constitutional.

The legal details matter here. Kavanaugh held that the Anti-Injunction Act applied to bar the plaintiffs’ suit. As he explained, “Under the Anti-Injunction Act, a taxpayer seeking to challenge a tax law must first pay the disputed tax and then bring a refund suit, at which time the courts will consider the taxpayer’s legal arguments. Or a taxpayer may raise legal arguments in defending against an IRS enforcement action. But a taxpayer may not bring a pre-enforcement suit.” The challenge to Obamacare was a “pre-enforcement suit” and was thus barred:

The Anti-Injunction Act applies here because plaintiffs’ pre-enforcement suit, if successful, would prevent the IRS from assessing or collecting tax penalties from citizens who do not have health insurance. To be sure, the Affordable Care Act labels its exaction for failure to have health insurance as a tax “penalty” and not as a “tax.” But the Anti-Injunction Act still applies. That’s because the Affordable Care Act requires that the tax penalty for failure to maintain health insurance “be assessed and collected in the same manner as an assessable penalty under subchapter B of chapter 68” of the Tax Code. 26 U.S.C. § 5000A(g)(1). And penalties under subchapter B of chapter 68 in turn must “be assessed and collected in the same manner as taxes.” 26 U.S.C. § 6671(a) (emphasis added). It follows from those two provisions, taken together, that these Affordable Care Act penalties must be assessed and collected “in the same manner as taxes.”

This is a defensible reading of the relevant Obamacare provisions. Indeed, while the majority in the most consequential Obamacare case to reach SCOTUS, NFIB v. Sebelius et al., did not apply the Anti-Injunction Act, it did hold that the penalty was a tax. That was a reasonable response to the statutory language, but it was wrong. The Obamacare penalty was a penalty, not a tax. Justices Scalia, Alito, Thomas, and Kennedy made the better argument, in their stinging dissent:

In answering that question we must, if “fairly possible,” Crowell v. Benson, 285 U. S. 22, 62 (1932), construe the provision to be a tax rather than a mandate-with-penalty, since that would render it constitutional rather than unconstitutional (ut res magis valeat quam pereat). But we cannot rewrite the statute to be what it is not. “‘“[A]lthough this Court will often strain to construe legislation so as to save it against constitutional attack, it must not and will not carry this to the point of perverting the purpose of a statute . . .” or judicially rewriting it.’” Commodity Futures Trading Comm’n v. Schor, 478 U. S. 833, 841 (1986) (quoting Aptheker v. Secretary of State, 378 U. S. 500, 515 (1964), in turn quoting Scales v. United States, 367 U. S. 203, 211 (1961)). In this case, there is simply no way, “without doing violence to the fair meaning of the words used,” Grenada County Supervisors v. Brogden, 112 U. S. 261, 269 (1884), to escape what Congress enacted: a mandate that individuals maintain minimum essential coverage, enforced by a penalty. Our cases establish a clear line between a tax and a penalty: “‘[A] tax is an enforced contribution to provide for the support of government; a penalty . . . is an exaction imposed by statute as punishment for an unlawful act.’” United States v. Reorganized CF&I Fabricators of Utah, Inc., 518 U. S. 213, 224 (1996) (quoting United States v. La Franca, 282 U. S. 568, 572 (1931)). In a few cases, this Court has held that a “tax” imposed upon private conduct was so onerous as to be in effect a penalty. But we have never held — never — that a penalty imposed for violation of the law was so trivial as to be in effect a tax. We have never held that any exaction imposed for violation of the law is an exercise of Congress’ taxing power — even when the statute calls it a tax, much less when (as here) the statute repeatedly calls it a penalty. When an act “adopt[s] the criteria of wrongdoing” and then imposes a monetary penalty as the “principal consequence on those who transgress its standard,” it creates a regulatory penalty, not a tax. Child Labor Tax Case, 259 U. S. 20, 38 (1922).

While it is most certainly true that Judge Kavanaugh did not rule on the underlying constitutionality of what he called the “tax penalty” (and he offered a ringing critique of the government’s Commerce Clause justifications for the individual mandate), he got the fundamental question (tax or penalty?) wrong, and Justices Kennedy, Scalia, Alito, and Thomas got it right. That’s a cause for some concern.


There is also cause for concern in his reasoning in Priests for Life. His dissent reached the right result, but his reasoning was dangerously flawed in one key respect: He excessively inflated the government’s interest in facilitating access to contraceptives.

As he explained in his opinion, he had to consider three questions: Did the contraception mandate “substantially burden” Priests for Life’s “exercise of religion”? If so, were the Obama administration’s regulations justified by a “compelling” governmental interest? And, finally, if there was a compelling governmental interest, did those regulations represent the “least restrictive means” of advancing that interest? Here were Judge Kavanaugh’s conclusions:

First, under Hobby Lobby, the regulations substantially burden the religious organizations’ exercise of religion because the regulations require the organizations to take an action contrary to their sincere religious beliefs (submitting the form) or else pay significant monetary penalties. Second, that said, Hobby Lobby strongly suggests that the Government has a compelling interest in facilitating access to contraception for the employees of these religious organizations. Third, this case therefore comes down to the least restrictive means question.

Judge Kavanaugh held that the Obama administration had not chosen the least restrictive means to advance its allegedly “compelling” interest, and therefore would have ruled for Priests for Life.

The problem is with his second conclusion. Here’s how he explained it later in his opinion:

Justice Kennedy strongly suggested in his Hobby Lobby concurring opinion — which appears to be controlling de facto if not also de jure on this particular issue — that the Government generally has a compelling interest in facilitating access to contraception for women employees.

Is that correct? And if his summary of Justice Kennedy’s concurrence is correct, then was Judge Kavanaugh actually bound to follow it?

To understand why I believe Judge Kavanaugh’s reasoning is erroneous, it’s important to give a bit of background on Hobby Lobby. The case was a 5–4 decision, with Justice Kennedy filing a separate concurring opinion. Justice Alito’s majority opinion simply assumed (without holding) that the government’s interest in providing the “challenged contraceptive methods” was compelling within the meaning of the Religious Freedom Restoration Act.

But before making that assumption, Justice Alito wrote these vitally important words: RFRA, he said, “requires the Government to demonstrate that the compelling interest test is satisfied through application of the challenged law ‘to the person’ — the particular claimant whose sincere exercise of religion is being substantially burdened.”

To put it plainly, according to Alito’s reasoning, under RFRA the government would have to establish a compelling governmental interest in facilitating access to contraceptives not just for women generally but as applied to the specific plaintiffs.

Justice Kennedy, in his concurrence, says this:

It is important to confirm that a premise of the Court’s opinion is its assumption that the HHS regulation here at issue furthers a legitimate and compelling interest in the health of female employees.

It’s important to note that an “assumption” is not a holding. Moreover, this “assumption” doesn’t fully grapple with Alito’s statement that the compelling-interest analysis applies to the “particular claimant whose sincere exercise of religion is being substantially burdened” — in this case, Priests for Life.

Yet Kavanaugh glided past Alito’s language and applied the Kennedy “assumption” to the “employees of these religious organizations.” This application was not compelled by Kennedy’s concurrence, and it ultimately fails as a matter of logic and reason when applied to Priests for Life.

While the government may well deem that contraceptives provide many general benefits (and Kavanaugh outlines those benefits in his opinion), that is not the same thing as holding that those general benefits are sufficiently compelling as applied to the employees of a small religious nonprofit. After all, no one is forced to work for Priests for Life, its employees undertake their duties as part of a religious mission, and it would even be within the rights of Priests for Life to bar its employees from using contraceptives.


Where is the compelling governmental interest in facilitating access to drugs that a religious employer may prohibit as a condition of employment?

Again, I outline these concerns not because I believe Judge Kavanaugh is a “squish” or because I believe his opinions were indefensible. I simply think his reasoning was flawed — and flawed in two critically important, high-profile cases. When deciding between excellent candidates (and Trump’s short list includes only excellent candidates), it’s worth considering — as I said above — whether a nominee is a grand slam or “only” a home run. I’m simply not sure that Kavanaugh is the grand slam.