Yesterday evening, Donald Trump launched an attack on the Federalist Society, long viewed as a bastion of conservative thought within the legal community. He also explicitly called out a man named Leonard Leo, someone most people have never heard of. What’s going on? While I have no real answers, I do have some thoughts.

First, here’s Trump’s truth (highlights mine):

I used to belong to the Federalist Society. I joined because it offered affordable Continuing Legal Education seminars (required in California), and I stayed because it was interesting...and because I’d already become disgusted with the American Bar Association and the California Bar Association, both of which were too left for the moderate Democrat I was then.

Although I dropped my membership, I continued to believe for many years that the Federalist Society was a bulwark of originalist rationalism in a sea of leftist judicial activism. I was pleased when Donald Trump looked to the Federalist Society for its nomination recommendations for the Supreme Court. But then...

It turned out that the Federalist Society-recommended justices are primarily textualists, not originalists. This is ironic because the founding purpose behind the Federalist Society was to advance originalism.

Originalism means that you look to what those people who ratified the Constitution or wrote a statute intended when they did so. Thus, under originalism, anyone analyzing the 1964 Civil Rights Act would know that the word “sex” could only refer to biological sex because (a) the people writing the act made that clear and (b) there was no notion in 1964 of any meaning for “sex” other than the biological binary of male and female.

“Textualism,” however, means that you look at the words in a vacuum, which is appropriate when there’s no ambiguity, but a backdoor to leftist-style activism when there is a difference between a modern concept and the concept as it existed when the Constitution was ratified or a law passed.

Under the rubric of “textualism,” Justice Gorsuch was able to say that “sex” means “gender identity,” which is how the left defines the word today. When he wrote that in Bostock v. Clayton County, forcing so-called transgenderism into the Civil Rights Act, he also forced every workplace in America to become a transgender activist. That wasn’t conservative. Ruth Bader Ginsburg was applauding.

Amy Coney Barrett is also a textualist, a polite way of saying activist with a patina of conservativism. Leftists find her delightful.

Brett Kavanaugh is a conservative so soft that he frequently sides with the leftist wing of the Court. (Leftists call this “holding the middle.”)

And of course, there’s Chief Justice John Roberts, an early Federalist Society recommendation. While he occasionally comes through on core conservative issues (i.e., abortion, gay marriage), he’s been a strong foe of the MAGA agenda and, memorably, wrote an insane decision to justify maintaining Obamacare.

These conservative, Federalist Society justices just joined with the leftists on the Court to refuse to hear the case of a Massachusetts student who was silenced for wearing a shirt saying “There are only two genders,” a true statement, because it might hurt the feelings of so-called “transgender” pupils. If there were ever a clear free speech case, this was it, but the Federalist Society’s progeny said no.

No wonder that, at the Supreme Court level, the Federalist Society recommendations have been a bust. We can probably extrapolate that the same is true at the appellate and district court levels.

So, what gives? And who is this Leonard Leo that Trump mentions? Well, if you read a Rob Wasinger essay at American Greatness, you’d have at least one person’s answer to that question. According to Wasinger, Leo is the Federalist Society’s éminence grise, the man responsible for all these (in retrospect) questionable nominations:

The only aspect of the first Trump administration exempt from [the Never-Trump Republicans’] criticism was his handling of judicial appointments, since the choice of nominees to the Supreme Court and to the federal judiciary was largely delegated to billionaire and Federalist Society co-chair Leonard Leo, a stalwart Catholic neocon who has long acted as éminence grise with regard to constitutional law and judicial philosophy among establishment Republicans. In Trump’s first term, Leo used his networks and influence to push through the nominations of Supreme Court Justices Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett, all products of Leo’s Federalist Society. Three other members of the Court, including Chief Justice Roberts, also have Federalist Society pedigrees.

One senses that Leo and the Federalist Society are strongly behind what I would call social conservativism—e.g., no abortion, no transgenderism—but that they are part of a Bush-era bloc that hews to old school Republican policies, which include open borders and unlimited benefits for China in trade matters, and that reflexively hates Trump.

Trump’s attack on the Federalist Society and Leonard Leo is graceless (as his attacks so often are), but it reveals an important schism within conservative judicial philosophy. While leftists are utterly unified (they will always advance all leftist polices and attempt to destroy Trump), the same conservative tensions we see in elections (old-guard Bush-era Republicans versus the MAGA crowd) are playing out with devastating effect in the federal judiciary.

Leonard Leo image cropped from a public domain photo in the White House feed.