Updated March 27, 2023 at 6:28 PM ET

Look at the the Supreme Court's history, and you will see a lot of cases in which odious defendants bring tough First Amendment questions. Monday's case was one of those.

The issue was whether a federal law that makes it a crime to encourage or induce illegal immigration transforms some speech protected by the Constitution into a crime.

The defendant in this case is Helaman Hansen, who conned 471 noncitizens into believing that they could obtain U.S. citizenship through adult adoption. By enrolling these noncitizens in this nonexistent program, Hansen defrauded these people of more than $1.8 million. In 2017, a jury convicted him on 15 counts of mail and wire fraud, for which he was sentenced to 20 years in prison. But it also found him guilty of two counts of encouraging or inducing these noncitizens to remain in the United States, and it is those two counts that were the focus of Monday's argument.

The Ninth Circuit Court of Appeals ruled in favor of Hansen, declaring that the federal law making it a crime to induce unlawful immigration sweeps up a substantial amount of speech that is protected by the First Amendment. The government appealed, and on Monday Deputy Solicitor General Brian Fletcher sought to thread a tiny legal needle: With one hand he made strategic concessions, while with the other he sought to uphold the statute. He conceded that the jury had not been properly instructed on the defendant's intent, and that the statute could be read too broadly. But, noting that the law has been applied for 70 years, he argued that if it is narrowly construed, it does not run afoul of the First Amendment.

"Prohibitions on soliciting or facilitating both criminal and civil violations have long been common and have never been thought to raise a First Amendment problem," Fletcher said. "The First Amendment does not protect speech that is intended to induce or commence specific illegal activities."

The justices, however, had a lot of questions.

"What do you say to the charitable organizations that say, even under your narrowing construction, there's still going to be a chill or a threat of prosecution for them for providing food or shelter and aid," asked Justice Brett Kavanaugh.

Justice Sonia Sotomayor followed up, saying, "We do know that the Customs Department made a list of all the people, religious entities, the lawyers and others who were providing services to immigrants at the border and was saying they were going to rely on the statute to prosecute them."

Justice Elena Kagan added, "What happens to all the cases where it could be a lawyer, it could be a doctor, it could be a neighbor, it could be a friend, it could be a teacher and could be anybody, says to a noncitizen, 'I really think you should stay.' What happens to that world of cases?"

Responding to a question from Sotomayor about a grandmother who worries that her immigration status might be a burden on her children but stays in the U.S. at their urging, Fletcher acknowledged that when family members urge someone to stay, that is the hardest case. He said there is no way to deal with all the variables that could come up, prompting Sotomayor to ask, "Why should we uphold a statute that criminalizes words . . . that's what we're doing with this statute. It's a first of [its] kind."

ACLU lawyer Esha Bhandari picked up that thread, arguing on behalf of the defendant.

Unless the court clips the wings of this statute, she said, "Congress and the states will be free . . . to criminalize speech soliciting violations of the vast range of administrative and regulatory laws that govern us today, from mask and vaccine mandates to parking ordinances."

But she too faced some tough hypotheticals. "What about someone who encourages a person who is intellectually disabled to commit suicide?" asked Justice Samuel Alito.

Bhandari replied that the government has an interest in protecting the vulnerable, and if a statute were narrowly drawn, it could survive.

Justice Neil Gorsuch asked Bhandari how her client's rights are being violated, noting that under just about any standard of intent, he would be convicted.

Bhandari acknowledged that her client had defrauded many people and will go to jail for 20 years. But, she said, the challenge here is to the statute as a whole and how it could inhibit speech about almost anything.

The government, with all its concessions on Monday, tried its best to persuade the court that a decision narrowly construing the statute would allow it to remain on the books. Whether it won the day remains to be seen.

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