Donald Trump and the Republicans like to describe babies born to undocumented immigrants shortly after their arrival as "anchor babies." Per the Fourteenth Amendment, these babies are American citizens. American citizens cannot be deported. In theory, the government could deport the parents and put the babies up for adoption by Americans, but the optics of this aren't very nice. So, effectively, the babies "anchor" the parents in the U.S. and make it (politically) difficult to deport them. This is what Donald Trump wants to change. But how?
Repealing the Fourteenth Amendment is not going to happen because it requires two-thirds of each chamber of Congress to sign on to a new Amendment repealing the Fourteenth, followed by getting three-quarters of the states to ratify it. Trump knows this is too high a bar to clear, and isn't going to go this route. The only Supreme Court ruling on this issue is from 1898 in U.S. v. Wong Kim Ark, in which the Court ruled that Ark was an American citizen because he was born in America. His parents were legal immigrants from China. The Court has never ruled on whether the U.S.-born children of undocumented immigrants are also citizens. Trump wants a ruling on this.
He will try to get his ruling with an XO. Remember that an XO is merely an order to the bureaucracy, not even a law. There are a couple of ways Trump could create a case that could get to the Supreme Court. One is to issue an order to the State Department not to issue any passports to children whose parents cannot prove they are legal residents of the U.S. The parents would no doubt sue and the case would eventually hit the Supreme Court. Who knows how it might rule? The Fourteenth Amendment also says that people who have participated in an insurrection against the United States may not serve in public office, but when a case came up from Colorado, the Court ruled that the Fourteenth Amendment doesn't actually mean anything. It could rule that again.
A second thing Trump could do is order the Social Security Administration not to issue a Social Security number to the children of undocumented immigrants. They would probably sue, as well, providing another potential test case. He could also order the agencies that provide various federal benefits to deny them to the children whose parents were not legal residents. Clearly the people denied passports, SSNs, or benefits would have standing to sue. There would be amicus briefs out the wazoo.
The Supreme Court probably does not want this hot potato, so most likely it would refuse to take any case directly. A challenge would have to first go to a district court, then an appeals court before an appellant could ask for cert. This could take years. If a Democrat is elected in 2028, he or she could make the case moot by simply granting the passport, SSN, or benefit and thus avoiding a ruling. So, Trump could "deliver" on his promise without actually delivering. That is a situation that he has found satisfactory in the past, and may find satisfactory here. (V)