One of Donald Trump's first executive orders is also the one that will generate the fastest lawsuit: his attempt to end birthright citizenship. It's a case that's ultimately destined for the Supreme Court because, win or lose, everyone will ensure it gets appealed to that level. I expect Donald Trump to lose. The only way to achieve what Trump wants is by amending the U.S. Constitution. An executive order doesn't cut it.

The first sentence in the 14th Amendment, passed in the wake of the Civil War, is at issue. One of the first tasks of Congress was to establish that newly freed slaves were actually citizens of the United States. Before the war, in 1957, the Supreme Court ruled in the infamous Dred Scott case that blacks were not citizens as defined under the United States Constitution and did not enjoy the same legal protections granted to U.S. citizens.

The answer to reversing the Dred Scott decision was the 14th Amendment. The first sentence of the first clause is where birthright citizenship gets its claim. The Amendment states: "All persons born or naturalized in the United States, and subject to the jurisdiction thereof, are citizens of the United States and of the state wherein they reside."

For our purposes, you can shorten that to, "All persons born ... in the United States, and subject to the jurisdiction thereof, are citizens of the United States." Under this clause, to be a natural-born citizen, you need to be two things: 1) born on United States soil and 2) subject to its jurisdiction.

In the post-Civil War period, this swept every slave into full citizenship rights and ended the tyranny of the Dred Scott decision. In the modern context, does this clause apply to a baby born on U.S. soil to illegal immigrants? You'll sometimes hear this referred to as having an anchor baby.

For all of U.S. history, the answer to this question is: yes, that baby is a full U.S. citizen. The Trump executive order disputes this by trying to redefine what the clause "subject to the jurisdiction thereof" means.

In 2007, Judge James Ho explained what this clause meant:

When a person is "subject to the jurisdiction" of a court of law, that person is required to obey the orders of that court. The meaning of the phrase is simple: One is "subject to the jurisdiction" of another whenever one is obliged to obey the laws of another. The test is obedience, not allegiance.

The "jurisdiction" requirement excludes only those who are not required to obey U.S. law. This concept, like much of early U.S. law, derives from English common law. Under common law, foreign diplomats and enemy soldiers are not legally obliged to obey our law, and thus their offspring are not entitled to citizenship at birth. The 14th Amendment merely codified this common law doctrine.

A typical example is a foreign diplomat. If such a person lives abroad with his family and has a baby, that baby is still a citizen of the country the diplomat is from, not the United States.

Judge Ho noted, "Members of the 39th Congress debated the wisdom of guaranteeing birthright citizenship — but no one disputed the Amendment's meaning. Opponents conceded — indeed, warned — that it would grant citizenship to the children of those who "owe [the U.S.] no allegiance." Amendment supporters agreed that only members of Indian tribes, ambassadors, foreign ministers and others not "subject to our laws" would fall outside the Amendment's reach."

In short, Congress knew at the time of ratification that they were opening the door to allowing anyone born on U.S. soil to become a citizen. They decided to live with the consequences of that decision. Obviously, the United States was not the location of immigration that it would become in later decades after the war. But the implications of the Amendment were clear.

And that brings the broad problem with Donald Trump's executive order: I'm not aware of any legal scholarship, historical source, or textual argument related to the 14th Amendment that gets any court to where he wants the conclusion to be. There are novel attempts to claim otherwise, but no court in the United States has taken these arguments seriously.

That brings us to the Supreme Court. When this eventually makes it to the Supreme Court, I'd expect the Supreme Court to reject the novel arguments unanimously. There's simply no textualist, originalist, or historical argument that changes reality or practice.

If Congress and the states want to change the rules around birthright citizenship, they can amend the constitution. That's always in play, and there have been no serious attempts to do that, either. That means Donald Trump's first major legal battle is also doomed from the start.