Could the 14th amendment, section 3, keep Trump from holding office for a second term?

Question

It seems widely agreed upon that even if a President breaks a law, he can only be removed from office through the impeachment process.

However, could an incumbent president who wins a second term be kept from being seated due to the 14th amendment (section 3)? It reads (emphasis mine):

Section. 3. No person shall be a Senator or Representative in Congress, or elector of President and Vice President, or hold any office, civil or military, under the United States, or under any State, who, having previously taken an oath, as a member of Congress, or as an officer of the United States, or as a member of any State legislature, or as an executive or judicial officer of any State, to support the Constitution of the United States, shall have engaged in insurrection or rebellion against the same, or given aid or comfort to the enemies thereof. But Congress may by a vote of two-thirds of each House, remove such disability.

Apologies because this is a multi-part, not-straightforward question:

1. Does the above bolded part correspond to breaking any specific laws? That is, how would one show that a person engaged in insurrection or rebellion, or given comfort to enemies?
2. If this could be demonstrated by finding someone guilty of a particular law, in theory couldn't someone bring federal charges against Trump for doing so? (assuming one of his many bad faith acts like cooperating with Russian election interference, or tweeting classified information appeared to be breaking said law).
3. Couldn't this happen even if a Republican controlled senate decided not to remove him from office after being impeached? That is, even if it wouldn't cause him to be removed from office, couldn't he, separate from impeachment, be convicted of a crime while still holding office?
4. If he was found convicted of a crime which fit the above bolded passage (and didn't engage in some shenanigans like pardoning himself), who would keep him from taking office? (i.e. enforce the law).

I apologize if I'm grossly misinterpreting things here. My background knowledge is just from Wikipedia and constitution.findlaw.com, and I couldn't find any articles dealing with Trump and the 14th amendment, section 3 (all results were about him trying to unilaterally change citizenship laws, so for a different section).

Answer 1

I apologize if I'm grossly misinterpreting things here.

You are grossly misinterpreting things here. Your mistakes aren't terribly uncommon, but you are completely and totally wrong in what you are suggesting.

Does the above bolded part correspond to breaking any specific laws? That is, how would one show that a person engaged in insurrection or rebellion, or given comfort to enemies?

The language intentionally mimics the only crime defined in the U.S. Constitution, which is treason, defined in U.S. Constitution, Article III.

If this could be demonstrated by finding someone guilty of a particular law, in theory couldn't someone bring federal charges against Trump for doing so? (assuming one of his many bad faith acts like cooperating with Russian election interference, or tweeting classified information appeared to be breaking said law).

None of the things you imagine could constitute treason. 'Enemy" is a term of art that means a country that the United States is actually at war with, militarily, by providing aid and comfort to the other side that aides them in waging war with the U.S.

Cooperating with Russian election interference isn't treason. Inaction isn't treason. The President probably has an absolute legal right to disclose information that is classified for national security purposes. The President is immune from civil and criminal liability for his official acts while he is President.

If the President, from his private funds, and not as part of his officially duties, personally paid Taliban soldiers bounties to shoot and kill American soldiers, that might be treason (since the U.S. is at war, within the meaning of the treason statute, with the Taliban). Cooperating with Russia, despite the fact that it has done so is not treason.

Even then, federal prosecutors would not press these federal charges against the President while the President was in office. And, the President would be immune, in all probability, to state treason charges for conduct while in office. So the President would have to be prosecuted after leaving office. On the other hand, Section 3 of the 14th Amendment does not require a criminal conviction to be effective.

The intent of Section 3 of the 14th Amendment was to deny civil rights in the post-Civil War governments of the United States by Confederate officials and military officers. In practice, Congress used the authority it was granted to remove political disabilities from all but about 500 of the hundreds of thousands or millions of people eligible for this treatment under the 14th Amendment.

Couldn't this happen even if a Republican controlled senate decided not to remove him from office after being impeached? That is, even if it wouldn't cause him to be removed from office, couldn't he, separate from impeachment, be convicted of a crime while still holding office?

The federal government prosecutes treason. Ultimately, the President is the one who decides whom the federal government prosecutes. So, the President as a practical matter could not be convicted of treason while still holding office, even if he committed acts which actually constitute treason, unlike anything could be plausibly alleged in this case.

If he was found convicted of a crime which fit the above bolded passage (and didn't engage in some shenanigans like pardoning himself), who would keep him from taking office? (i.e. enforce the law).

A future President can pardon the crime of treason by a former President. Ford pardoned Nixon of crimes that Nixon committed, and many Presidents have pardoned treason convictions at times close to the adoption of the U.S. Constitution and to the adoption of the 14th Amendment. But this just can't come up in this case. You'd need a treason to have been committed before someone was elected.