Unless Trump dies naturally before the end of his term (I.e., January 2029), I would expect Trump to resign a day or so before the end of his term and have then President Vance give him a blanket pardon for any and all crimes.

While the pardon will really only apply to Federal crimes, Trump and his lawyers would use the confusion to delay any jail time until he does pass away.

The two things aren’t related, but for a mildly tangential link: if Donald Trump is no longer President/Dictator/Authoritarian-in-Chief, then he loses the protections of the Presidency, and once again becomes subject to the law.

The you ask whether Trump goes to jail if a Democrat wins in 2028 rather goes to show how poorly-understood the US political system is. The President doesn’t govern the judiciary, and has no power to have a person convicted and jailed under the law. They can’t even “order” someone’s arrest: whilst the DOJ can, they have to have sufficient grounds to do so (except, ironically, under the Trump Administration), and must ultimately justify their actions before the courts. For a person to end up in prison over the long term, they must face trial and be convicted by an impartial jury – something the President has no authority over.

Personally, I doubt Trump will ever face so much as a day in jail: his actions of late make it clear that he’s intent on stacking the Federal Government with sycophants and loyalists, and equally that he plans to weed out anyone loyal to the United States out of any position of authority. Judges who dare to rule against his whims are threatened with impeachment. Federal employees who do not bow to his whims are pushed out the door.

Reporters who don’t say “Gulf of America” instead of “Gulf of Mexico” end up banned from the White House Press Corps. It’s fair to say that Trump isn’t likely to see a government run for the people, by the people when 2028 rolls around – he will want one subservient to his will, and he won’t relinquish power voluntarily.

Should he ever face charges – which I doubt, given the way he managed to tie up his cases within the courts long enough to once again obtain legal immunity from prosecution – he may well end up having to face a judge who he placed into office, and who will protect him above their obligations to the country. It’s worth noting, by the by, that Special Counsel Jack Smith had his cases dismissed without prejudice, precisely so they could be resurrected if/when Trump leaves office again…but whether those would ever get any further is anyone’s guess. I’m quite certain that one of Trump’s primary goals of his second term is to make sure any evidence against him disappears.

In truth, though, I’m sceptical of the idea that the United States will survive Donald Trump. He’s made his authoritarian intentions clear, and his brief tenure in office since re-election has been fraught with government disassembly, a shocking number of violations of Separation of Powers (to the point that Trump is gleefully ignoring Congress, and even violating court orders), and we’re at the point where his thugs are actively kidnapping people off the streets and holding them in detention without due process. Face it: whatever we thought the United States was before is clearly dead. All we’re waiting to see is what happens to the people left to mourn it.

Further, Trump himself may not survive long enough to face sentencing even if he were to be indicted and brought to trial. The past few years showcased the reality that he can use legal loopholes and procedure to tie up his cases indefinitely, and charges wouldn’t be brought until 2029 at the earlier (if ever), so there’d be a fair chance that he’d kicked the bucket before anything actually went to trial.

Plus, let’s be real here: are there likely to even be elections in 2028? Trump’s already got the Republican Party actively advocating a third term in office (judging by the rhetoric we saw at the recent CPAC convention), and his present approach to governance (and, indeed, the US Constitution) suggests that he doesn’t think the rules apply to him, and he can do as he pleases. Again, I don’t see him going quietly at this stage.

So…no, I don’t think Trump will ever end up in jail. To be honest, I’m starting to think that the best case scenario is that Trump will be removed from office by force and killed in the process. That’s likely to have a much lower body count than any of the alternatives that seem to be in front of us now. And that worries the hell out of me.

It depends on how long he lives and how long he manages to delay prosecutions for.

My understanding is that there are still prosecutions pending for the interference with state election processes in Georgia. whilst the prosecution for the National Security violations and cover-up therof at Mar-a-lago could be re-opened.

It does not need a Democrat to win in 2028 for these prosecutions to be dusted off and trials to start, any sane, responsible Republican President would not interfere with the independence of the DoJ or State prosecution service.

Of course, the above assumes that the USA is a country that follows the rule of law and has due process for the investigation and prosecution of crimes. Sadly, that USA died in January 2025 after a long drawn-out illness.