Will he win again? Time will tell - he still needs to make it through the primaries, and I think Ron DeSantis is playing better with old school republicans than Trump ever did, but last time Trump did beat Mitt Romney who was pretty widely respected, so its certainly possible. If that happens, I think he is likely to beat Biden. A lot of people voted Biden because he was distinctly "Not Trump", but his victory's have been poorly televised, and his defeats make him look ineffectual and near senile (thanks Murdoch media).

He has already said that if he is elected he will pardon himself. That's never been done before, so would almost certainly go to the supreme court, but since thats Republican controlled I would expect that to get rubber stamped. He's not going to prison if he wins.

Even if elected, the Fourteenth Amendment bans Mr. Trump from legally serving without the approval of 2/3 of Congress, due to his participation in insurrection against the United States. Section 3 says:

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.

I think if he runs then he will lose because he has burned bridges with a lot of Republicans and swing voters. Biden is doing a pretty good job and with Desantis he is pissing off a lot of Republicans also.

As much as I'd like to say, "Oh, there's no way in hell he'd win," I remember saying the same thing in 2016, and here we are. Definitely a Constitutional crisis that would make it up to the Supreme Court, but yeah, we already know how the Conservative majority would decide on it.

Don't get your hopes up, the chances of him going to prison, or bring punished in any way, are basically zero.

Just like every other election, it just depends how many corporations put money behind him.

What if he's sentenced to prison?

There's nothing in the American constitution preventing a convicted felon, or even a prisoner, from being elected president. So it's mostly just up to if he can get the support of Republicans.

Biden has had a couple victories, but they’re difficult to conceptualize into headlines. Things like confirming federal judges and jobless rate reductions. Many people, left and right, see his presidential accomplishments as lukewarm at best. Compare that with the current R headlines, striking down affirmative action, student loan forgiveness, and abortion, expanding the “right to refuse service” based on orientation, and future hearings which will likely further strip protections for LGBT people. These are MASSIVE conservative platform victories that have been campaigned on for decades, literally since the civil rights bill. I don’t think it can be stressed enough just how much red meat is in these few rulings for the conservative base. Couple that with stubborn inflation and negative real wage growth, Dems are looking at a very steep hill next year. Counterpoint, Dems have managed to embolden their younger base to mitigate midterm damage. But morale for this base is likely low given the student loan fiasco, LGBT rights, and a difficult economy.

Trump specifically is looking at two major challenges: legally, he has to avoid sentencing before the election. This will likely be something of a cakewalk for the guy. His federal case is currently being overseen by an openly biased judge who previously ruled in his favor on no basis other than “he’s a former president and should get special treatment”. Even with higher courts excoriating this particular justice, they are not likely to change their rulings this time. State charges are more difficult to dodge, but ultimately he will have fall guys and plea deals to fall back on in most if not all of these cases. A majority of Americans see these cases as political attacks anyway, not unbiased justice, so it’s unlikely these even hurt him in the polls.

The more poignant challenge in my opinion is in winning back independents and moderate Rs. He’s the front runner currently for the nomination, but it’s undeniable his antics wore thin on independents. He ran a divisive campaign and a divisive presidency and, well, it divided people. There’s no walking back some of the horrid opinions or outright lies he espoused. And there’s no hiding how ravenous hard conservatives have become in general for extremism and he and DeSantis are in a race to the bottom on appealing to this base. Time will tell whether independents hold their noses again and vote for him over Biden or another conservative in the primary.

Personally, I don’t see a world where he doesn’t win the primary and face off against Biden in the general. No world where the courts actually pin something to him either. If you don’t want to see another Trump presidency, swing state independents are gonna be your best shot.

Everyone keeps talking about the fact that he may pardon himself. That is very likely true but let's not forget the fact that anyone else who is elected can pardon him without raising the same constitutional crisis. He could also be elected, resign and be pardoned by his former VP (I find it doubtful he would go this route). None of these will affect charges on the state level, however.

Trump cannot possibly be sentenced to prison. He can and does deserve it, but it's utterly impossible. Might as well wonder how high could pigs fly if pigs could fly.

He'll be dead long before he's sentenced to prison. If he doesn't win, his usefulness is over with and he knows too much for the people that run the show to let him keep breathing.