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Whether he's right or wrong, I think Trump sincerely wants to be thrown in jail right now, as long as it's not for the crimes he committed. He wants to be thrown in jail for something (relatively speaking) petty that he can use to paint himself as a martyr that is being politically persecuted. Because he knows that going down this path, one or more of the following things will happen:
He starts daring more judges to hold him in contempt. Judges, already going out of their way to bend over backwards for Trump, back down out of either fear of general violence or out of fear for their own or their family's safety. Once he shows their unwillingness to follow through on their threats, he can ignore further gag orders pretty much with impunity.
A judge actually does hold him in contempt of court. Let's say even if it's overnight just to send a message that Trump's behavior won't be tolerated. Then violence breaks out as it gets the MAGA crazies all sorts of riled up. Good luck holding Trump accountable for anything ever again. You think people are gunshy now, imagine what will happen if there's a mass shooting incident in response to Trump being arrested. Or if someone who was targetted by Trump got killed by one of his followers.
The MAGA base will become energized and rally around Trump, sending him soaring in the polls (Keep in mind, every indictment so far has actually seen his polling numbers rise). The MAGA crazies (Jordan, MTG, Gaetz, etc.) are going to try to run interference on his behalf. Downticket Republicans are essentially told by their base (which in many areas is still large enough to dictate political careers) to vote in lockstep with Trump or be primaried/voted out themselves. This leads to the very real possibility that not only does this help propel Trump back to the white house, it may even lead to more crazies getting elected to Congress to help Trump on the Trump Revenge Tour.
It will keep the attention on Trump 24/7. A former President of the US being put in jail for any reason would be the biggest story of the year, and it wouldn't even be close. And there is not a single second that would go by without mainstream media covering it parked right in front of the jail. This means 24/7 coverage about Trump being in jail. Not policies. Not Biden. Not Ukraine. Not Gaza. Trump. Trump will get free publicity from the entire mainstream media industry as all they tell people is that "Trump is in jail!" all day, every day. They will be talking about nothing but Trump. And that's exactly what he wants. As long as they're talking about him, that's all he wants. Good or bad, doesn't matter. If they're talking about him being in jail, they're not talking about his policies, or his facism, or Biden's accomplishments. And he will be sending his base to the ballot box after months of hearing about how their dear leader has been suffering in jail all this time.
He doesn't sincerely want to be put in jail, he is just saying what he thinks will rile up his base like he always does.
I think he does. Not for a long time, mind you. But even an overnight stay on a contempt of court charge.....I guarantee you he would not be put in a regular holding cell with the rest of the prisoners. He'd be "held" at an off-site location where he would be far more comfortable and still able to communicate with the outside world (And I'm not saying this because it's Trump; there's no way the Secret Service would ever allow for anything else.). At best he'd be mildly inconvenienced for a night or two. Mildly. Trump would accept that in a minute if it meant that he got to paint himself as a martyr for the rest of the campaign and fundraise off of it (Because you know the money would be flowing from the rubes like wine).
Worst case scenario for Trump is that the judge backs down on any threat to hold him in contempt, and Trump gets a new weapon to use: He can just play a game of chicken with them and dare them to do something about it. Any scenario would be a win for Trump.
Can you issue fines for contempt?
None that would matter to Trump. Even an extraordinary contempt fine wouldn't even qualify as pocket change to Trump. The guy just got slapped with one judgement for the E Jean Carroll case and had to cough up $5 million, and he was live on TV 24 hours later disparaging her again. If that's how he treats a $5 million fine, the few tens of thosuands he would have to pay for a contempt of court citation would absolutely not matter.