Icing on the cake

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One of the reasons a criminal investigation into a crime boss like Donald Trump takes time is that witnesses have to be produced to testify to his guilt in order to get a conviction – and not all witnesses are necessarily looking to do so. For instance Jack Smith appears to have obtained the cooperation of the “Trump Employee 4” named in yesterday’s new criminal charges. But Smith is also clearly looking to get the cooperation of people like Carlos De Oliveira. Since he’s not cooperating, he’s been indicted.

This doesn’t mean the story is over when it comes to De Oliveira. In fact the story is just beginning. Up to now he’s presumably been of the belief that Donald Trump could protect him in all this. But that came crashing down yesterday when De Oliveira was hit with criminal charges that’ll put him in prison for much of the rest of his life. All you have to do is read the charging document to see that there’s almost no chance De Oliveira will be acquitted at trial.

The question is how to drive that point home to De Oliveira now, so he relents and cuts a cooperation deal or immunity deal against Trump and the others. One tactic is to simply let the indictment sink in for a moment. Once you’re being arrested, charged, arraigned, and meeting with attorneys every day, you start to realize that this is your life now – and it’ll only get worse once you’re convicted.

To that end, family members and neighbors of De Oliveira are already telling CNN that they think he’s “trapped” in all of this, and that they can’t imagine how he got caught up in it. This is good. It suggests that the people in De Oliveira’s life will be inclined to try to convince him to pull himself back out of it.

With everyone who’s cut a cooperation deal, there was a prior point where they insisted (and maybe even believed) that they would never cut a deal no matter what. But that certainty starts going out the window once your life starts getting ripped to pieces in front of you.

Trump is surely still filling De Oliveira’s head with delusional fantasies about how Trump is somehow magically going to become President again, and then pardon him. But even if Trump were to get back into office – and he absolutely won’t – that would still be in 2025. This is 2023. Even in the magic carpet rescue fantasy that Trump is offering, De Oliveira would still have to sit there and rot in prison until then. And as Trump keeps getting hit with more and more charges, De Oliveira may be more likely to figure out that Trump is going to the big house, not the White House.

And so we wait, because this kind of thing is a waiting game. Jack Smith has from now, until whenever this criminal trial starts, to keep chipping away at Carlos De Oliveira (and for that matter Walt Nauta) in the name of getting one or both of them to flip in time to testify against Trump at the trial. The kicker is because there are now two Trump co-defendants, they each now have to consider the possibility that the other might flip first and get the “good” deal.

Of course there are probably more people at Mar-a-Lago who will end up criminally indicted. There’s still every reason to expect that multiple current and former Trump attorneys will be indicted for obstruction of justice, unless they’ve already cut deals against Trump. Jack Smith already has an overwhelming Espionage Act case against Trump. Anyone who flips will be icing on the cake, in terms of boosting the odds of convicting Trump even higher.

There’s also another angle to consider. At this point there’s a good chance that Jack Smith’s January 6th charges against Donald Trump will go to trial before Jack Smith’s Espionage Act case does. After all, Smith’s January 6th case will be brought in Washington DC where federal trials move quickly, and it’ll be unencumbered by classified evidence or a wacky judge.

Once people like Carlos De Oliveira and Walt Nauta see Donald Trump get convicted and sentenced to prison in Washington DC, it may finally hit them that no magic pardons are ever coming, and they could be inclined to flip at that point. These things have a way of snowballing. It’s part of why Jack Smith keeps putting so many balls in motion.

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