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The FBI's Raid on Giuliani Puts Trump in a Deliciously Difficult Position—Which Path Will He Choose?

Tom Williams/CQ-Roll Call, Inc via Getty Images // ALEX EDELMAN/AFP via Getty Images

Donald Trump will soon find himself in an interesting legal pickle. His former personal lawyer, Rudy Giuliani, whose home and office were recently raided by federal agents and whose electronic devices were seized as a result, will likely stand accused of failing to register as a foreign agent working on behalf of Ukranian officials.

Given that he appears in fact to have been working with known Russian agents, and that what he was seeking to accomplish by falsely smearing Joe Biden posed a grave national security threat, this is actually a very serious charge that could carry up to five years in prison if he is convicted.

Giuliani's defense to such a charge will be straightforward: He will say he was working on behalf of his boss (then-president Trump), and therefore he can't be guilty of this crime. This will leave Trump with one of three basic choices.

Choice One: Trump agrees with Giuliani and admits he ordered him to try to find dirt on Joe Biden with Ukrainian help.

This outcome is highly unlikely. Trump was already impeached over this accusation, and if he were to admit now that he ordered Giuliani to seek the aid of a foreign government and Russian agents to help smear his rival in the election, he essentially would be confessing to a crime and to a conspiracy.

There is an irony here worth noting.

The fact is, Giuliani was probably operating under Trump's instruction. The trove of evidence that the Justice Department now possesses also likely confirms this, at least to some extent. It is also likely that investigators have known this for some time. Warrants to search premises and seize evidence can't simply be fishing expeditions; they must be based on enough existing evidence to demonstrate probable cause that evidence of a crime exists. That almost certainly means investigators already knew what Giuliani was up to and had strong evidence to show the judge or magistrate even before his electronic devices were seized. That evidence probably includes on whose behalf or instruction Giuliani was operating.

Trump won't be thinking about any of that, though, or how anything other than an admission will bump up against this evidence. Instead, he will want to avoid anything that ties him closer to Giuliani on the Ukraine scandal.

Choice Two: Trump refuses to answer any questions concerning Giuliani, either by raising attorney-client or executive privilege, or by pleading the Fifth.

While silence is almost certainly what Trump's lawyers would recommend, it's not likely to be what Trump does. The ex-president desperately wants to continue having political influence and, importantly, to exert that influence in the upcoming 2022 midterms. The Giuliani investigation would hang heavily over that influence if Trump simply said nothing at all.

If asked about the investigation by the press, for example, it is highly unlikely that Trump would simply refuse to answer, as that would make him look guilty in the court of public opinion. As for pleading the Fifth, though in past matters Trump has asserted it, he has also implied that people who do so have generally something to hide.

Trump once said after Hillary Clinton aides invoked their right against self-incrimination:

"The mob takes the Fifth. If you're innocent, why are you taking the Fifth Amendment?"

With Trump recently establishing his own "blog" as a funnel for his missives and misinformation to be spread across social media, especially now that his own Twitter and Facebook remain banned, Trump will no doubt use it to put his own spin on whatever transpired. As eager as he is to be in the spotlight again, it is hard to imagine Trump will choose or have the raw discipline to simply say nothing about Giuliani.

Choice Three: Trump throws Giuliani under the bus and claims that anything Giuliani did was without any direction or instruction from him.

This is by far the most likely path, given how many other allies Trump has discarded as soon as their own legal problems loomed large enough to become a headache for him. Trump's other personal attorney, Michael Cohen, quickly became a casualty of this practice after his arrest.

Things are a bit different this time, however.

Were Trump to be questioned by the FBI and deny his involvement, he might be setting himself up for a charge of making false statements to federal agents, which is itself a crime. Trump no longer has the protection of his office or the ability to delay or stall the investigation. Indeed, prosecutors might be hoping that Trump forgets that he is so exposed and then catch him in a provable lie about his involvement in the Ukraine conspiracy.

While that sounds enticing, prosecutors probably aren't very interested in using the Burisma matter to ensnare Trump. That case was already tried before the Senate, and in the mind of the public it is already in the past. Trump would no doubt make a great deal of political hay from the idea that he was "already cleared" of this charge during the impeachment "trial." Instead, if prosecutors can lean heavily enough on Giuliani on the foreign agent charge, he may provide them far more useful information as a cooperating witness—on everything from efforts to interfere illegally with the election in Georgia to Trump's role in organizing and inciting the January 6th insurrection. But for pressure to work on Giuliani, he will have to understand that Trump does not have his back and won't corroborate or support his defense.

It is somewhat ironic, then, that the Justice Department under Bill Barr insisted on delaying the execution of the Giuliani warrant until well after the election was over. This wound up meaning that Trump was no longer president when it all went down and could not pardon Giuliani for any crimes he may have committed.

Presently, Giuliani is not charged with any crime. But it is likely that he either soon will be taken in for questioning or indicted by a grand jury, and at that point Trump will have to show his hand. Prosecutors will need Trump to disavow Giuliani, or refuse to answer questions, for any pressure campaign to succeed.

So will Trump stand by Giuliani, or will he toss him under the bus, too? The way things look, I'm going with bus.