While we have grown accustomed to members of Trumpworld being mired in lawsuits, it is worth underscoring that Giuliani is confronting extreme levels of legal and financial risk — and he has few, if any, good options. “The emotional and financial pressure of a single long-term federal white-collar investigation can take a crippling toll on any target of such an investigation,” said Paul Pelletier, a former acting chief of the Justice Department’s fraud section. “Enduring multiple investigations, in addition to bar disciplinary actions and financial pressures, creates an enormous incentive to alleviate that pressure in some way. The only logical ways I know of are to plead guilty, cooperate, or both.”…
While some experts say Giuliani, if he faces charges, will likely fold before going to jail, others are not so sure. Bromwich, the former inspector general, cautioned, “We don’t know the strength of the case prosecutors are building against Giuliani or when they will reach a decision on whether to bring charges.” And if Giuliani is charged, Bromwich said, “even in his current, diminished state, it’s hard to imagine him crying uncle. I would expect him to fight any criminal charges to the bitter end.”
One problem for Giuliani is that prosecutors have extra motivation in pursuing him, given the zealous lengths he has gone to undermine the democratic system that the Justice Department is supposed to protect. “Giuliani has made himself a very attractive target for prosecutors, because of who he is and what he’s done,” said Stephen Gillers, a New York University law professor. “Prosecutors may view taking down Giuliani as a significant career achievement.”
Gillers added, “Giuliani has more than embarrassed the department. He’s betrayed what they hold dear, and that’s a motivating factor for going after him, if the proof is there.”
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