Assume you’re extremely well-heeled and under investigation or indictment for a white collar criminal offense. The crime is serious and your very freedom is at stake for a long time to come should you be convicted. The lawyer you choose won’t be one who works out of a storefront simultaneously selling insurance or his notary services. You need power in negotiating with the prosecutor or dealing with the judge. And so, you retain the top of the line who comes at a hefty price. But you need something more. You need someone who can go right to the top of the prosecutor’s office, the Justice Department itself or even the current administration.

And so, you retain a former high-ranking justice department official – maybe even a former attorney general – so he can break the logjam or get through doors currently shut to you. But even that’s not good enough. The former attorney general knows his own limitations and brings to the table someone who (maybe, informally) serves as the consiglieri to the president himself – here the term consiglieri being used in the finest sense (i.e., the president’s confidante and advisor, even if he’s not officially his lawyer). And, with you having shelled out a princely sum, the consiglieri literally brings your matter directly into the White House; indeed, the Oval Office. He has specific conversations with the president designed to release you from prison and the charges pending against you – maybe by having you, a foreigner charged with appalling offenses against the United States, “traded” back to your homeland, or another country in which you have citizenship, in exchange for an American prisoner jailed there.

This is no hypothetical – this is exactly what The New York Times (and many other news organizations) reports actually occurred when Rudolph Giuliani, after being brought into the case by former Attorney General Michael Mukasey (an attorney with an impeccable reputation), met with President Trump and then-Secretary of State Rex Tillerson. As reported, it was in those meetings that Tillerson refused Giuliani’s request for a Turkish “prisoner swap” for Reza Zarrab, who had been indicted by the Justice Department for his role in a Turkish state-owned bank’s effort to funnel more than $10 billion in gold and cash to Iran, defying U.S. sanctions designed to curb Iran’s nuclear program. Interesting, given President Trump’s open hostility to the Iran agreement reached by President Barack Obama, which Trump abrogated soon after he took office.

Now, seeking the services of a powerful lawyer – and, until now, Giuliani has certainly been that, given among other things his intimate connection to the most powerful man in the world – is certainly always worth considering, and if one can afford it, why not? After all, the greatest criminal lawyer of the second half of the 20th Century, Edward Bennett William, was nicknamed “The Man To See,” precisely because of “who” he knew and his deep rolodex, although we must not forget his virtually unmatched courtroom skill.

But “the Giuliani thing” is (or shall I say was) totally different. There’s no semblance of discretion – meetings in the Oval Office behind the back (or at least without the presence or participation) of the prosecuting U.S. Attorney (from the Southern District of New York). That’s considerably worse than those defense attorneys who call the U.S. Attorney or District Attorney directly because they have broken bread together in some former life, without having the judgment to tell the line assistant that he intends to do so. It is typically the most counterproductive maneuver a power broker lawyer can make. When a lower echelon player in one of these scenarios rightly or wrongly feels that his case has been sold down the river by a high class “fix” – which is precisely what Giuliani was trying to accomplish for Zarrab (but failed) – he perhaps becomes a disgruntled “source” who shows up at midnight on a fog-drenched bridge telling a reporter the lowdown on the dirty deed. Maybe it was Tillerson himself who leaked, or some lesser figure in the State Department or even a prosecuting attorney who discovered what Giuliani had been trying to do. How valuable are Giuliani’s chits now that this story has come to light? And you, as the client, how good will it be when you ultimately have to face the music before your sentencing judge if you’re convicted now that it is known that you hired the “best” (here a euphemism) to stop the prosecution in its tracks?

Now, for sure, there’s great benefit to a client having the absolute best team he can have by his side when fighting the all-powerful arsenal of the government. And having as a member of the team a sophisticated “insider” can indeed prove outcome determinative in benefiting the client. But, typically, it only works if it doesn’t leave participants on the government side with reason to question – or challenge, privately or even publicly – the merits of the decision-making on the part of “higher ups” who went against the recommendation of the line assistants.

In the Zarrab case, according to the Times’s reporting, the Secretary of State said “no” to the prisoner swap, and the president didn’t overrule him. Still, at day’s end the whole scenario seems sordid in the extreme: the lawyer for Zarrab – and let’s not mince words, Zarrab is an enemy of the United States and its policy to deal with its blood enemy Iran – is negotiating on his client’s behalf in the Oval Office with his prosecutor absent. Think about that for a second.

Put aside the president’s own conduct. Is it really hard to understand why the prosecutors in the Southern District of New York might now, even if reluctantly, believe it appropriate to investigate Giuliani – who once led that office with great accomplishment – for the extreme way he has “power-lawyered,” even in matters totally unrelated to Zarrab? It may well be that the de facto safe harbor he had essentially gained for himself at 1 St. Andrew’s Place based on the perception of his stature at the bar and past accomplishments may no longer obtain.

So yes, The New York Times reports that Giuliani is being investigated as to whether he violated lobbying laws in his dealings with the Ukraine, including efforts to undermine the American Ambassador there. And The Wall Street Journal reportage on the investigation is even broader, noting that Manhattan federal prosecutors are examining not only his business dealings in the Ukraine, but also his finances.

Joel Cohen, a former state and federal prosecutor, practices white collar criminal law as Senior Counsel at Stroock & Stroock & Lavan LLP and is an adjunct professor at Fordham Law School.

[Image via Andrew Burton/Getty Images]

This is an opinion piece. The views expressed in this article are those of just the author.