New developments suggest Matthew Calamari could be negotiating a plea deal against Donald Trump

| 9:09 am EDT August 21, 2021
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When New York prosecutors criminally indicted the Trump Organization and Allen Weisselberg, it was rather obviously just the opening salvo. Prosecutors were looking to pressure Weisselberg to flip on Donald Trump and the Trump family, and if Weisselberg refused to take a deal, they were always going to move on to the next person down the line. By all accounts, that person was always going to be Matthew Calamari. Now that’s in motion.

The Wall Street Journal is reporting that New York prosecutors and the Trump Organization have recently been fighting each other over document production in what had been secret court hearings. That alone makes pretty clear that the New York criminal case didn’t end with the initial indictments, and that there are more indictments coming. But the WSJ may have buried the real lede.

In the fourth paragraph, the WSJ article reveals that New York prosecutors have indeed been meeting with Matthew Calamari, “partly to determine whether his cooperation would be helpful.” The article goes on to spell out that Calamari and his son are being investigated for unreported benefits. Notably, Calamari’s lawyer is quoted as saying that prosecutors “asked reasonable questions and we are providing responsive information.”

This set off alarms for former New York Assistant Attorney General Tristan Snell, who tweeted this: “That’s not the kind of thing you say if you’re going to fight to the death — my take is that Calamari is negotiating a deal to cooperate against Trump.”

Snell is right. The only reason for criminal defense lawyers to publicly paint prosecutors as “reasonable” is if they’re looking to work with them, rather than end up fighting against them at trial. If Calamari isn’t already negotiating a deal, he certainly appears to be on that trajectory.

Of course the biggest story may be that if Calamari does close in on a deal, Allen Weisselberg will have to quickly decide whether to hurry up and cut a deal of his own first, before his leverage evaporates. Prosecutors would surely love to have Weisselberg, the ultimate insider, flip on Trump. But if Calamari is willing, they can indict and Trump with his help instead.