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3 reasons why the Chesebro plea deal is a win for both sides

The Fulton County DA didn't make a deal because her case against Chesebro was weak; rather, she wisely decided to hold her cards for the bigger fish.

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On Friday morning, Judge Scott McAfee was beginning the often arduous process of selecting a jury for what was supposed to be the first trial in Fulton County District Attorney Fani Willis' sprawling indictment of those who allegedly tried to overturn the 2020 presidential election in Georgia.

But around lunchtime, McAfee received news that not only changed his day but his next few months: Attorney Kenneth Chesebro, the alleged mastermind of the so-called fake elector scheme, had agreed to plead guilty to a single count of conspiracy to commit the filing of false documents.

Within minutes, social media exploded with hot takes, with some suggesting Chesebro’s plea is less an indicator of his guilt and more proof of the weaknesses of Willis’ case.

But as a former litigator with experience in white-collar defense and government investigations, I don't buy that, and here's why you shouldn't either.

First, trials are expensive for everyone involved — and that’s especially true of a trial expected to last five months or more. In addition to Chesebro’s own legal fees — and it’s unclear who, if anyone, other than Chesebro contributed to his legal defense costs — trying Chesebro to verdict would have been costly for the Fulton County DA's office too.

The difference is that the costs they would have incurred are not primarily financial, but ones of resources and strategy. A trial would have consumed the core case team for months while forcing others in the office to litigate pretrial motions and discovery issues with the remaining co-defendants.

More significantly, it would have given those co-defendants — including Donald Trump, Rudy Giuliani, John Eastman and Mark Meadows — a preview of the DA’s overall racketeering case.

Second, while many legal experts believe Chesebro would have been convicted at a trial, in part because his own legal memos would have been used as evidence against him, going to trial would not have been without uncertainty for the DA. Meadows’ bid to move the case to federal court is still pending in the 11th Circuit, which sought supplemental briefing in light of a recent opinion. The question of whether removal for one co-defendant means removal for all is also open. And that means that the DA's team could have tried Chesebro to a verdict, only to have that conviction overturned not because of the evidence but simply because the trial should have been in a different court. Ouch.

Third, Chesebro’s value as a witness against the top-tier defendants cannot be understated. Although Eastman is better known and more maligned for his later-stage advocacy that then-Vice President Mike Pence discount certain slates of electors, Chesebro was the alleged architect of the seven-state, fake elector strategy. And in that unpaid, self-appointed role, Chesebro worked with multiple co-defendants — from Giuliani and Trump campaign official Mike Roman to Georgia fake electors, three of whom are themselves defendants — to execute it.

Put another way, Chesebro, who allegedly devised the scheme, helps connect those who organized it and those who implemented it on the ground.

Make no mistake: I don't believe this was Chesebro's plan all along, even though demanding a speedy trial gave him some leverage he might otherwise have lacked. In fact, his lawyers, Scott Grubman and Manny Arora, put up a good fight, filing a slew of potentially case-ending motions. But ultimately, after fellow MAGA lawyer Sidney Powell pleaded guilty on Thursday, Chesebro was cornered. Being the sole defendant in a monthslong racketeering trial where he allegedly outlined the alleged crime in writing, several times over, was no one’s idea of a smart move.

And Willis? She’s much more interested in holding her cards and securing Chesebro's cooperation than in his serving time. So everybody wins. Everybody, that is, except several of the 16 remaining co-defendants.