Deeper into the "why" of Kenneth Chesebro

After I wrote my recent column on Chesebro, I got some questions from readers, including a good one from my friend Ann Banks, that made me realize I had missed something in exploring Chesebro’s political transition. It occurred to me that he may be this kind of guy:  he goes through a blue-chip education, does well enough at Northwestern to get into Harvard Law, does well there, too, if his association with Lawrence Tribe, the famous Harvard professor and legal thinker, means anything.  But then he gets out in the real world and it’s tougher out there.  Impressing professors in college or grad school is very different from impressing people enough to get them as clients of your law practice.  Once Chesebro set up his practice in Cambridge, impressing judges or other lawyers in negotiations is much harder than getting a pat on the head from Tribe. Because of his background and where he chose to do his legal work, his friends tended to be from the liberal intelligentsia, for want of a better term, and because they were as smart or smarter than he was, they would have been hard to impress, too.  

Tribe, interviewed around the time Chesebro was indicted in Georgia, told The Guardian that when they worked together, Chesebro was “obviously bright and seemingly decent.”  Man, you want to talk about damning with faint praise, that is the sledgehammer version.  Chesebro’s Harvard Law classmates, meanwhile, eclipsed him in spades.  Elena Kagan is on the Supreme Court.  Jeffrey Toobin wrote several bestselling books, including a blockbuster on Patty Hearst, became a legal analyst for CNN, and when he wasn’t pulling his pud on camera in Zoom meetings, was a regular contributor to the New Yorker.  Tellingly, when they were all at Harvard Law, Chesebro was nicknamed by his classmates, “The Cheese.”  That’s the kind of cheap shot that both hurts at the time and sticks in your life after school.

Then at some point as he was casting around -- it looks like about 2016 -- he came across some “conservatives” and they were really easy to impress, so he began to fall in with them.  Some of the “conservatives” he encountered were apparently from the arch-conservative Claremont Institute, because in 2016, he and John Eastman, a Claremont true-believer, filed an amicus brief in a Supreme Court case involving citizenship of people living in Samoa.

Chesebro wanted attention, he wanted praise, and he found it in John Eastman and his Claremont buddies.  They’re the ones who gave it to him without reservation.  If you look at the distance from Democrat to MAGA Republican, it is a very wide, seemingly unbridgeable ideological gap.  But Chesebro wasn’t looking for a new political party or new ideology.  He was looking for people to pay attention to him.  The gap between who he was and who he became narrows considerably when the equation is personal rather than ideological.  When the goal was attention and praise from others, all he had to do was make the jump from Cambridge libs to the people at Claremont who consider themselves “conservative intellectuals,” and they were happy to give him the attention and praise he was longing for. 

Chesebro looks to be a guy who got in over his head in the crowd he was running with when it included Lawrence Tribe and Cambridge liberals.  When he switched over to John Eastman and the certifiable true believers of the Claremont Institute, things were very different.  All of a sudden, he’s a genius.  All of a sudden, he is loved.

Look at what he did for Trump in 2020:  that fake elector scheme and the memos he wrote would have gotten him an F in first year law.  But the Trump people, who included his buddy Eastman, beamed and said, give us more, give us more!  Have a gander at Chesebro’s face in this photo: 

He’s with Alex Jones, the conspiracy-salesman of InfoWars, and he is surrounded by the drooling assholes who assaulted the Capitol.  It’s a long way from Harvard Law and Cambridge liberals, but Chesebro finally found the people who would pay attention to him and think he’s great. He is genuinely happy, which was his goal all along.