Legal Weasel
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Long before Kenneth Chesebro became Co-Conspirator 5—which is how he was identified in the indictment of Donald Trump for attempting to overturn the 2020 election—he was “the Cheese,” his nickname at Harvard Law School in the mid-80s. The moniker was based in part on a corruption of his name, which is pronounced “chez-bro,” as well as a reference to his Wisconsin roots. But there was also an element of irony in the choice, because Chesebro was anything but a big cheese—rather, a shy, awkward nerd among nerds.
So, it appears, Chesebro remained through most of his adulthood, which has rendered his current notoriety a source of bafflement to those who have known him since those days. Chesebro’s role as a legal architect of Trump’s efforts to remain in office after he lost the presidential election came to light months ago, but the indictment, which Special Counsel Jack Smith obtained from a Washington grand jury last week, places an especially harsh spotlight on Chesebro’s conduct.
As a result, his own legal status appears precarious at best. Chesebro may be indicted; he may continue to take the Fifth and hope to stay out of Smith’s line of fire. Smith’s team surely hopes he will plea-bargain and then testify against Trump. The only certainty is that in the most important criminal trial in American history, the Cheese, whether he is offstage or on, will be a central figure.
Chesebro was born in 1961 and grew up in a small town in central Wisconsin, where his father was a public-school music teacher. Ken was a competitive debater in high school and college, at Northwestern, and when he arrived in Cambridge for law school, in 1983, he looked much as he does now: the same shock of brown hair flopping onto his forehead, the same aversion to eye contact. He did well at Harvard and made Law Review, but his social skills never matched his academic achievements. “I will never forget what happened once in the typing room,” one former fellow student recalled. (In those days, students could choose to write their exams by hand in blue books or type them in a separate room on their Smith Coronas.) “First, Ken shows up with two typewriters—one and a backup—which I had never seen before,” the student went on. “Then, with about 15 minutes left in the exam, a woman starts panicking because her typewriter has broken. She notices that Ken has two, and she asks him to borrow one for the last few minutes. He says no and tells her, ‘Harvard Law School is a dog-eat-dog place.’”
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