Note that in TFA, the continuation of this very silly statement is footnoted [6], which literally starts with "I made this joke before...", so none of us ought to be taking it seriously.
The footnote only applies to the "Chancery jail" bit, not the suggestion that the court may not want to risk a public showdown: "A showdown between Musk and a judge might undermine Delaware corporate law more than letting him weasel out of the deal would." - this sentence is after that footnote.
