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So I don’t think I’ve missed it.
As you said,
But I don’t believe Massie can run in the midterms.
I admit I am wrong that he can’t be the incumbent, because technically being the incumbent just implies holding the office, not running for the office they currently hold, but in a world where a special election happens (or an appointment), and Massie takes McConnell’s Senate seat, he can not run in the midterm election.
Per Ballotpedia the deadline to file as a unaffiliated (independent) was in June.
Any special election would only cover the remainder of McConnell’s term and not the term after, which is a whole separate election that is happening in November.
My guess, after reading more about it, would be that a special election could include the two current midterm candidates AND Massie (as an independent), and that election could result in a Democrat winning. Then because the Democrats “just won” it would lower Republican voter turnout in the midterms. (Although I suspect in this scenario the midterm and special election would both take place in November, so it wouldn’t be two separate elections, but Massie would get more air time to ensure the Republican doesn’t win.)