The variance is large enough that there is no correlation in the stat from season to season. If there is no correlation, then clutch or choke is not a repeatable skill. It's a random factor. A player might have had a clutch career, but not because he is a clutch hitter.
I looked at Fangraphs' "Clutch" stat on a season by season basis for each of the players that you mentioned in your opening post, except for Montgomery because I didn't know which Montgomery you were referring to. Also, I used the "Clutch" stat rather than BR's High/Medium/Low leverage because I could see all seasons on the same page (my laziness.)
Gallo was pretty consistently bad in clutch situations, except for 2020 in which he had a positive clutch stat.
For the other players, Judge, JD, and Ortiz, there is no rhyme or reason to their season by season data. They were unclutch just as often as they were clutch.