% replaces any number of letters (la% - lake, lamp)_ replaces one letter (ca_ - car, cat)
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The Crossword Solver found 15 answers for The New York Times crossword clue punishes 9 letters. The answers have between 3 and 15 letters.

AnswerClue
PUNISHERSdisciplinarians, at times
DISCIPLESpunishes
ENTOMBpunish like Montresor does Fortunato in “The Cask of Amontillado”
BANsevere social media punishment
AGASSItennis great known as “The Punisher
BANsevere punishment
DEMONETIZEpunish, in a way, as a YouTube creator
GROUNDEDpunished for the weekend, perhaps
AGASSItennis great nicknamed “The Punisher
PRISONSENTENCES“Crime and Punishment,” e.g.?
FACETHEMUSICaccept imminent punishment
STONINGbiblical punishment
NOTVparental punishment that might be circumvented with an iPad
TYRANTS“Clever ___ are never punished”: Voltaire
LAPSpunishment for goofing off in practice, perhaps

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