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Why didn't the Hogwarts portraits ever see any of the crimes going on during Tom Riddle's days? Or any criminals in particular?

We see many of the Hogwarts portraits interacting with students and staff members alike, and some portraits even criticize some of the actions that those students and staff members did, like Harry Potter's and Severus Snape's Lumos in the Prisoner of Azkaban. Also, the Headmaster portraits aid the current Headmaster in their duties by sharing knowledge and information to the current Headmaster, as Dumbledore, Snape, and McGonagall did.

The crimes that Tom Riddle, his friends, and, later, his followers committed could've been reported by the Hogwarts portraits to the teachers or Headmaster Dumbledore. Is there a canonical and logical reason from the books or JK Rowling herself that the Hogwarts portraits never reported a single crime to the teachers and Headmaster Dumbledore?

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    Two possibilities: 1) the crime is committed in the place without portraits 2) the crime is committed in front of a portrait of the person who ideologically agrees with the criminal (see Phineas Nigellus Black portrait, for an example). Imo, the whole "sentient portraits that can flit from one picture frame to another" wasn't well thought out. Interesting question, I can't wait to see the answers.
    – jo1storm
    Sep 21 at 9:20
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    While it seems to be contradicted heavily by the actual books, based on JKR's previous Pottermore writings portraits apparently aren't intended to have that level of awareness to them. Sep 21 at 12:21
  • Good points. As witnesses, the portraits can be compared with the ghosts, who seem to have a higher level of awareness and sometimes do reveal useful information. Sep 21 at 13:43
  • The portraits saw nothing. youtube.com/watch?v=kp9BJxFHDYI
    – Pete
    Sep 21 at 17:41
  • @AnthonyGrist "based on JKR's previous Pottermore writings portraits apparently aren't intended to have that level of awareness to them." The doors to the Hogwarts dormitories prove otherwise. Actually, all of them prove otherwise as they can move from portrait to portrait within the castle.
    – Kyle V
    Sep 21 at 18:15
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The only crimes we see Tom Riddle do while in Hogwarts are releasing the basilisk from the Chamber of Secrets and killing Myrtle. As these things both happened in the girl's bathroom, there weren't any portraits there to see him do those actions. Anyway, I'm sure Tom would've thought of portraits seeing any of his crimes (and for that matter any students in the corridors), and would therefore logically not make any trouble in a public place.

Regarding other Death Eaters, I don't think all of them made their crimes so secret, as we can see from Lily's conversation with Snape:

"...I’m sorry, but I detest Avery and Mulciber! Mulciber! What do you see in him, Sev, he’s creepy! D’you know what he tried to do to Mary MacDonald the other day?”

So the Death Eaters probably didn't really care about what trouble they got into if anyone saw what they did. And as we don't really have that much information about their actions in Hogwarts, it's a bit hard to answer if they got away with anything.

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I thought that the older generations from the wizard community would have been sympathetic to Riddle's concerns so wouldn't be inclined to report anything they witnessed.

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    This seems like a guess; do you have any evidence of portraits witnessing a crime and having a political reason not to report it?
    – DavidW
    Sep 21 at 21:07
  • I remember that the Black family had portraits in both their manor and in Hogwarts. Considering that the Black family were traditional and supported Tom Riddle their portraits in the manor would have witnessed all sorts of activity which weren't shared with anyone who enquired inside Hogwarts Sep 21 at 21:46
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    That helps; supporting details like these should be added to your answer! The more examples the better.
    – DavidW
    Sep 21 at 21:50

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