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If he only had, all the subsequent events would have been avoided as Dumbledore would probably have solved the whole case earlier... We know Harry writes to Sirius right away to tell him about Crouch sneaking into Snape's office, we know they discuss it at length in the mountainside cave and we know that Sirius is in close correspondence with Dumbledore too. But we know for sure that Sirius did not warn Dumbledore: When Dumbledore interrogates Crouch with Veritaserum, he turned up to be completely unaware of the existence of the Marauder's Map (Crouch mentions the map of Hogwarts he took from Harry Potter, and Dumbledore answers "The map? What map?").

So how come Sirius did not write to Dumbledore to let him know of that highly bizarre fact?

It seems all the more anomalous that Sirius gets back to Hogsmeade precisely upon learning this very fact from Harry's letter. Not to mention the fact that it is Dumbledore himself who designates the mountainside cave as the safest place for him to hide! And finally, the way Sirius discusses the matter with Harry, Ron and Hermione confirms that he finds the information highly suspicious (Barty Crouch is supposed to be badly ill and, as Sirius points out, staying at Hogwarts to judge the Tournament would be the perfect excuse to keep an eye on Snape or anyone else)

The only 2 hypothesis I can think of are not convincing at all:

  1. Sirius, Harry, Ron and Hermione are all preoccupied by the fact that Dumbledore seems to trust Snape, and Sirius doesn't want to confront Dumbledore about this; but he could nevertheless have let him know the simple fact that Barty Crouch was seen at Hogwarts!

  2. Sirius doesn't want Dumbledore to know the existence of the Marauder's Map; but why would that be, since Dumbledore already knows by then that Sirius became an Animagus while he was at school? Moreover, the map would be very useful to Dumbledore under such circumstances as those in the Goblet of Fire...

EDIT: I just thought of another hypothesis and I reckon it's the right one: because Sirius, trusting Moody as everyone else, and knowing that Harry had told Moody about seeing Crouch on the map, would naturally and obviously trust Moody to tell Dumbledore about the fact! Besides, is Sirius not convinced that Dumbledore hired Moody precisely to have an Auror in the castle keeping an eye on dark wizards like Karkaroff? So, of course, Sirius would expect Moody to tell Dumbledore, not knowing Moody is an imposter. However, it remains odd that, in his further correspondence with Dumbledore, none of them ever mentioned this Crouch business.. Which would have led to Dumbledore realising that Moody was holding some information back! And starting to suspect him...

What do you think?

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    Perhaps he did. Even if he had that information then it would've been quite a leap of logic for Dumbledore to infer that Crouch Junior was alive and disguised at Hogwarts (let alone who he was disguised as). It would've been a useful piece of the jigsaw but wouldn't necessarily have solved the puzzle. – The Dark Lord Sep 4 '17 at 16:43
  • @TheDarkLord, the circumstances might have seemed fishy enough for Dumbledore to make him question Winky. Dumbledore would have easily obtained the necessary information from Winky using Legilimency, unlike Harry, Ron and Hermione who failed to. – Anya Mae Sep 4 '17 at 17:32
  • @AnyaMae I doubt Dumbledore would use Veritaserum on a House Elf unless there were really no other option. – Janus Bahs Jacquet Sep 4 '17 at 18:36
  • @TheDarkLord : No, we know for sure Sirius didn't warn Dumbledore (see my answer to TimSparrow underneath) – Silencieusement Sep 4 '17 at 19:19
  • @JanusBahsJacquet, I never said Veritaserum. He might have questioned Winky privately due to the suspicious behaviour of Barty Crouch Sr., and Winky being associated with the Dark Mark, etc. (Snape's Dark Mark had been growing clearer, and the situation does seem serious) Dumbledore is known to fish out information from various sources using Legilimency (including Hokey, the House Elf). Of course, this was the case with or without that bit of information from Sirius. Ignoring the obvious reason of plot development, it seems like something Dumbledore would or should have done. – Anya Mae Sep 5 '17 at 4:08
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First of all, we do not know if Sirius wrote Dumbledore such a letter (edit - he did not). Then, he was quite busy hiding and did not want to risk being discovered, unless absolutely necessary. Finally, Sirius would not consider Barty Sr. lurking around the school and chasing shadows very suspicious, because it was Barty's natural behavior. To suspect that it was Barty Jr. (who was officially presumed dead) would be a very unlikely leap to a conclusion.

Ok, let's assume the letter was written and sent. Upon receiving such a letter, Dumbledore would naturally suspect Barty Sr. of sneaking in his office. Knowing Barty, Dumbledore would think (as well as Sirius) that Barty is chasing shadows (as he always did). He would then consider talking to the man, not see him in a while and forget the matter altogether.

So the answer is: he did not, because he probably did not think it was very important

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    @ TimSparrow : you're actually wrong : we know FOR SURE that Sirius did not tell Dumbledore. Indeed, when the latter interviews Crouch with Veritaserum and Crouch mentions "the map (he) took from Harry Potter", Dumbledore immediately and brightly reacts : "The map ? What map ?". If he doesn't know anything about the map, he doesn't know about Crouch having sneaked in Snape's office either... So your reasoning is wrong; and that is also why my question was not : "why didn't Dumbledore make the connection", but : "why did Siruis not write to Dumbledore..." – Silencieusement Sep 4 '17 at 19:13
  • @Silencieusement I was speculating on the possibility of Sirius, not Snape, writing about that to Dumbledore. – TimSparrow Sep 4 '17 at 19:15
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    And yet it is that very event which, related to previous funny things going on, prompts his urgent return to Hogsmeade... And he discusses it lenghily with Harry, Ron and Hermione, and seems very concerned about the fact.. So it rather sounds like he thinks it is very important. I think there's a flaw in the plot here – Silencieusement Sep 4 '17 at 19:42
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    Sneaking around the school was Barty Crouch's normal behaviour? Sirius didn't consider it suspicious? Dumbledore would've thought Crouch had gone into his study? Dumbledore wouldn't have wanted to know about something so curious at a time when he was actively collating examples of curious, unexplained incidents? Are you sure about these things? – The Dark Lord Sep 4 '17 at 20:43
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    crouch was snooping around Snape to get the ingredients for the Polyjuice Potion. Seeing as Crouch (Sr) was so anti-Death Eater (or so we thought), him investigating Snape would not be out of character – Matthew Barclay Mar 11 '18 at 14:34

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