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In season 2 of A Series of Unfortunate Events, it's revealed that Count Olaf apparently knew,

in the season finale, that 'Beverly', 'Elliot' and the half-wolf baby were the Baudelaires in disguise

!

In a world where such information is often difficult* to know, how did Count Olaf know?

Guesses:

  1. Olaf inferred from the Heimlich hospital tag that the Baudelaires had come.

  2. Olaf's discovery that the current Madame Lulu was the librarian Olivia Caliban led to his realisation about the Baudelaires.

  3. Olaf knew from the beginning because he actually has a knack for seeing through disguises as seen in the Heimlich hospital arc where he saw through Klaus' disguise as Dr Faustus.

  4. Olaf already knew that the Baudelaires got in the trunk.

  5. Esme discovered the Baudelaires and told Olaf.

  6. It's at least one of the above and then additionally, VFD people have a knack for seeing through disguises. Add-additionally, Olaf disguises himself often and thus (so, there's a one-way implication between practicing and recognising?) sees through disguises.

I think it's not 3 or 4 because

of the way Olaf reacted to the Heimlich hospital tag.

*'Difficult' here is a word which is used to avoid spoilers. I mean that...

...it is 'difficult' to see through disguises because adults are stupid or disguises are somehow that good or that good to fool adults. Thus, it is a wonder that Olaf saw through the disguise. This is kind of like how, iirc, the Alethiometer from His Dark Materials wasn't accessible to the protagonist after a certain point because of age.**

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**ETA re His Dark Materials: Apparently, it wasn't because of age. Fine. We can try an example from Kids Next Door or Harry Potter if you want. Pick any scifi or fantasy show where that has an age maximum rather than age minimum on something.

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    The only reason stupid Olaf is in any way competent is because all other adults are that much deeply stupider. This would just be another example of that. – Radhil Apr 14 '18 at 14:20
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    i think its futile to chase downvoters... but nope – Radhil Apr 14 '18 at 15:11
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    Lara lost the ability to easily use the alethiometer because the Dust had been artificially let her do so. At the end of the story, she decides to learn the "hard" way. Her age was not a factor. – Verdan Apr 14 '18 at 16:49
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    @Radhil having read all of the books, this is actually pretty much the answer. Can’t say more without spoilers. – Broklynite Apr 14 '18 at 16:57
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    @BCLC: I think he knew the whole time and the deal with the hospital tag just led to his suspicions of Lulu. Olaf was a member of VFD and much smarter than he pretends. – Shamshiel Apr 15 '18 at 13:55
1

The books are no help at all, because:

In The Carnivorous Carnival, Madame Lulu told Olaf (or so Olaf claims, at least), but in the show, she clearly would not have done so. In the books, Lulu appears for the first time at the carnival, and has been hiding from both sides since the schism. She's much less sympathetic than the Olivia Caliban of the series, so it's plausible that she would sell the Baudelaires out. This explanation is unworkable in the context of the more developed, sympathetic character we meet in the series.

Since we cannot answer this from book canon, we have no choice but to turn to speculation. As Broklynite says, Olaf's history likely makes him well-qualified to see through disguises. In both the books and the show, the Baudelaires disguise themselves using a standard VFD disguise kit, so Olaf certainly should have been able to see through it given his VFD training. We know of this history from the piano joke in "The Reptile Room," numerous Snicket flashbacks, and several other pieces of evidence in the series.

Going through your explanations:

  • I don't like (2) because the events seem rather disconnected from each other. It's quite a logical leap to go from "Lulu is Caliban" to "the freaks are the orphans."
  • I also dislike (4), because I assume the episode would be dramatically shorter if that were the case. Remember, Olaf only needs one of the Baudelaires alive.
  • (5) isn't much of an explanation, because it just moves the question to Esme. How did she know? (Also, at times Esme comes across as less intelligent than Olaf, so this arguably makes the problem worse.)
  • (1), (3), and (6) all seem reasonable given what I discussed above.
  • Nevertheless, relative to the books, this "feels like" a plot hole to me. The plot requires that Olaf only discover the truth at the very end, and we don't seem to have a solid explanation of how that would happen.
  • Thanks Kevin ^-^ – BCLC Nov 27 '18 at 1:48
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The answer is a pretty big spoiler from the books. If you haven’t yet read them, I caution you from doing so, for it shall only inevitably lead to heartbreak.

so, the world of Lemony Snicket is pretty much one of very dumb people. Functional, but dumb. Throughout the series there are hints that keep popping up- “VFD” which stands for Volunteer Fire Department. The idea is that there are a handful of quite brilliant people out there whose Volunteer to put out Fires around the world. Fires being anything from acts of war to just setting up stable societies. But every once in a while, a Volunteer decides that really, their job is to set the fires, because without that chaos, there is no change. Olaf is one of those people. He is able to get away with obvious disguises because people in this world look only on the surface and never question otherwise. But people in VFD are generally more intelligent, less trusting, and have been trained in both methods of disguise as well as how to pierce them by not just believing whatever the surface reality is. Olaf is therefore able to tell the reality at a glance. He is dumb, and arguably this is why he is more an agent of chaos, but in comparison to the rest of the world, is quite intelligent.

  • Broklynite, thanks. Are you really unable to provide an answer of reasonable speculations if nothing definite based on the TV series? In the language of probability or statistics, the books give you a deduction of 100% certainty. I am comfortable with a lower certainty, say, 95% as long as the deduction is conditioned on events in the TV series. Wait. I'll submit and edit. – BCLC Apr 15 '18 at 17:56
  • Uhuh, so my edit was rejected. Oh well. – BCLC Apr 15 '18 at 20:56
  • So, in a story of otherwise stupid people, Count Olaf is one of the smart ones.. Just like everything else in the story, it's depressing. – Verdan Apr 16 '18 at 0:15
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    @BCLC I haven’t read the books in years, but I vaguely recall the same plot point in the books. However, I haven’t watched the show more than the first episode or two. – Broklynite Apr 16 '18 at 1:26
  • Broklynite, @Verdan, to clarify in re Radhil's answer: Radhil's answer is right but incomplete because it lacks explanation and the spoiler text in Broklynite's answer is precisely how Olaf knew? I mean, series watchers really cannot deduce from previous events about how Count Olaf knew? If no: Broklynite's answer, whatever it contains, is either wrong or superfluous, and in the latter case, there should be some 'to add to Radhil's comment' clause? If yes: Then it's bad writing in the TV series? – BCLC Apr 16 '18 at 1:26

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