Why Josephine Anwhistle fails to recognize Olaf

[TheAsh]

I always find it interesting that Aunt Josephine failed to recognize Olaf, and furthermore, that the reason she gives for not recognizing him is the lack of the tattoo on the ankle, considering her husband certainly had the same tattoo, and she was involved in VFD for years. Also, it is very strange that she trusted Olaf after one short meeting, when she is so scared and frightened of everything.

Thus I think that Aunt Josephine knew immediately that Captain Sham isn't who he said he was (especially with the ridiculous excuse of the business cards) but rather she thought that Olaf was Jacques! (or Lemony disguised as Jacques, if you think she would fully recognize Jacques.)

We know that Josephine would have been familiar with Jacques:

Aye! I would think Josephine would have told you about the Queequeg! After all, I patrolled Lake Lachrymose for years! Poor Josephine!

“Then we had Jacques!” the captain continued. “Aye, and then what’s-his-name, Jacques’s brother, and then a dreadful woman who turned out to be a spy, and finally we have Phil! Although I like to call him Cookie! I don’t know why!”

And we know Jacques had a unibrow, like Count Olaf.

In addition, in UA, the letter about the Prospero was given to somebody in The Anxious Clown, right near Josephine's home. The letter says "I will be disguised as Captain S." Now, there is a Captain Snicket in the Prospero Photo, but that isn't much of a disguise. It's possible that Josephine knew about this letter, or this Captain Disguise, and figured it was Jacques.

The proof?

Aunt Josephine held a hand over the receiver and faced the three children. “Violet, Klaus, Sunny, please go to your room,” she said. “Captain Sham—I mean Julio, he asked me to call him by his first name—is planning a surprise for you children, and he wants to discuss it with me."

Julio Sham - J.S. What are the chances that Olaf would pick those initials without being familiar with them or their significance to Josephine?

[Optimism is my Phil-osophy]

This is a good hypothesis. Unfortunately, we don't have access to Josefine's thoughts to prove it definitively. But it is important to note that even people trained by VFD to use disguises can be deceived by the disguises themselves, as happened with Madame Lulu and the Baudelaires.

[Dante]

It is a good hypothesis, but it relies on a couple of assumptions which you present as certainties. For instance, it's not confirmed that the period of years in which the Queequeg patrolled Lake Lachrymose overlapped with the period during which Jacques was a member of the crew, and nor is it clear exactly how familiar Josephine was with the vessel (and specifically with its extended crew outside of perhaps the captain) beyond the fact of its having had such a duty. Additionally, the U.A. photo you refer to does not feature a Captain Snicket, it features a Sailor Snicket (U.A. p. 95), suggested to be Lemony fleeing the country rather than Jacques. The Captain S., aka J. (p. 110), has been the subject of numerous interpretations, with others proposing that there was a "real" Captain Julio Sham, or alternatively (my own theory) that V.F.D. has a list of generic disguise names, accounting for Olaf's otherwise uncharacteristic habit of making literary allusions in his pseudonyms. In any case, although you present Olaf's choice of pseudonymous initials as "proof" of your prior claims, as a conclusion it in fact rests on the shaky veracity of your prior claims and so is supported by rather than supporting them.

[Optimism is my Phil-osophy]

House of cards.