#tbb:re

Before “All The Wrong Questions”

An unnamed member of V.F.D. writes a letter to secretary J. regarding the potential recruitment of a young volunteer (LSUA, p.52). The youngster in question is implied to be Daniel Handler himself (according to LSUA’s index).

Lemony meets Beatrice for the first time then sends her an apology note (TBL, LS to BB #1).

During “All The Wrong Questions”

NA (although the supplementary material FU:13SI happens between “When Did You See Her Last?” and “Shouldn’t You Be In School?”).

Between “All The Wrong Questions” and “The Bad Beginning”

Lemony writes to Beatrice about an upcoming expedition (TBL, LS to BB #2).

The official V.F.D. disguise kit manual is written (LSUA, pp.99-108). The recruitment guide (LSUA, pp.189-191) could also have been written at the same time. NB: the disguise kit manual and the recruitment could actually be much older than that. However the disguise kit manual mentions sugar bowls, which implies that it would have been written at around the same time period as the earliest mentions of the sugar bowl (first vineyard letter, LSUA, pp.84-86, see below). Note that sugar bowls are never mentioned in “All The Wrong Questions”, which seems VFD’s obsession with the sugar bowl only started after Lemony graduated and became a dramatic critic.

Lemony writes to Beatrice to warn her that he will soon be appointed as dramatic critic for the “Daily Punctillo” (TBL, LS to BB #3).

Beatrice writes a poem hidden inside the booklet of her play (TBL, last pages) but Lemony fails to notice it.

Lemony writes to Beatrice to schedule a date where he plans to ask her hand in marriage (TBL, LS to BB #4).

Lemony writes a letter regarding his childhood memories to Dr. Charley Patton ( LSUA, pp.8-21) before his intended marriage to Beatrice. An unidentified person will later make notes to this letter, remarking on inconsistencies in Lemony’s testimony.

Lemony writes a scathing review of Olaf’s new play (LSUA, p.77-79), also announcing his upcoming marriage to Beatrice.

Jacques (who is currently working inside the Queequeg) learns of Lemony’s review and writes his brother a letter, telling him 1) to go to Damocles Dock in order to plan his exile, 2) not to contact Beatrice ever again. He also mentions that Lemony should expect to get fired from the Daily Punctillo very soon.

The next day, Eleonora publishes a retractation and announces Lemony is fired (LSUA, p.80). She also announces the beginning of a new column by Geraldine Julienne.

The same week, Lemony manages to slip his rebuttal to Eleonora’s retractation into a morning edition of the newspaper (LSUA, p.81). Eleonora submits a second retraction in the evening edition (LSUA, p.82) and confirms that Geraldine’s column is scheduled to begin the next day.

The Vineyard of Flagrant Drapes writes a letter to Lemony, urging him to cancel the wedding as Olaf plans to crash it (LSUA, pp.84-86). This letter is later acquired by the Duchess of Winnipeg somehow.

After the debacle, Lemony is forced to hide in a VFD headquarter. During that time, the (real?) Captain S. writes instructions to Lemony so he can escape from the country on the Prospero (LSUA, pp.109-111), remarking on Lemony’s firing, and includes tickets with the letter (LSUA, pp.112-113). This letter and the tickets are sent to Larry in Damocles Dock so he can give them to Lemony when he gets there.

A crisis meeting is held with different members of VFD. J., the secretary, writes a live transcript of this meeting (LSUA, pp.33-47). It appears that the “J.” and “K.” characters present at the meeting are not Jacques and Kit, although Daniel Handler appears to be there. Several photographs (LSUA, pp.48-51) will later be added to this transcript. Olaf and Esme crash the meeting, threatening to light it on fire unless the volunteers agree with their demands.

After the meeting, the volunteers have no safe place left in the vicinity. Lemony has nowhere to go. He receives a break-up letter from Beatrice, brought to him by carrier pigeons, and answers back with a coded letter regarding her co-star’s possible duplicity (TBL, LS to BB #5).

Lemony then supposedly receives Jacques’ letter around that time and goes to Damocles Dock. Larry gives Lemony the Captain’s letter and the tickets.

A photograph of the ship is taken on the day it leaves port (LSUA, p.91). The Daily Punctillo publishes an article about the ship’s mysterious departure (LSUA, pp.93-95).

Lemony writes to Beatrice to warn her of an upcoming danger (TBL, LS to BB #6). It seems likely that this message was sent some time before Sunny’s birth but there’s also an argument for Violet’s and Klaus’.

During “The Bad Beginning”

As soon as her learns about the Baudelaire fire, Lemony dispatches Brett Helquist to draw the scene of the crime. Helquist draws the smoldering remains of the Baudelaire mansion and writes a letter to Lemony with said drawings enclosed   (LSUA, pp.182-183). He plans to discuss both documents at the Valorous Farm Dairy where a meeting with Lemony Snicket and photographer Meredith Heuer has been set.

Lemony writes an early draft of the first chapter of “The Bad Beginning” (LSUA, pp.177-178). Babs later receives this early draft and writes a note to Hal (LSUA, p.176) so he can add it to the Snicket file. Lemony also writes a letter to his sister (LSUA, p.192) announcing his intention to write a book on the Baudelaire case.

Between “The Bad Beginning” and “The Reptile Room”

The new dramatic critic of the Daily Punctillo (not Lemony) writes a scathing review of Al Funcoot’s play. Enraged that Olaf is being criticized, Esme writes to Geraldine Julienne to pressure Eleonora Poe into firing the dramatic critic, as well as to enquire about Jerome Squalor’s habits. The critic is fired by Eleronora Poe. Geraldine answers Esme’s letter (LSUA, p.119-120), confirming the new critic’s firing, with a menu of the restaurant at which Jerome usually eats (LSUA, p.121).

Gustav Sebald writes a movie script to warn Montgomery Montgomery of his new assistant and of the survivor of the Baudelaire fire (LSUA, pp.61-65).

The movie is shot. A photograph of a toddler helping Gustav build the snowman is taken, with Gustav not actually appearing in the picture as he was hidden behind the snowman (LSUA, p.71). A photograph of the actor playing Young Rölf is later taken (LSUA, p.53 and p.57). Other miscellaneous pictures of the production are taken during that time (LSUA, p.68, p.69, p.70).

Lemony realizes that Montgomery Montgomery does not know the Sebald code and that the plan needs to be changed. He schedules a meeting with Gustav Sebald near the Swarthy Swamp. On his way to the meeting, Gustav is spotted by Olaf who drowns him.

Lemony arrives at the appointment and waits nineteen hours for Gustav Sebald in the Swarthy Swamp. To pass the time, he writes a letter to the cheesemakers (LSUA, pp.55-60). Lemony is unaware that Gustav is actually already there, drowned at the bottom of the swamp.

Between “The Reptile Room” and “The Wide Window”

A review of “Zombies in the Snow” by Lena Pukalie (an anagram of real-life film critic Pauline Kael) is published (LSUA, p.165) and finds its way to Lemony’s commonplace book.

During “The Wide Window”

A photograph of the Baudelaire orphans on Damocles Dock is taken by a mysterious person. Two copies of this photograph later end up in possession of K./R. (who later sends it to Olivia Caliban a.k.a Madame Lulu).

Between “The Wide Window” and “The Miserable Mill”

Jacques Snicket visits Olivia Caliban at Caligari Carnival and asks her if his brother is alive. She gives him a copy of the photograph which R. sent to her, indicating that Lemony may be currently tracking down the Baudelaire orphans from his taxi. Jacques leaves to investigate Dr. Montgomery’s house as he knows that a book on the secret Mortmain Mountains is kept there. When he arrives, he is surprised to find Quigley. Jacques gives his copy of the photograph to Quigley.

Olaf’s henchmen kill Firstein in Paltryville, intent on replacing him with the Bald Man under the pseudonym of Flacutono. They use the the lumbermill’s machines to destroy Firstein’s remains.  Jacques learns of Firstein’s death and leaves for Paltryville, instructing Quigley to stay behind. In Paltryville, Jacques manages to send his investigation to the Daily Punctillo for an article. But Jacques is discovered by Olaf’s agents and has to flee. Because the body parts are unindentifiable, Detective Smith covers up the murder as the accidental death of an unknown person. Sir does not explain his foreman’s sudden disappearance to the workers. The Daily Punctillo uses Smith’s version for its final version of the article (LSUA, p.118). An earlier edition of Jacques’ article did survive (LSUA, p.117).

Jerome and Esme spend an evening together, at the end of which Esme bullies Jerome into marrying her.

Jerome schedules a wedding at the Vineyard of Flagrant Grapes where Esme hopes to receive the sugar bowl (perhaps because she expects Jacques to attend his friend’s wedding). The vineyard writes back, confirming the wedding but declining Esme’s request (LSUA, pp.84-86). Somehow the Duchess of Winnipeg later manages to get her hand on this letter. Jerome also sends a wedding invitation to Jacques Snicket. Fernald starts working as a doorman at 667 Dark Avenue in order to intercept any letter Jerome may be supposed to receive.

The Duchess fears that keeping the two vineyard letters is no longer safe for her. Unaware that Isaac Anwhistle is dead, she writes a letter to Kit Snicket, asking her to archive the two vineyard letters (LSUA, p.83).

Jacques finds out that Esme plans to marry Jerome in order to access the old V.F.D headquarter at 667 Dark Avenue. Fearing the worst, he writes Jerome a letter (LSUA, pp.122-124), but the wedding happened so quickly that Jerome was probably already married by the time Jacques found out about his engagement. Sometime during Jerome’s and Esme’s honeymoon, Jacques’ letter is intercepted by Fernald who works as a disguised doorman. Fernald and Olaf’s allies analyze Jacques’ letter and find out the village where he is hiding. 

Between “The Miserable Mill” and “The Austere Academy”

An unnamed person adds a photograph of the Quagmire triplets (with a note) to the “Zombies in the snow” file in the Sebald archives (LSUA, p.70). This is because the movie was made for Montgomery Montgomery and Quigley Quagmire eventually escaped from his childhood home to Montgomery’s house.

Lemony Snicket writes Sally Sebald to inform her of Georgina Orwell’s death. Sally answers, informing him of the circumstances in which the survivor of the Baudelaire fire was hidden (LSUA, pp.66-71). Sally also finds the photograph of the Quagmire triplets inside the file and does not understand what it’s doing there. Lemony will later replace the photograph of the triplets with a photograph of people “around the same age”.

During “The Austere Academy”

At this point in time, first editions of “The Bad Beginning” and “The Reptile” apparently already exist. We see excerpts of these two books later on in other documents. This edition finds its way to a library which has recently been overtaken by the tweed-coat-wearing librarian. This is a contentious topic as “The Reptile Room” mentions Klaus and Violet reflecting on its events “years later” even though only a few months/weeks have passed at the time of the book’s publication. One can only assume that these passages are either:

 the result of Lemony making reasonable assumptions on Klaus’ and Violet’s future,

additions which Lemony made years later as he kept updating the books with new details of his investigations (in which case what we, the readers, are reading is not the first edition of the book read by Al Funcoot’s fan, bur rather a later edition). This is plausible because “The Bad Beginning” got an updated edition called “The Bad Beginning: Rare Edition” with additional notes regarding Lemony’s more recent findings on the events depicted in the book.

Al Funcoot (probably Olaf under a pen name) writes to one of his fans, ordering him to investigate the fate of Montgomery’s collection of reptiles. The henchman goes to his local library and reads excerpts of “The Reptile Room” (LSUA, pp.147-148).

The henchman (now disguised as a cow) roams the surrounding of Lousy Lane, looking for survivors of Montgomery’s collection. The henchman noticeably hears the Dissonant Toad who is repeating something he once heard Olaf say. Supposedly the comment made by Olaf on how incovenient it is to drown someone happened the night of Monty’s murder. The toad was in the Reptile Room that night and heard Olaf kill Montgomery, after which he wondered aloud how he was going to dispose of the body. The henchman disguised as a cow also spots the Mamba du Mal as well as other reptiles. The henchman later reaches the Valorous Farm Dairy but does not dare approach the location.

The henchman disguised a cow sends Al Funcoot his own report of the events (LSUA, pp.145-153). The information from his report will later be used by Olaf’s allies to find and kill the survivors of Montgomery’s collection. Only the Incredibly Deadly Viper is now safe for now at the Valorous Farm Dairy.

Growing frustrated with his unsuccessful hunt for the Incredibly Deadly Viper, the henchman disguised as a cow finally works up the courage to ask the cheesemakers about the reptiles. Suspecting his ill intentions, the cheesemakers immediately write a postcard to Lemony so he can be warned that Olaf’s henchmen are looking for reptiles near the Valorous Farm Dairy (LSUA, pp.155-156).

Lemony writes a letter to the Duchess, announcing his intention to attend her Masked Ball (LSUA, p.144) even though the survivors of Montgomery’s collection are being hunted.

Supposedly the events of the Masked Ball happen soon after (Lemony flashes back to the Masked Ball in the beginning of the eleventh chapter of “The Austere Academy”). After the Masked Ball, Coach Genghis arrives at Prufrock Prep (fourth chapter of “The Austere Academy”).

Between “The Austere Academy” and “The Ersatz Elevator”

Jerome, who never received Jacques’ letter, writes Jacques to announce Esme their plans to adopt some children (LSUA, p.125).

Quigley, growing impatient, reads an article of “The Daily Punctillo” which describes his siblings’ kidnapping. He leaves for Paltryville.

Jerome writes a letter to Jacques Snicket, lamenting the fact his friend wasn’t present at his wedding (LSUA, p.125). Esme is planning to acquire the custody of the Baudelaire orphans during that time.

During that time, the tweed-coat-wearing librarian seems to change jobs as he now works at Prufrock Prep. Carmelita Spats runs into him, which earns him an appareance in her autobiography (LSUA, p.171).

During “The Ersatz Elevator”

The Duchess (or somebody impersonating her) writes a letter to Lemony (LSUA, pp.25-28). This letter was supposedly written during the “first few days” that the Baudelaire orphans spent with Esme and Jerome at 667 Dark Avenue (mentioned in Chapter Three of “The Ersatz Elevator”), before Gunther’s arrival.

At the In auction, the Esme Squalor fan club bids on the corpse of the Mamba du Mal. This is reported by the In Auction catalog (LSUA, p.164) and Lemony includes a page of the catalog in his commonplace book.

Lemony sends the cheesemakers a note (LSUA, p.159) with the contents of his commonplace book (LSUA, pp.161-175). The excerpts contained in the commonplace book are intended to warn the cheesemakers of the reptiles of montgomery’s collection and the secret messages/codes they can communicate. One of the excerpts is a newspaper describing how the Mamba du Mal was killed and auctioned.

At the Valorous Farm Dairy, the meeting planned by Meredith, Brett and Lemony goes haywire as they have been spotted by the villain disguised as a cow. The dairy is burned down by the villain but Meredith manages to take one last photograph of the dairy before the fire (LSUA, p.185). The three volunteers flee. Lemony leaves a copy of his drawing of the burned down Baudelaire mansion behind in the commotion.

Detective Smith covers up the arson when reporters of the Daily Punctillo come to investigate the fire. He provides the reporters with Brett’s drawing, unaware that it actually concerns the Baudelaire mansion. The drawing may have ended up in the archives of the Daily Punctillo. The Daily Punctillo publishes an article on the “accident” (LSUA, p.184).

During “The Vile Village”

Lemony receives the suspicious letter from the Duchess at Veblen Hall while he’s interviewing witnesses about who was driving the car on the day the Quagmire triplets were smuggled out of the city by Olaf. He fears that someone may be impersonating the Duchess and writes a note about it (LSUA, p.30).

While the Baudelaire orphans are working at the Village of Fowl Devotees, Arthur Poe meets his sister Eleonora Poe in Damocles Dock. Their conversation is recorded by a mysterious individual (LSUA, pp.134-137). The transcript of the recording is later found by an unnamed individual.

During “The Hostile Hospital”

Olaf (under the alias of Al Funcoot) knows that the Baudelaire orphans are probably somewhere in the Hinterlands and that they’ll soon try to use a telephone or a telegram machine. In order to thwart them, he writes to Eleonora Poe under the alias of Al Funcoot, convincing her to publish articles about the danger of telephone poles and fake telegrams, and later writes to an unnamed person about said article. Esme also manages to phone/write Geraldine Julienne, ordering her to lock up Eleonora Poe once the articles are published.

Eleonora writes to Arthur Poe, warning him of the danger of fake telegrams. The telegram sent by the Baudelaire orphans in the Last Chance General Store (LSUA, p.140) reaches Arthur’s bank some time later and is as such ignored.

During "The Carnivorous Carnival”

While the Baudelaire orphans try to use the phone at Caligari Carnival, the unnamed person chops down the telephone poles. This ends the connection, leaving the Baudelaire orphans confused as to why the person on the other end isn’t responding anymore. Later on, the unnamed person writes back to “Al Funcoot” (LSUA, p.132-133), thanking him for the article.

Kit roams the financial district looking for scraps of newspapers. She writes a note about that to the cheesemakers (LSUA, letter on pp.75-76). The note and the scraps of newspapers are later found by an unknown person (LSUA, note to file on p.75).

During “The Slippery Slope”

Geraldine Julienne locks up Eleonora in the basement of the Daily Punctillo’s building. Eleonora sends a telegram to her brother (LSUA, p.141), but the message is ignored by Arthur Poe on the account of her article.

During “The Grim Grotto”

As he’s following the Baudelaire orphans’ footsteps, Lemony writes a letter to his sister Kit Snicket, instructing her to meet him at the Hotel Denouement, and slips it into the pages of the manuscript (end of Chapter Five) of “The Slippery Slope”. It’s extremely unlikely Kit ever received the manuscript as she seems to believe her brother is dead in “The End”. Indeed the V.F.D. meeting scheduled at Hotel Denouement happens during “The Penultimate Peril”, which would leave barely a day for said manuscript to be forwarded to Kit. One can only assume that the letter was kept within the manuscript and never removed (for sentimental reasons?). Interestingly the letter does not specify a date and “Hotel Denouement” could refer to the underground library beneath the pond rather than the building on the surface, which means that said meeting could have been scheduled much later than the building’s eventual destruction.

Arthur Poe sends a thank-you letter to Eleonora (LSUA, pp.138-139), including the two telegrams he received (LSUA, pp.140-141).

During “The End”

Remora slips on a banana peel and quits his job at Prufrock Prep. Kit Snicket is hired to replace him and teaches at Prufrock Preparatory School for a few days. This supposedly happens during the “days” the Baudelaire orphans live with the Islanders doing pretty much nothing on the Island (this undefined time period is described in Chapter Five of “The End). A photograph (LSUA, p. 127 and p. 142) is taken of Kit “supervizing” the children during gym class. Genghis and Tench no longer teach at Prufrock, so without anyone to teach them the Prufrock students just sit around looking at a camera during their gym class. During that time, Kit also seems to write a note (LSUA, p.154) about receiving the postcard intended for Lemony by the Prufrock librarian.

The Daily Punctillo publishes an article warning parents about their children reading forbidden books. The Spats parents send that article to Nero who subsequently fires Kit Snicket and writes back to the Spats parents in gratitude (LSUA, pp.129-131).

After “Chapter Fourteen”

Lemony eventually publishes an updated edition of “The Bad Beginning” with additional notes (The Bad Beginning: Rare Edition) in which he announces his intention to release the thirteenth and final volume of “A Series Of Unfortunate Events”.

Lemony is officially declared by the authorities. The Daily Punctillo publishes an official declaration of death, announcing a burial even though no body was identified (LSUA, p.3, see also the back cover with Lemony’s note). Lemony attends his own burial where photographs are taken (LSUA, p.4 and p.7). Lemony writes a note to explain the photograph and the Daily punctillo clipping and adds it to the Autobiography file (LSUA, pp.5-7).

Beatrice Baudelaire Jr eventually learns of his uncle and his research on the Baudelaire file. She starts tracking him down and sends him several letters (TBL, BB to LS #1, #2, #3, #4 and #5). Lemony does not answer these letters as he believes the author of these letters to be Esme impersonating Beatrice Baudelaire Sr.

Beatrice Baudelaire Jr eventually meet in person at a party. During the party, Beatrice Baudelaire Jr writes her uncle an apology note (TBL, BB to LS #6). Daniel Handler later writes about this party (LSUA, pp. ix-xvii and p.193) and the autobiography is finally published.

How Count Olaf voices his concerns (and why it matters)

It’s difficult to attest to what is going on in Klaus’ mind in Olaf’s final moments: his reaction is more emotional than rational. He doesn’t explain why Olaf is guilty, he just believes it on an almost spiritual level. This is a theory that Klaus has held onto for a very long time. The Baudelaire orphans know that Olaf is an arsonist since their aunt Josephine died. Olaf straight-up bragged about it to their faces:

Mr. Poe frowned, and coughed into his white handkerchief. "That's enough of your revolting talk, Olaf," he said sternly. "We've caught you now, and there's no way you'll be getting away. The Lake Lachrymose Police Department will be happy to capture a known criminal wanted for fraud, murder, and the endangerment of children." "And arson," Count Olaf piped up. [The Wide Window, Chapter Thirteen]

So from then on the Baudelaire orphans had serious reasons to believe that Olaf had burned down their home. Why is this never discussed throughout the series? Probably because the idea of their parents’ murder is so horrid, so unthinkable that the children prefer not to talk about it. It takes Ishmael committing genocide, Kit Snicket going into labor in an unsafe area and Olaf’s insistence that he was a competent guardian for Klaus to truly lose his temper and admit the truth he’s tried to hide for almost a year.

However, the Baudelaire orphans should know better. They’ve had more than enough to know that every time he’s started a fire or committed a horrible crime of any sort, he’s bragged about it. He only hides his involvement when an authority figure, legal representative or person he wants to manipulate is in the vicinity. There is no such person on the beach as he questions Klaus’ assertion, in fact he is not even aware of Kit Snicket’s presence, which is only brought up later in the conversation.

However, absence of evidence is not evidence of absence. When Olaf is confronted by an incorrect accusation of arson, he denies it unambiguously.

"I had Omeros keep this weapon handy," Ishmael said, "instead of tossing it in the arboretum, because I thought you might escape from that cage, Count Olaf, just as I escaped from the cage you put me in when you set fire to my home." "I didn't set that fire," Count Olaf said, his eyes shining bright. [The End, Chapter Eleven]

Notice how Olaf never denies putting Ishmael into the cage, his dismissal specifically concerns the arson. Considering that Ishmael is currently holding Olaf at harpoon-gun-point, his words are chosen very carefully as to not anger him even more. On that topic, it’s interesting to note that the Baudelaire orphans have picked up on one of Olaf’s tics: his eyes shine brightly whenever he distorts language to make a sinister joke.

His eyes were very, very shiny, which made him look both hungry and angry. "Hello, my children. Please step into your new home, and wipe your feet outside so no mud gets indoors." As they stepped into the house, Mr. Poe behind them, the Baudelaire orphans realized what a ridiculous thing Count Olaf had just said. The room in which they found themselves was the dirtiest they had ever seen, and a little bit of mud from outdoors wouldn't have made a bit of difference. [The Bad Beginning, Chapter Two]

"If I know you, Olaf," said the man with the hook-hands, "you'll figure out a way to get at that Baudelaire money." "We'll see," Count Olaf said, but his eyes were shining bright as if he already had an idea. [The Bad Beginning, Chapter Four]

"Mr. Poe told me," Count Olaf said, "that you appeared to be having some difficulty adjusting to the life I have so graciously provided for you. I'm very sorry to hear that." The children looked at Count Olaf. His face was very serious, as if he were very sorry to hear that, but his eyes were shiny and bright, the way they are when someone is telling a joke. [The Bad Beginning, Chapter Six]

Count Olaf's eyes grew very shiny, but he continued to smirk at Klaus. This was surprising. Klaus had guessed that once he announced what he knew, this dreadful man would have been very angry, even violent. After all, he'd had a furious outburst just because he'd wanted roast beef instead of puttanesca sauce. Surely, he'd be even more enraged to have his plan discovered. But Count Olaf just sat there as calmly as if they were discussing the weather. [The Bad Beginning, Chapter Eight]

"Where can she be indeed?" said a voice behind them, and the two children turned around. Count Olaf was standing in the doorway, watching Violet and Klaus as they searched the room. His eyes were shining brighter than they ever had, and he was still smiling like he'd just uttered a joke. [The Bad Beginning, Chapter Nine]

So in the above passage Olaf is definitely mocking Ishmael (a part of him is certainly toying with him to see if he has the guts to spill Olaf’s and spread the deadly spores of the Medusoid Mycelium). But his eyes do not shine when Klaus confronts him about his parents’ murder. Olaf was is, in fact, telling a joke when he tells the Baudelaire orphans they did not know anything about the fire which destroyed their home. He is not being opaque on purpose or playing mind-games. He is voicing legitimate, sincere concerns and grievances.

What Klaus believes (mistakenly)

Klaus does not explain why on Earth Olaf would want to kill the Baudelaire parents, but given what he knows at this point in the series, he can easily imagine three main motives:

PROFIT Killing off the Baudelaire parents would allow Olaf to gain custody of their children and from then on concoct schemes to steal their massive inheritance.

REVENGE Olaf’s parents were assassinated by Bertrand and Beatrice and Olaf wanted their children to endure the pain he felt after his own losses.

DUTY Olaf is part of the side of V.F.D. run by the Man With Beard But No Hair and the Woman With Hair But No Beard, two fanatics who terrify him and burn down buildings of rich children on a regular basis. If they ordered him to kill Bertrand and Beatrice (whom they have described as their enemies), Olaf would be compelled to obey.

Naturally, none of these motives are mutually exclusive. In fact, they combine quite well. Many mansions of rich families have been burned down because of V.F.D.’s schism and unifying theories have been proposed to explain why. Basically, Olaf’s motives could be summarized as such:

V.F.D. used to finance itself by kidnapping rich children and burning down their parents’ home, after which said young volunteers would be brainwashed into using their own fortune to help the organization (Link). Beatrice and Bertrand killed Olaf’s parents so that V.F.D. would gain a rich volunteer ready to finance their cause (Link). Then the schism happened: some remorseful volunteers (such as Bertrand and Beatrice) rejected the system altogether and vowed never to use violence again, while people like Olaf decided to steal fortunes for their own profit rather than that of the organization (Link). Olaf saw Beatrice and Bertrand as hypocrites who had never been truly punished for their actions and as soon as his two bosses allowed it, he decided to inflict on the Baudelaire orphans what had been inflicted upon him.

Klaus is certainly missing some pieces of the puzzle but has enough material to theorize that this is what truly happened. And it’s certainly what many readers of the series believe about Olaf, too.

Except Olaf’s reaction suggests that this interpretation is completely wrong. So what then? Was there a completely different reason to burn down the Baudelaire mansion? Why did Beatrice and Bertrand have to die?

In a predictable and unfortunate turn of events, it all comes back to the sugar bowl.

The timing of the Baudelaire fire (and its implications)

The first point we must examine is the timing of the event. We know that the Baudelaire parents and Olaf were enemies well before Violet was born. If Olaf hates them so much, why did he wait so many years to enact his revenge? How could Bertrand and Beatrice expect to keep their children safe in a city where their arch-nemesis could roam freely, in the public eye? Somehow, they must have had reason to believe Olaf wouldn't dare attack them. The most obvious answer is that Beatrice was the last known owner of the sugar bowl.

"Then you know all about the sugar bowl,” Esmé said, “and what’s inside. You know how important that thing was, and how many lives were lost in the quest to find it. You know how difficult it was to find a container that could hold it safely, securely, and attractively. You know what it means to the Baudelaires and what it means to the Snickets.” She took one sandaled step closer to Dewey, and stretched out one silver fingernail-the one shaped like an S-until it was almost poking him in the eye. “And you know,” she said in a terrible voice, “that it is mine.” “Not anymore,” Dewey said. “Beatrice stole it from me!” Esmé cried. “There are worse things,” Dewey said, “than theft.” [The Penultimate Peril, Chapter Nine]

As Dewey puts it, this put her in a position of power over Olaf, who wants it very badly. It's easy to imagine that he was condemned to simply observe the Baudelaire parents from afar, in the hope of learning where they were hiding the sugar bowl.

“It doesn’t matter, Baudelaires,” Jerome said. “Olaf won’t dare unleash the Medusoid Mycelium unless he gets his hands on the sugar bowl, and he’ll never find it.” [The Penultimate Peril, Chapter Eight]

Daniel Handler wrote a little-known supplement called "The Dismal Dinner" where he reveals important information about what happened shortly before the Baudelaire fire. The sugar bowl was being shown around in the Baudelaire mansion some days before the fire, and Olaf was watching. This means that there was a short lapse of time during which he more or less knew where the sugar bowl was hidden, before it was taken away someplace else. Olaf had a miraculous chance of getting his hands on the item, one and only one. This must have something to do with the fire.

My discovery of a torn pant leg shows that Sunny, an infant and the youngest Baudelaire child, played a key role in the dinner party held at the Baudelaire mansion quite some time before it was reduced to a smoking pile of rubble. Third-hand reports suggest that just after the sugar bowl was placed on the table, Sunny shrieked, "Funcoot!”, which either meant “My gums hurt!” or “I believe I may have seen someone lurking outside.” [The Dismal Dinner, part 3.]

Recent discoveries support my suspicions about the fateful event hosted by the Baudelaire parents before their death. Near the end of the meal, baby Sunny Baudelaire looked out the window and began to cry with a clarity and force that would soon characterize her ability to bite things. Her cries alarmed a number of guests who were in the process of passing around the sugar bowl. [The Dismal Dinner, part 4.]

But there is also another event which occurs shortly before the Baudelaire fire, this time revealed in the additional notes of "The Bad Beginning: Rare Edition". It concerns another fire, that of ther Royal Gardens, which happened some time before the start of the series. To put it plainly, Olaf failed to burn down a place where he was attempting to steal a poisonous plant, and Jacques reported it in the hope that the authorities would put two and two together and realize that his brother Lemony had been framed for Olaf’s crimes. You can read all about this theory here: (Link).

p.18 [The Baudelaire orphans] passed an enormous pile of dirt where the Royal Gardens once stood. For more information on the destruction of the Royal Gardens, interested parties might turn to the following articles in The Daily Punctilio, the city’s newspaper: “Arson suspected in Destruction of Royal Gardens,” by Jacques Snicket, and “Absolutely No Arson or Any Other Suspicious Thing Associated with the Royal Gardens, which Simply Burned to the Ground and Then Were Covered in Dirt Due to Wind, Says Official Fire Department,” by Geraldine Julienne. [The Bad Beginning: Rare Edition, p.175]

So two very important things happen a few days before the Baudelaire fire:

Jacques is working hard to prove that Olaf is an arsonist, and Justice Strauss is going to be assigned on the case.

Count Olaf is aware that the sugar bowl is being kept inside the Baudelaire mansion.

These two facts combine to explain what may have happened on the morning of the fire.

But most important is the fact that Olaf is indeed implied to have been present inside the Baudelaire mansion on that day…

p.6 One of the things Violet, Klaus, and Sunny really liked about their parents was that they didn’t send their children away when they had company over, but allowed them to join the adults at the dinner table… The Baudelaire table was not used exclusively for dinner. Its surface was handy for unrolling maps, completing jigsaw puzzles, and tracing the faces of people from photographs. One thing I remember from my time at the table was that it was always necessary to use a coaster underneath one’s beverage so as to not leave an unsightly ring on the wood. [The Bad Beginning: Rare Edition, pp.171-172]

p.98 But Count Olaf just sat there as calmly as if they were discussing the weather. Certain kinds of weather-severe rainstorms, for instance-have a dampening effect on fires, which is displeasing to arsonists. There have been reports of alleged arsonists so reportedly displeased with the weather that they have been rumored to pound their beverages on an unprotected wooden table. [The Bad Beginning: Rare Edition, p.179]

…and that he was apparently invited there by the Baudelaire parents:

p.2 The three Baudelaire children lived with their parents in an enormous mansion at the heart of a dirty and busy city, and occasionally their parents gave them permission to take a rickety trolley-the word “rickety”, you probably know, here means “unsteady” or “likely to collapse”-alone to the seashore… On that particular occasion, the Baudelaire parents not only gave their children permission but encouraged them to leave the house, as the adults had some pressing business to attend to. This business was delayed indefinitely due to death. Also note that the trolley has since collapsed, and its remains were recycled into the foundation of a hotel. [The Bad Beginning: Rare Edition, p.171]

pp.12-13 Here and there, the children could see traces of the home they had loved: fragments of their grand piano, an elegant bottle in which Mr. Baudelaire had kept brandy, the scorched cushion of the windowseat where their mother liked to sit and read. Curiously enough, Mr. Baudelaire’s brandy bottle was found on the remains of the dining table, with no coasters nearby. This would indicate that either the coasters were burned beyond recognition, or the Baudelaires had received a visitor who had no manners whatsoever. [The Bad Beginning: Rare Edition, pp.173-174]

There seems to be a number of odd coincidences there. With their knowledge of the sugar bowl’s relevance and the Jacques’ ongoing investigation of Olaf’s crimes, the Baudelaire parents actually have a lot of control over the situation at this point. Is it possible that they lured Olaf into their house? Was his presence part of a secret plan?

Why the Baudelaire fire resembles the Denouement fire (for all the right reasons)

"A Series of Unfortunate Events" largely deals with the problem of history repeating itself, particularly when it comes to the cycles of violence. Sons and daughters follow in their forbearers’ footsteps and commit the same kind of mistakes, never learning anything. Near the end of the saga, the Baudelaire children discover that Olaf was orphaned by their parents for something related to V.F.D., and that he seems to do what he does based on retribution. Furthermore, the schism which broke the organization is followed by several smaller, similar schisms: the separation of Klaus and Fiona, the mutiny of the Islanders, etc. Many events of the past and present are explicitly presented as parallel to each other.

In many ways one would think that, the most logical way to uncover the truth about the Baudelaire fire is to compare it to a similar fire. Let's see what we know:

It had something to do with the sugar bowl being exchanged there and Olaf wanting to get his hands on it.

The fire happens in relation to a big investigation regarding Olaf’s crimes.

One or several characters may have survived and their fate is left ambiguous by Lemony in the narration. Lemony himself might have been there.

The existence of a secret underground complex changes the entire meaning of the event.

As the similarities pile up, it becomes clear that the set-up of the Baudelaire fire clearly mirrors the one which destroyed Hotel Denouement. And there is reason to believe that the sugar bowl is actually a red herring, a sinking lure that the “noble” side of V.F.D. uses to get the other side where they want them, when they want them (Link). The entire sugar bowl chase in “The Penultimate Peril” is actually an elaborate trap set up by Dewey and his allies to arrest Olaf and his allies, and to put them on trial in the Hotel Denouement’s lobby where all evidence of their crimes will be presented to the judges of the High Court.

The Baudelaire fire was a trial version of the Denouement fire. The Baudelaire parents made sure that Olaf knew that the sugar bowl was being kept there, to use his greed against him. Then they invited him into their home on a false pretext, knowing he would waste time trying to find the Vessel For Disaccharides. In the meantime, Jacques was supposed to present the results of his investigation to the police. The authorities would then come to the Baudelaire mansion and arrest Olaf.

This scenario is key to understand why the building eventually caught fire.

Why Olaf burned down the Baudelaire mansion (as he tried to retrieve the sugar bowl)

There's a particularly strange detail about the scene of the crime which everyone in the series overlooked: the broken pieces of the brandy bottle. Now, anyone who read the un-Authorized Autobiography can tell you that brandy is traditionally drunk at V.F.D. committee reunions. So the fact that the bottle is highlighted by Handler, and presented out of its liquor cabinet, must be significant. Firstly, it reinforces the idea that some discussion related to V.F.D. was going on while the children were having fun at the beach.

pp.12-13 Here and there, the children could see traces of the home they had loved: fragments of their grand piano, an elegant bottle in which Mr. Baudelaire had kept brandy, the scorched cushion of the windowseat where their mother liked to sit and read. Curiously enough, Mr. Baudelaire’s brandy bottle was found on the remains of the dining table, with no coasters nearby. This would indicate that either the coasters were burned beyond recognition, or the Baudelaires had received a visitor who had no manners whatsoever. [The Bad Beginning: Rare Edition, pp.173-174]

J— Please pass the brandy. [Lemony Snicket’s un-Authorized Autobiography, p.37]

After the pudding, the older gentleman of my acquaintance and I retired to an enormous, imposing living room to enjoy and after-dinner brandy, and the arcane smile returned to his face as a number of older gentlemen not of my acquaintance joined us, clearly for some sort of meeting. [Lemony Snicket’s un-Authorized Autobiography, p.xiv]

Secondly, however, it brings up a much more salient point: why was the bottle broken? Glass melts easily under fire, and in fact Daniel Handler makes a point of showing a glass instrument which has melted because of the damage caused by the heat. Alcohol is flammable, so a brandy bottle should burn even more easily as the liquid ignited. And yet the bottle is clearly well-preserved enough for the children to recognize it as their father's brandy bottle immediately. It's in shards, so it would have to be barely burned for any identification. How is this possible?

The solution to this problem is that Olaf poured the brandy out of the bottle on a particularly flammable object (a book?), and used his matches to light a fire in the Baudelaire library. He then kept the empty bottle on his person as he ran to the other side of the house. This side of the house was less affected by the fire as the fire department had arrived by the time the flames caught up with him.

"The fire department arrived, of course," Mr. Poe said, "but they were too late. The entire house was engulfed in fire. It burned to the ground. " Klaus pictured all the books in the library, going up in flames. Now he'd never read all of them. [The Bad Beginning, Chapter One]

Olaf's main goal was to escape, yes, but he also had a secondary objective in mind: in the heat of the brazier, the sugar bowl would be threatened and the Baudelaire parents would have no choice but to retrieve it from its safe. It was the quickest, easiest way for Olaf to learn where it was hidden and to get his hands on it. This tactic is used with some success by Sherlock Holmes in the story "A scandal in Bohemia".

The Baudelaire parents soon realized that a fire had started in their home and decided to split. Beatrice went to the library where she attempted to salvaged as many V.F.D. documents as she could, and to retrieve the sugar bowl from its hiding place. The Baudelaire library indeed holds many documents precious to V.F.D. and the Baudelaire parents were always afraid that a fire would destroy them:

"Our mother would get mad, too," Klaus said. "Remember, Violet, when we left the window of the library open, and that night it rained?" "She really flew off the handle," Violet said, using a phrase which here means "became extremely angry." "We spoiled an atlas that she said was irreplaceable." "You should have heard her yell," Klaus said. "Our father came down from his study to see what was the matter." "And then he started yelling, too," Violet said, and the Baudelaires paused and looked at one another uncomfortably. [The Grim Grotto, Chapter Seven]

"And sometimes you burn the toast," Klaus said, and they smiled. They were both remembering a time when the two of them got up early to make a special breakfast for their parents. Violet had burned the toast, and their parents, smelling smoke, had run downstairs to see what the matter was. When they saw Violet and Klaus, looking forlornly at pieces of pitch-black toast, they laughed and laughed, and then made pancakes for the whole family. [The Bad Beginning, Chapter Three]

Bertrand, meanwhile, ran after Olaf to prevent his escape and to make sure he wasn't following Beatrice to the sugar bowl's hiding place. Olaf was apprehended by Bertrand but broke the empty brandy bottle to make a shiv, and stabbed him in (debatable) self-defense. Bertrand fell to the floor as he bled from the stab wounds and Olaf jumped out a window. His body would later be destroyed by the flames. Beatrice, meanwhile, got badly burned trying to secure the sugar bowl and her books and soon found herself trapped. Her only escape was the secret passageway under the house, where she remained for quite some time. For more information on how Beatrice could have survived the fire, read this theory: (Link).

How other passages of the series mirror the event (through symbols)

There is indeed reason to believe that the brandy was used to ignite the fire and that its broken pieces were used to create a shiv: the plot quite literally spells it out for us. In "The Bad Beginning", Klaus and Violet find themselves trapped in Olaf's lair. The only items at their disposal are Olaf's empty wine bottles, scattered around. Violet Baudelaire, in a typical display of thuggish swagger, suggests flaming alcohol and a shiv as an escape plan. And the Baudelaire fire happens in the same book, too! How fitting would it be for the Baudelaire children to re-enact the method that Olaf used to burn down their house... to burn down his own house?

"If we had any kerosene," Violet said, around noon, "I could make Molotov cocktails with these bottles." […] "They're small bombs made inside bottles," Violet explained. "We could throw them our the window and attract the attention of passersby." […] "We could break these bottles in half," Violet said, "and use them as knives, but I'm afraid that Count Olaf's troupe would overpower us." [The Bad Beginning, Chapter Eleven]

The similarities do not end there: let's go back to the Hotel Denouement fire. How did Olaf light it, exactly? A burning book, right next to dangerous chemicals. The scene is described as unsettling. Part of that, of course, has to do with the fact that our protagonists value education and that autodafés bring up very distasteful connotations. On another level, however, it's possible that this method of arson subconsciously reminds them of the way Olaf destroyed their own home. It's no wonder they bring up this possibility in the next book. The lighting of the book acts as a triggering event: it's the moment the children actually admit to themselves that Olaf probably murdered their parents.

The Baudelaires leaned forward to see if they could read what the injustice expert had written, and caught only the word "passageway" before Olaf lit a match and tossed it expertly onto the page. The paper caught on fire at once, and the book began to burn. […] "We'd best get away from here," Count Olaf said, breaking the silence. "In my experience, once the flames reach the chemicals, the fire will spread very quickly. [The Penultimate Peril, Chapter Thirteen]