Count Olaf's associates are, along with Count Olaf, the main antagonists of A Series of Unfortunate Events. Many of them are conspiring to plot a way to obtain the Baudelaire Fortune, although others follow Olaf for other motivations. Many of them are on the fire-starting side of V.F.D. Some of Olaf's associates are henchpeople, like the Hook-Handed Man, and some have other relations to him, such as Carmelita Spats being his adopted daughter.
Through the course of the series, Count Olaf has had a total of seventeen associates (but only five actual henchpeople); eventually each associate either left Olaf for dead or was killed. By The End, Count Olaf is working on his own, with no associates to assist him. For the first seven books, in each book only one associate is helping Olaf, apart from The Bad Beginning when they all appear.
Original "Theater Troupe"
Fernald, the Hook-Handed Man
Fernald is the longest associate Count Olaf ever had. Fernald has hooks for hands and it is unknown how he lost his original hands. He was about to leave Olaf in The Slippery Slope by being caught in a net, but he escaped. He left him in The Grim Grotto when he found his sister, Fiona, in the Queequeg submarine, when they escaped Olaf with the Baudelaires. But shortly after, Fernald and Fiona betrayed the Baudelaires and worked for Olaf again. However, in The End, it is mentioned that the two betrayed Count Olaf for good, but his fate was eventually left to The Great Unknown. Fernald used to be on the fire fighting side of V.F.D
Appearances:
- The Bad Beginning (worked as the tower guard)
- The Reptile Room (posed as Dr. O. Lucafont)
- The Wide Window (posed as a ferryman)
- The Ersatz Elevator (posed as the doorman)
- The Hostile Hospital (posed as Dr. O. Lucafont)
- The Carnivorous Carnival
- The Slippery Slope
- The Grim Grotto
The Bald Man with the Long Nose
The Bald Man with the Long Nose is one of Count Olaf's associates. Described to be as bald as an egg and as devious as an Egyptian King, the Bald Man is first seen by the Baudelaire orphans in Count Olaf's house. He later helps Olaf during his scheme at Lucky Smells Lumbermill in Paltryville, posing as Foreman Flacutono. Afterwards, he poses as a head doctor at Heimlich Hospital during another of his boss' schemes. Finally, the Bald Man meets his end at the hands of several starving lions at Caligari Carnival along with the fortune teller Madame Lulu.
Appearances:
- The Bad Beginning
- The Miserable Mill (posed as Foreman Flacutono)
- The Hostile Hospital (posed as Dr. Flacutono)
- The Carnivorous Carnival
Henchperson Of Intermediate Gender
The Henchperson of Indeterminate Gender is described as being extremely fat and of unknown gender. Snicket commonly refers to them as "the overweight accomplice." It is known that they have a very strange laugh, which sounds like a howl. In The Hostile Hospital, the figure presumably met their death when in the fire that destroyed Heimlich Hospital.
Appearances:
- The Bad Beginning
- The Wide Window (posed as a security guard at "Captain Sham's Sailboat Rentals")
- The Hostile Hospital (posed as a security guard at Heimlich Hospital)
The White-Faced Women
The White-Faced Women are described by Snicket as having powder on their faces. The two sisters assisted Count Olaf in a series of crimes, such as the kidnapping of the Quagmires. In The Slippery Slope, the two become sick of Olaf's villainy and simply walk away from the group. Their current whereabouts are unknown.
Appearances:
- The Bad Beginning
- The Austere Academy (posed as cafeteria workers)
- The Hostile Hospital (posed as Heimlich Hospital's workers Dr. Tocuna and Nurse Flo)
- The Carnivorous Carnival
- The Slippery Slope
The Wart-Faced Man
The Wart-Faced Man made his first and only appearance in The Bad Beginning and is described as being important-looking. He was the member who turned off the lights in the theater so he, Olaf, and the troupe could escape. His current whereabouts are unknown.
Appearances:
Unseen associates
In The Bad Beginning, there were several other people (at least 7) invited to the dinner party at Count Olaf's house. Although the Baudelaires could not see them, they promised to be just as frightening as the other henchmen. Their current whereabouts are unknown as they are not mentioned again, except in chapter 10 of Lemony Snicket's autobiography, which contains pages from Snicket's commonplace book sent to the Valorous Farms Dairy.
Appearances:
- The Bad Beginning
- Lemony Snicket: The Unauthorized Autobiography (Mentioned in the tallying page of Olaf's associates)
Later associates
Madame Lulu
Madame Lulu was an associate introduced in The Carnivorous Carnival. She told Count Olaf where the Baudelaire children were each time they moved. It is strongly implied that she was in love with Olaf, which is likely the reason that Esmé wanted her to be pushed into the lion's pit. She was eaten by lions and fell into the lions pit along with the Bald Man with the Long Nose. Her real name is Olivia Caliban.
Appearances:
Hugo, Colette, and Kevin
Hugo, Colette, and Kevin were three freaks from Caligari Carnival who joined Count Olaf's troupe in The Carnivorous Carnival. It is unknown whether or not they survived the Hotel Denouement fire.
In The Penultimate Peril, the three of them are in disguises:
- Hugo is disguised as a worker at the rooftop sunbathing salon.
- Colette is disguised as a chemist who passes by.
- Kevin is disguised as a washerwoman by the laundry room.
Appearances:
Carmelita Spats
Carmelita Spats first appeared in The Austere Academy, but joined the Troupe in The Slippery Slope, when Esmé adopted her. She named Olaf's submarine Carmelita and performed tap-dancing ballerina fairy princess veterinarian dance recitals to torture the children rowing the ship. It is unknown whether she survived the Hotel Denouement Fire.
Appearances:
- The Austere Academy
- The Slippery Slope (Joined the Troupe)
- The Grim Grotto
- The Penultimate Peril
Fiona
Fiona joined Count Olaf's troupe briefly to stay with her brother, Fernald, and to find her stepfather, Captain Widdershins. She later double crossed Count Olaf and stole his submarine, The Carmelita. In The End, Kit Snicket says that she rejoined the Fire-Fighting Side of V.F.D. with her brother, and was either killed or saved by The Great Unknown.
Appearances:
Ernest Denouement
Count Olaf said in The Penultimate Peril that Ernest Denouement was part of his troupe.
Appearances:
Dr. Georgina Orwell
Georgina Orwell was an optometrist and a hypnotist who only appeared in The Miserable Mill. She hypnotized Klaus multiple times, using the words lucky and inordinate. Dr. Orwell was killed by the buzz saw when she stepped back into its path.
In the Netflix TV series, she was instead killed by the furnace when she accidentally stumbled backward into it. Her death was confirmed by a cracked set of glasses flying out a moment later.
Appearances:
Esmé Squalor
Esmé Squalor first appeared in The Ersatz Elevator, wherein she helped Olaf with his plans to steal the Quagmire and Baudelaire fortunes. She revealed that she knew about Count Olaf's plan all along, after pushing the children into the ersatz elevator. In The Vile Village, she becomes his girlfriend, and remains with him until The Penultimate Peril, when Count Olaf fires her. She supposedly perished in the Hotel Denouement fire.
Appearances:
- The Ersatz Elevator
- The Vile Village (posed as Officer Luciana)
- The Hostile Hospital (posed as a Heimlich Hospital doctor)
- The Carnivorous Carnival
- The Slippery Slope
- The Grim Grotto
- The Penultimate Peril
The Man With A Beard But No Hair and The Woman With Hair But No Beard
The Man With a Beard But No Hair and the Woman With Hair But No Beard are described as having "an aura of menace;" even Olaf and Esmé are afraid of the pair. It is unknown if they are members of the Fire-Starting Side of V.F.D., but they do not seem to know very much about the organization if they are. The two first appear in The Slippery Slope wherein they use V.F.D. Eagles to kidnap a group of Snow Scouts. The two later appear in The Penultimate Peril as High Court Judges for the Baudelaires' trial. It is unknown whether the two survived the Hotel Denouement Fire.
Appearances:
Other associates
Ivan Lachrymose
Lemony lists Ivan Lachrymose as an associate of Count Olaf. Ivan is only mentioned in the series.
Monday
Olaf mentions a woman named Monday and states that she is one of his associates.
Minor associates
- 1 Count[source needed]
- 3 professors[source needed]
- 1 son[source needed]
- Esmé Squalor Fan Club