- "Call me Sir. Everyone does, because I tell 'em to. I'm the boss, they have to do what I say."
- —Sir introducing himself to the Baudelaire orphans
He is portrayed by Don Johnson in the TV series.
Sir is the owner of the Lucky Smells Lumbermill, located in Paltryville. Sir's real name is unknown. It is extremely difficult to pronounce, as evidenced by Mr. Poe's attempts early in the book. Equally obscure is Sir's appearance, his entire head is hidden by a thick layer of smoke from his ever-burning cigar.
He shows little concern for either the Baudelaire orphans or his employees, whom he pays in coupons and provides an unsatisfying meal of chewing gum for lunch and disgusting casseroles for dinner. The possible reason he is so mean and greedy is that, according to Charles, he had a very terrible childhood.
It is possible he is a member of V.F.D. (probably the fire starting side).
In the book, it is left ambiguous that he may have conspired with Georgina Orwell. In the TV series, it is revealed they did conspire as he gets free labor and they split the profits, however, Sir simply thinks that Orwell simply does "weekly eye exams to boost worker morale" instead of hypnotism.
The Miserable Mill
In the end of The Miserable Mill, he fires the Baudelaires, claiming that they were too much trouble and that wherever the Baudelaires go, misfortune follows, and he will have no more of it.
In the TV series adaptation, a worker's revolt causes Sir to flee instead of stay at the lumbermill.
The Penultimate Peril
Sir and Charles relationship
It is thought by some readers that Charles is in a relationship with his boss and partner, Sir:
- Some moments in The Miserable Mill in combination with their chat in The Penultimate Peril have suggestive lines
- In The Penultimate Peril, they share a room when they travel together to the Hotel Denoument, share a relaxing sauna together there, and when the hotel is set on fire, they are holding hands as they attempt to escape.
- In The Beatrice Letters, Lemony Snicket tells Beatrice Baudelaire that he will love her until "C realizes that S is not worthy of his love," confirming suspicions of the relationship.
- They are mentioned to be partners—the lack of mention of them being business partners is unusual, and suggests they may be romantic partners.
The TV series adaptation made this relationship more explicit.
- Klaus: Doesn't "partner" mean "equal"?
- Lemony Snicket: Well, in fact, "partners" can mean several things. It could mean "two people who own a lumbermill together, or a cupcakery." Now, with the advent of more progressive cultural mores, not to mention certain High Court rulings, it could also mean...
- Sir: I do all the work. He irons my clothes.
- Charles: I also cook your omelets.
- Lemony Snicket: The definitions are not mutually exclusive.
At one point, while Violet is snooping around the library, she eavesdrops on Sir and Charles. Charles attempts to kiss Sir but Sir does not notice.
At the end of Episode 8, Violet asks what Charles plans on doing next. Charles responds that he plans on searching for Sir even though he's not a good person. He tells the Baudelaires, "Some day you will learn that some things aren't always black and white."
When asked about LGBT characters in his novels, Daniel Handler specifically mentioned Sir and Charles despite there being no prior mention:
- "I grew up in an environment of queerness of every stripe, and I'd like to believe my work reflects such a world, even if the romantic and sexual lives and preferences of many of my characters are not explicit, as they aren't in life. (After all, we don't know what Sir and Charles do when we're not around, as we don't know, and thank goodness, with many friends; my new forthcoming YA novel has already ruffled the feathers of both queer and straight readers for scenes portraying certain flexibilities.)"
- —Daniel Handler
In another interview, when Daniel was asked about who is LGBT in A Series of Unfortunate Events, he replied he wanted to leave it up to speculation, but said, "More than you probably think, as in real life."(25:00)
- Charles' duties involve ironing Sir's shirts, cooking him omelettes, and making him milkshakes.
- Sir wrote the book The History of Lucky Smells Lumbermill and donated it to the library. One of the sections is "Sir a Legend in the Making".