- "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.
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.
The Penultimate Peril
Sir and Charles Relationship
It is thought by some readers that Sir is in a relationship with his employee and partner, Charles. Some moments in The Miserable Mill in combination with their chat in The Penultimate Peril and them holding hands while running through the smoke of the Hotel Denouement fire hint that this theory may be true. Also, 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. As well as that, 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, referring to their partnership as one made possible by a more progressive culture and high court decisions, a reference to real-life cases such as Obergefell v. Hodges, or perhaps Lawrence v. Texas, and at one point 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."