In TMM Charles says that Sir is crabby because he had a "terrible childhood" Perhaps this is somehow connected to VFD? Perhaps he is the third White Powdered Ladies Sibling? Perhaps he is some random on the family tree, as we don't know his real name. That name is kinda fishy. It's meant to be funny, but perhaps there is something sinister behind it. IS he a long lost sibling? Is he just a random with a terrible childhood? Did his house burn down, killing his parents and leaving him alone in the world, which has hardened him and made him cruel? Who knows. You might, and if you do, please discuss it here.
Here's a weird possibility to consider: His youth somehow involved a deadly fire--perhaps his parents or siblings died in one. Because of this, he developed a sick obsession with smoke and now smokes all the time, continuously. Or perhaps his face was scarred from the fire and he uses the smoke to hide his deformity.
I think that he was treated cruelly as a child, and so is now taking it out on the world in the same way. And he probably just smokes cigars to indicate authority (I have a friend who says that he won't smoke unless he becomes head of a big company, in which case he'll smoke expensive cigars).
He's not completely alone in the world, as many of his cousins live in the dormitory of the mill (page 137, in case it matters). Although admittedly, cousins do not necessarily count.
I wonder how Charles knows he had a terrible childhood? Perhaps they knew each other as children. One thing that crossed my mind momentarily reading the book was that maybe Sir was in V.F.D. and his terrible childhood occured because of something to do with the organization. Not sure I believe it, but it's a theory. Is Sir a volunteer? Do we know? At least his mill provided the lumber for some of the volunteers' homes.
I go to bed early and rise late and feel as if I have hardly slept, probably because I have been reading almost the entire time
I think Sir providing "emerald lumber" for volunteer homes and headquarters to be the limit of his association with V.F.D. Of course, there's so little information on him that you really couldn't prove it either way.
Do we really know that Sir had a hard childhood? Charles says so, probably because Sir told him so.
In the Dickens novel "Hard Times" there is a factory owner named Mr. Bounderby who constantly tells people he had a hard childhood and brought himself up by his own bootstraps. Later, his mother appears on the scene and reveals there was not a word of truth in it; he had a privileged childhood.
It could be the same with Sir. He seems to have little feeling for the sufferings of others. It may be that he never suffered much himself.
The autobio index mentions "Opportune Odors Horseradish Factory" and refers us to one of the pages bearing the map. Hence, we can infer that the factory near Lousy Lane is called that. I also noticed the Lucky Smells connection.