Short story (or maybe a small book) about two students kidnapping a teacher

Question

I think I read this in elementary school, so it was probably late 1980s to early 1990s (I was in elementary school between 1985 and 1992) in Ashland, KY. I don't think it was illustrated, or if it was, it was just a few sparse pen-and-ink drawings to set the scene. The basic plotline is that the male protagonist, somewhere in middle school to high high school, falls in with another male around the same age. This male is implied to be from a well-to-do family, but largely unattended. I remember a scene where they were sitting in the living room by a fire, drinking something from glasses (probably alcohol) and the rich boy punctuates his point by hurling his glass into the fire, inspiring the other boy to do the same.

The two of them shared a mutual dislike for a male teacher, I think with bushy eyebrows, who had a name like "Mr. Gulag" because they made a joke about "Mr. Gulag's gulag" in regards to detention. Anyhow, they decide to kidnap him, maybe just to put a scare in him, maybe to do something more nefarious. I don't remember many of the details... I think they ambush him in the parking lot with a chloroform-soaked rag. Wherever it is they take him, they have him tied up with rough ropes. After that, all I remember is that the rich boy is getting out of control, suggesting more criminal acts to do as "revenge" against this teacher who's far too tough on him, while the main protagonist realizes just how far in over their heads they are and tries to talk him down. The teacher manages to get them conversing and eventually convinces them to let him free in exchange for him not turning them in, or maybe for pleading clemency.

I don't remember a lot of the characters. Either they were all Caucasian or not enough fuss was made about their race to make it worth noting. I want to say that the richer boy was dark-haired and that the teacher was grey-haired with bushy eyebrows. The part which has stuck with me so much was that his name sounded like "gulag".

Answer 1

Gruel and Unusual Punishment by Jim Arter

Merry prankster Arnold Dinklighter admits that he detests Mr. Applin, the supervisor of detention--a place where Arnold spends most of his time--but is not sure he likes the joke his pal Eddie wants to play on Applin: to kill him.

Mr. Applin's detention room is known as "The Gulag."

The Kirkus review:

In a bitter tale about misfits out to get a hated teacher, Arnold Dinklighter, repeating seventh grade, spends most of his time suspended from school, cooking up annoying pranks, being paddled by the principal, harassing classmates, or in detention, supervised by history teacher "Apeface" Applin. Unlit by any spark of generosity or kindness, Arnold despises everything and everybody ("The last time there was any color to your marriage was when your eyes were black and Dad's nose was red," he says playfully to his bleary, incompetent mother), but he finds a companion in new student Edward Straight, whose hostility and uncontrollable temper make him an instant discipline problem. The two agree that Applin must suffer, though Edward's talk of "taking him out" does make Arnold uneasy. Though title, names, and other cues suggest a comedy, there's little here that's funny and Arnold's too unlikable to get much sympathy. In a soapy denoument, Arnold saves Applin from Edward's knife attack, then takes the teacher to meet his mother; she announces that she has another son, institutionalized since infancy, and Applin suggests that she seek counseling--a suitably inane conclusion to this weak first novel.~(Fiction. 11-14)

This can be the glass scene you remember:

"Well, you can count on me, thick or thin." "I imagine you'll be rather thick." "This will be great," Edward said, talking quickly. "We're going to take care of the Apeface. That stupid idiot Apeface." Edward laughed wildly, took a final drink of his pop, and threw the glass across the pool and against the fence. I was surprised by the suddenness of it and the sound of the shattering glass. I was just as surprised when Edward looked at me and nodded with a strange gleam in his eye. I shrugged.

Gruel and Unusual Punishment (1993) by Jim Arter, on Google Books.