WARNING: Spoilers are unmarked.
Season 1
- John LaBlonde's suicide in "Chapter Four." He was a kid who wanted a prestigious award, but unfortunately, Steven adamantly refused to give him a recommendation for it because he was a member of the soccer team who cheated on a civics test (John himself knew what was going on but didn't participate in the scandal; however, Steven felt he should've reported his teammates). The real kicker comes when John's parents tell Steven "You know why this happened" after Steven arrives at the hospital upon receiving word of John's suicide.
- "Chapter Six" had Tim McMahon, a teacher who was a close personal friend of Steven's, die of a heart attack. Steven spends the rest of the episode struggling to deal with the loss of his friend; at one point, he ends up lashing out at Marla for praying with students on school grounds. The episode ends with Steven visiting Tim's body at the morgue, and he reminisces about their first day as teachers, breaking down as he goes on, before finishing with "Go with God, my friend" and sliding the body back into the drawer.Steven: Sorry it took so long for me to come. Things have been busy. You left some people behind. I hope you know that. I remember when we started together. You were always creating trouble. You caused it right to the end, didn't you? [sighs] Did you see all those kids turn out for you today? I, uh... [starting to cry] I wish I knew you were ill, Tim. And I hope you know I loved you. Goodbye, my friend. Go with God.
- Steven and Guber's arguments in the crossover with The Practice, with Steven taking Guber to task for making major decisions without his input and Guber resenting doing Steven's "dirty work" because, in his view, Steven is too soft on employees who happen to be his friends. It's a good thing they reconcile by the end.
- Also Kevin's speech to Steven when the latter tries to smooth things out between them after Steven gives the closing statement in which he denounces Kevin as untrustworthy due to prioritizing his friendship with Milton over his duty as a teacher.
- Harry sitting in a stairwell crying after learning that Tyronn Anderson, a student he tried to protect, was fatally wounded while trying to leave town.
- Steven learns that Harry knew Tyronn murdered a rival gang member and kept quiet about the whole thing, and he confronts Harry and REALLY tears into him. Harry attempts to justify his actions and laments how he's been tormented by the likelihood that Tyronn was killed because he didn't speak up sooner, and how everything is falling apart for him. Steven, however, remains unsympathetic and implies to Harry he's definitely thinking about firing him (in the end, he doesn't).
Season 2
- Harry finds out that Jamaal bought his college application essay off the Internet and harshly confronts him about it, ending with him telling Jamal to "Get out" and Jamal walking out, crying. Jamal later begs Harry to not give up on him, but Harry remains angry. Although he does convince Williams College to give Jamal a second chance to apply, Harry coldly makes it clear to Jamal that he is not going to ever stick up for him ever again.
- In one episode, a car accident claims the lives of a group of teenagers, a few of whom attended Winslow High. A grieving Ronnie, who was close with one of the kids, bashes over the dearly departed student's chair in a fit of anger and storms out. To make things worse, she's next seen being reprimanded by Guber for acting out in front of her students, and Guber, clearly having firm hold on the Jerkass Ball, coldly tells her to "Cry at night."
- The whole season finale is basically a tearjerker.
- Ronnie going down to the Dungeon and finding Harry after Jamaal's brother had stabbed him.
- All the other staff showing up at the hospital waiting to hear news on Harry's condition.
- Steven staying at Harry's bedside and crying over his friend.
- Harvey coming to the hospital and visiting Harry and saying a Hebrew prayer for him.
Season 3
- Danny admitting to Steven that he was molested as a child by the same priest who's been molesting a Winslow High student.Steven: [sympathetically] Wounds heal, Danny.Danny: Not this wound.
- The episode ends with Danny sitting alone in a church, crying.
- In the penultimate episode of Season 3, Steven and Guber's very heated argument about the prospective budget cuts that could potentially destroy Winslow High. It starts with Guber perceiving Steven's willingness to eliminate the Dungeon as a personal attack leveled against him, and Steven in turn calls him out for his self-centered attitude and his "self-esteem issues." The two then give voice to issues that have been brewing for a long while, and Steven chastises Guber for undermining his efforts to save the school by telling Lipschitz about the budget cuts and causing all the other teachers to be afraid.
- In the same episode, Daryl, a Dungeon student that Guber had taken a shine to, is murdered in a shootout, and Guber decides to hand in his resignation, stating he can't do it anymore (by the next episode, he's back in the game).
Season 4
- In one episode, Steven's speech to the entire school about the blight of racism in society after two Middle Eastern students are taken out of Winslow High by their father due to threats, taunts, and assaults leveled against them. He starts out calmly, but gradually becomes more angered and distressed to the point where he can't even finish the speech and instead walks off, ending the episode. You can watch it here
.Steven: Ladies and gentlemen, we're living in a time...a time of...uncertainty, of fear...we're living in a time when we need to protect ourselves from harm, from attack...from terrorism. And I hate it. I hate for my loved ones, and I hate it for all of you. Now, we can't change the facts. We live in a time when our civil liberties are being compromised. But I will not run a school that tolerates hatred. I will not run a school that tolerates prejudice. And most of all, I will not run a school where parents feel they have to pull their children out of this school to keep them safe. I will not! So if any of you out here this week passed by Khalid or Sabeen Mubarik, and made a comment, or held a suspicious look, or tagged a locker, or threw a bottle, let me say this to you—Khalid and Sabeen Mubarik are you. They are you! All of you. Now I don't care if you're white, African American, Latino, Native American, Irish, Italian, Japanese, Jewish, whatever—they are you! And in their absence, we are less. Khalid and Sabeen Mubarik were not terrorists. But all this past week, we all were. We have to be better, people. We have to be better, all of us. I demand it of you, I demand it of myself... [is unable to go on, so he walks off] - In "Chapter Eighty," Steven reading a letter sent to him by Billy Deegan, a former student who was killed while serving in Iraq, and saying a tearful "Goodbye, son."
