This is based on opinion. Please don't list it on a work's trope example list.
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Season 2
- "Break Point": Louis' cat Bruno dying and ending up to be euthanized. While it did occured off-screen, it doesn't make it any less heartbreaking and anyone who has or had a cat will understand why he looks like his world has crashed. Also, Donna getting fired. The look on her face is just heartbreaking. Even though we know she'll end up coming back one way or another, it's still heartbreaking.
- "Asterisk": Mike's grandma died. His face when Rachel tells him is just devastating. Doubly so because he was finally making enough money to be able to properly take care of her and was happily preparing the apartment he bought for her when Rachel comes to see him.
Season 3
- When Louis tries to befriend Mike in "I Want You to Want Me", after Harvey had been an unforgiving jerk to him since the season 2 finale, with Harvey's blessing. By the episode's end, Harvey forgives Mike and Mike goes back to Harvey at the first opportunity... after he just told Louis he would join him. You can just see Louis's heart breaking as he walks up holding a chocolate cake, which he ends up throwing away. It had "Welcome to Team Litt" written on it. Sniffle.
Season 4
- Louis... just Louis in the scene in "Leveraged" where he tells Harvey that Mike getting Forstman to fund his plan because of something that Louis told him, when he went to stick it to him. The conversation is heartbreaking and Louis is nearly in tears:
Harvey: Goddamn it, Louis. I don't wanna keep being mad at you, but you keep doing the same sh*t.
Louis: But you see, this wasn't me being duped.
Harvey: No. It was you letting your emotions lead you into doing something stupid Again. You just had to stick it in his face. You know what? I'm done.
Louis: (visibly holding back tears) It's not fair, you know. I'm emotional. You're cold. You're loved. And I'm hated.
- Happens again to Louis. To be the hero, he had to break the law. The law comes biting back and the only way to save himself would be to frame Harvey. While Louis can be slimy, he's not that slimy yet of course going to prison for a fairly significant felony and destroying his life is obviously not the most thrilling option either.
- The flashback to young Michael coming down the stairs to find his grandma waiting to break the news of his parents dying in a car crash.
Season 5
- The entire episode of "Faith", culminating in this conversation:
Mike: Harvey, you didn't just give me my dream. You gave me a family. But I'm gonna have a family of my own someday, and I can't have all of this hanging over their heads.
Harvey: You're resigning.
Mike: I am.
Harvey: You know, you once asked me why I hired you, and I told you it was because life is like this and I like this.
Mike: Harvey, please, you can't convince me—
Harvey: Let me finish. It was like this not because of the risk we're taking. It's because of who you are.
Mike: So you're not disappointed?
Harvey: Are you kidding me? After that speech, if you hadn't done this, I'd be kicking you out. And for the record, you're not the only one who got more family out of this deal.
- "25th Hour" is full of these, but a special mention has to go out to the revelation that the verdict about Mike would have been not guilty.
- Sean Cahill is usually shown as a major Jerkass, a cold federal agent ready to screw anyone over to get the job done. In "Spain", he shows up at Harvey's office and, showing true humanity, reveals why he wants Sutter taken down so badly. Cahill's mother had been a teacher all her life, hard-working and always dreamed of a trip to Spain when she retired. But just as she was about to, the teacher's union invested in one of Sutter's funds which led to it being bankrupted. Cahill offered to pay for his mom's trip but she refused, wanting to pay on her own. So she kept on working until her death just a year earlier, having never seen Spain and Cahill wants payback for Sutter ruining his mom's dream.
- Mike gets a temporary job teaching at his old Catholic high school and learns it's a pack of punks who mock him on his jail time. The next day, Mike coldly snaps at them on how the beloved older teacher he's filling in for is dying of cancer. They're truly shocked with the leader of the group sadly sharing the story of the man's fondness for fishing and all of them bonding.
- Which becomes sadder when the head priest tells Mike that the parents don't want an ex-con teaching their kids. Mike understands and tells him to say goodbye to the kids for him.
- After showing off "The Donna" to potential investors, Donna sneaks back to overhear what they really think. She hears them all right...as they talk about how they only took the meeting because Harvey asked them to and "no way I'm getting into business with a legal secretary." Donna keeps a straight face but clearly rocked by how easily she's dismissed.
- In "Character and Fitness" when Tara breaks up with Louis over voicemail. Louis is devastated and breaks down. Doubles as a moment of heartwarming as Rachel puts her arms around Louis and comforts him.
- The simple, brutal truth Jessica brings to Harvey after she's disbarred for covering up Mike's fraud so long.
Harvey: We can't have the name on the firm of a partner who's been disbarred!
Jessica: Why do you think I came here?
- Harvey's mother passing away, just as they were finally in a good place after years of estrangement.
