Watching Will and Diane’s relationship crash and burn. You just have to cringe.
For that matter, watching the relationships between Alicia and Will, Cary and Diane, Cary/Alicia and the firm, and just about every other relationship on the show just explode one after another in the beginning of season five.
Diane breaking into tears when she realises her dream of becoming a judge probably just got squashed.
Will as he makes the decision tree in ‘The Decision Tree’. The look on his face as he makes his set of questions for Alicia, and the resulting fantasy/flashback, is heartbreaking.
In a Ripped from the Headlines bit, Elsbeth is called several nasty slurs by a street performer she was enjoying. It’s strangely jarring and upsetting to see our beloved Cloud Cuckoolander be so completely stunned and hurt.
Elsbeth: (Almost in tears) I am not a dirty, stinking Jew!
Everything about the last act of ‘Dramatics, Your Honor’:
When Diane hears the gunshots, her first reaction is fearful concern to find Will.
Kalinda seeing the shoe on the ground and putting it together before pushing past security to get to her dying boss and choking out a sob once she does.
The first person Kalinda and Diane think to call about Will’s death? Even after all that’s happened, they know it has to be Alicia.
Kalinda and Diane breaking down over Will’s body.
Eli’s reaction to Kalinda’s call, and his gentle way of pulling Alicia aside and giving her privacy to hear that Will has died.
Following ‘Dramatics, Your Honor’, the entirety of ‘The Last Call,’ as everyone reacts to Will’s death.
The saddest are probably Diane, Alicia, and Kalinda’s reactions, but David Lee crying is surprisingly poignant and humanizing.
6x02 "Trust Issues" has Diane leaving her office at Lockhart-Gardner for the last time. She looks out the window, waits for five o'clock, takes a long look around, then picks up her photo of her and Hilary Clinton and walks to the elevator. As she gets in with those leaving with her, she lets out a quiet 'goodbye' to the firm that she helped establish and the last physical tie to Will, her best friend.
When Cary, Alicia, Diane, and company take back the LG offices, it is Alicia who ends up in Will's old office. The undercurrent of lingering grief that passes over her face as she walks in is heartbreaking.
6x10 ‘The Trial’ has Cary taking the plea bargain, pleading guilty to the conspiracy charges for two years in prison.