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* The death of Nelson van Alden. After years of living lies, being forced into circumstances beyond his control, his moral failings and ultimately growing distant from his family as a mobster under Al Capone, van Alden realizes it's only a matter of time before Capone turns on him. When his and Eli's plan fails, van Alden realizes that Capone will kill him and goes out on his own terms: overpowering both Al and Ralph Capone and throttling the former, embracing his true name and putting the fear of death into the most powerful man in Chicago before being shot dead. It still leaves Eli horrified and shows a reminder than van Alden had it in him to be a much better human being than he became.
* Eli's own pain. Van Alden's wife Sigrid reveals that they had sex to Eli's devoted wife June. From Eli's recollections, it's more than Sigrid raped him after getting him too drunk to consent. Eli sends the series separated from June and his kids, with Nucky's last ever meeting with his brother being to encourage him to try to make amends. After all the pain, betrayal, and a lifetime of complicated ill-will, the Thompson brothers part with a last brotherly embrace and Nucky leaving Eli enough money for a lifetime- and a shaving razor to be presentable when he goes to see June again.
* Eli's own pain. Van Alden's wife Sigrid reveals that they had sex to Eli's devoted wife June. From Eli's recollections, it's more than Sigrid raped him after getting him too drunk to consent. Eli sends the series separated from June and his kids, with Nucky's last ever meeting with his brother being to encourage him to try to make amends. After all the pain, betrayal, and a lifetime of complicated ill-will, the Thompson brothers part with a last brotherly embrace and Nucky leaving Eli enough money for a lifetime- and a shaving razor to be presentable when he goes to see June again.
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* For the first time we see Rothstein have a genuine weakness: he's a gambling addict and can't stop even when his poker game is going badly. Lansky has to intervene to pull Rothstein out before he loses more and when the victor smugly mangles the Jewish Rothstein's name, the normally unflappable A.R. seems genuinely hurt. He can only softly correct the man as to his name with as much dignity as he can muster before shuffling out. It's a painful reminder that to some people, Rothstein will never be anything more than a Jew. And this time, unlike with Rosetti or Masseria, he's being reminded from a position of loss.
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** Also the way that, upon Jimmy's return home, Richard promptly scrambles to put his mask back on. Despite having spent want has to be hours without it on whilst being sketched, as soon as someone - even his closest friend in the world - shows up, he absolutely ''has'' to have it back on. The amount of shame he must feel at his appearance, that he can't even be unmasked around Jimmy, is heartbreaking.
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** Also the way that, upon Jimmy's return home, Richard promptly scrambles to put his mask back on. Despite having spent want what has to be hours without it on whilst being sketched, as soon as someone - even his closest friend in the world - shows up, he absolutely ''has'' to have it back on. The amount of shame he must feel at his appearance, that he can't even be unmasked around Jimmy, is heartbreaking.
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** Also the way that, upon Jimmy's return home, Richard promptly scrambles to put his mask back on. Despite having spent want has to be hours without it on whilst being sketched, as soon as someone - even his closest friend in the world - shows up, he absolutely ''has'' to have it back on. The amount of shame he must feel at his appearance, that he can't even be unmasked around Jimmy, is heartbreaking.
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* After a botched assassination attempt on [[spoiler:Narcisse]], [[spoiler:Richard]] is mortally wounded and dies while hiding under the boardwalk, in the same spot where he first made love to his wife. His dying dream is [[spoiler:being reunited with Emma, Tommy and Julia, with his original, unscarred face.]]
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* After a botched assassination attempt on [[spoiler:Narcisse]], [[spoiler:Richard]] is mortally wounded and dies while hiding under the boardwalk, in the same spot where he first made love to his wife. His dying dream is [[spoiler:being reunited with Emma, Tommy and Julia, with his original, unscarred face.]]]] To rub salt into the wound, in botching the assassination he accidentally killed Chalky White's daughter, after it is established he was friends with Chalky and helped tend to a gun shot wound he received from Narcisse earlier in the season.
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* After a botched assassination attempt on [[spoiler:Narcisse]], [[spoiler:Richard]] is mortally wounded and dies while hiding under the boardwalk. His dying dream is [[spoiler:being reunited with Emma, Tommy and Julia, with his original, unscarred face.]]
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* After a botched assassination attempt on [[spoiler:Narcisse]], [[spoiler:Richard]] is mortally wounded and dies while hiding under the boardwalk.boardwalk, in the same spot where he first made love to his wife. His dying dream is [[spoiler:being reunited with Emma, Tommy and Julia, with his original, unscarred face.]]
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* Chalky's reaction to [[spoiler: his daughter's death]]. Damn Williams deserves at least an emmy nomination for it
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* Chalky's reaction to [[spoiler: his daughter's death]]. Damn Williams deserves at least an emmy nomination for it
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*** [[spoiler: It was about more than revenge. Consider Tommy's words to Nucky, "That's your answer to everything." And then remember Nucky's last visit with Gillian.]]
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*** [[spoiler: It was about more than revenge. Consider Tommy's words to Nucky, "That's your answer to everything." And then remember Nucky's last visit with Gillian.]]
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*** [[spoiler: It was about more than revenge. Consider Tommy's words to Nucky, "That's your answer to everything." And then remember Nucky's last visit with Gillian.]]
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** Nucky selling Gillian and his soul to get ahead.
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** Nucky selling Gillian and his soul to get ahead. The worst part is when she gives him this gaze of absolute trust and you know she has no idea what the Commodore is going to want with her.
