WARNING: all spoilers are unmarked.
Season 1
- The death of Frank's sister and her children.
- Rudolf Wegener visiting his children and estranged wife in Berlin, seeking to make amends with them since he knows that one way or another, he won't be coming back from his meeting with Hitler. He's holding back tears as he hugs his son and daughter, not wanting to tell them that they'll never see him again. In an especially poignant moment, he explains to his son that it's hard to be a good man, but the harder it gets, the more important it is to at least try.
Season 2
- Tagomi makes a phone call to the Wegener residence. Mrs. Wegener sobs that Rudolf is dead. Even worse considering his last visit with his family.
- Thomas being taken away to be euthanized.
Season 3
- Joe being forced at gunpoint to execute his father. Heusmann is an Asshole Victim, but this is Joe's Despair Event Horizon. The Joe Blake of the previous seasons, who wanted to be a good guy, tried to get away from Smith and the Nazis, and even at his worst was conflicted about following Smith's orders, dies when he pulls the trigger. What remains is an empty shell that barely remembers the soul it used to have.
- Frank's execution. Kido drives him to the site of a former internment camp, and after a brief conversation, he dons his full military dress uniform and gives Frank an honorable death.
Season 4
- John's flashbacks in "Mauvaise Foi." His commanding officer shows up wearing his US Army uniform but now including a swastika armband. The look on his face shows that he does not want to do this, but there is absolutely nothing he can do. And then when John turns his back on a Jewish comrade and others as they are driven off to their inevitable fate under the new regime.
- John's Despair Event Horizon and Driven to Suicide after his wife sells his location out to the resistance and finding out the infeasibility of bringing his alt!Thomas to his own world as a Replacement Goldfish. Ever since his defection to the Nazi Party since the end of World War II, and doing heinous deeds such as refusing to save his best friend from his inevitable fate and supporting the Nazi ideologies, it's hard to NOT feel sorry for him as he was doing this for the sake of his family, especially when he realises that out of the worlds he could have lived, it was this route to a downward spiral.
- Childan's separation from his wife when they tried to emigrate to Japan together, especially when his wife fruitlessly tried to give her engagement ring to the officer prohibiting Childan to get on board at one point but was forced to leave him at the end, leaving Childan seeing her ship sail off into the distance.
- That being said, he sold off his entire store full of antiques to the Yakuza in exchange for a passage to Japan on a trawler, and he ultimately gets one, but it is left for the viewer if he got there safely or not.
