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* Yassen's speech to Alex to [[IJustWantToBeNormal try and be normal]] at the end of Book One, to not let [=MI6=] use him. And then he gets shot by Damian Cray after refusing to kill Alex and Sabina in ''Eagle Strike''. The guy doesn't get a break where his MoralityPet is concerned.
** This is worse in the film adaptation. Yassen goes out of his way to save Alex's life in public and then drops him off to safety. Alex wants to kill him, but he just tells him to get out. Knowing what's going to happen to Alex in the series makes it [[HarsherInHindsight heartbreaking]].
--->'''Yassen:''' You don't belong to the same world as me.
* CIA Agents Troy and Carver getting ImpaledWithExtremePrejudice by a DurableDeathtrap while exploring a hidden entrance into Sarov's island. Alex has to piece together what's happened, and he barely has time to process it before having to fight off a shark and getting drugged by Sarov's men.
** What's worst is that they're all posing as a family, and while they're pretending Alex wonders what it would be like if it were the real thing.
** Troy gets a moment where she admits she's being a {{Jerkass}} to Alex is because he's the same age as her nephews, and it freaks her out that someone as young as him is in the field.
* General Sarov's suicide at the end of ''Skeleton Key.'' All he wanted was for Alex to be his son. Denied that (and on another level, his master plan), [[DrivenToSuicide he kills himself rather than Alex,]] [[DespairEventHorizon as he has nothing left to live for.]]
* Jack's death. It doesn't help that the point of view directly before it happens is switched to Jack's, describing her attempted getaway, giving the reader some hope that she might actually succeed. Alex's reaction made it even more heartbreaking, because this is the first time we actually see him outright lose his cool - and the first time we even see him cry, for that matter. Hell, he actually blacks out as a result of his grief. It shows how much she really meant to him, and how much her presence kept him together. Strengthened by the fact that it was also a NeverGotToSayGoodbye moment and was done ''solely'' to torture Alex emotionally.
** And then at the end, when Razim is dead, Alex is found kneeling by the exploded car she died in...
* Alex calling out for Mrs Jones when he's been shot at the end of ''Scorpia''.
* Alex being told the truth about his parents at the end of ''Scorpia''. It is one of the few times Alan Blunt ever displays emotion of any kind, there being audible pain in his voice towards the end, and the only time he actually tries to comfort anyone:
-->"Your parents died together, Alex. I suppose that's something of a mercy. And it would all have been so quick. They wouldn't have had any idea..."