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Most emotional trauma/angst?

F. King Daniel

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Curious who goes through the worst time in Treklit? Quark and Rom went through an horrific time in The 34th Rule, Brenna Covington never knew a moment of joy in Homecoming/The Farther Shore. Are there any others? What's the worst stuff to happen to the TOS crew since not a lot is coming to mind?
 
The Meta, from Peter David's The Seige, copped a pretty nasty ending. Being self aware forever in millions and millions of little pieces scattered throughout the Gamma Quadrant can't be good for your mental health!!!
 
Kirk's knee injury in a flashback in Crisis on Centaurus sounded really painful.

Yet his knee injury plus the aftermath of Ghioghe in E:TFA left him with nightmares.

Spock's head gets dented in, in Mindshadow.

Honorable mention to Cleante and T'Shael in Dwellers in the Crucible for their ordeal, though they aren't Enterprise crew.
 
Karatek from the Vulcan's Soul trilogy also suffered a ton, with the whole exile from Vulcan thing, being duped into becoming a slave on Remus and losing everyone around him like three times over.
 
Iliana Ghemor really gets put through the wringer in Fearful Symmetry.

After her childhood sweetheart gets killed in a terrorist attack on Bajor, she begrudgingly joins the Obsidian Order. During her training, she is deceived into killing someone in what she thought was a training simulation. Then, after she gets assigned a mission to infiltrate the Bajoran resistance and undergoes a surgical procedure to assume the identity of Kira Nerys, Dukat takes her captive and forces her into slavery for years. When she finally manages to escape at the tail end of the Dominion War, she regains her memories as Iliana, but retains her memories of her undercover identity as well; the two warring identities drive her mad.

Pretty dark stuff.
 
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0 in the Q Continuum trilogy. Spoilerific details below (read the trilogy first, it's ace)

banished outside the galactic barrier twice(which was specifically created to keep him out), only able to travel at impulse speed iirc
 
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