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Source: https://writers.stackexchange.com/q/38243
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

Now, to clarify ahead of time; I'm quite aware that compelling doesn't necessary equal sympathetic and vice versa. That being said, here is the dilemma.

There's a character that I intend to write who is an antihero, both in the classical Greek sense (highly flawed and not always successful in his endeavours) and in the modern sense (morally ambiguous). Despite this, I'd prefer that the readers of my novel retain sympathy for this man; not necessarily want him to attain his goals, but at the very least hope that he's okay by the end of the story.

However, one key trait that he has which, while it makes sense in-universe, would alienate a standard modern reader pretty quickly. His day-job involves information gathering and retention, a kind of historian/scholar/spymaster hybrid, and while the story isn't _about_ his day-job, he has a clear history of torturing people (and commanding his underlings to do the same).

It's clear he doesn't derive pleasure from this, and occasionally he's tormented by his memories of his attempts to train a torture-master to essentially 'take the blood off his hands'. Despite this, throughout the story, he doesn't come to _regret_ having to torture people (though he does acknowledge the mental hoops he has to jump through to make torturing a man acceptable at all).

In-universe, this makes sense; he's just doing his job, and while he wrestles with the terrible side of it, ultimately he can't afford to angst about it every moment when his employers will need him for it just as much after the story as they will before it. He's not defined by his ability to torture people, it's just part of a skillset in his line of work.

Out-of-universe, however, I'd say the average reader might not be too inclined to root for a mostly unrepentant torturer, regardless of his motives and context, just as one isn't inclined to sympathise with an Auschwitz guard. He's not some vigilante performing 'just torture' (though I don't think any form of torture is just, but that's a moral quandary that's neither here nor there), it's just... a facet of his life.

His ultimate arc involves him learning to become a leader in his search for a missing child, and if anything, he learns to _stop_ apologising for his morally questionable actions rather than becoming _more_ regretful. His arc is about growing a sense of resolve in spite of acknowledging his flawed nature.

My question is thus:

What lines can a character cross while maintaining a reader's sympathy in the modern age?

Ideas that I have on the topic:

- Clarifying a lack of malice behind a character's actions _neutralises_ a character's unsavoury qualities, but doesn't necessarily endear a person to them.
- Having the character angst over their own 'monstrosity' _can_ endear a reader, but can just as easily clash with the setting and/or become tedious to a reader with a low tolerance for melodrama.
- A sympathetic goal is oftentimes more important than the person pursuing them.

What are you guys' thoughts on the matter?

Original score: 11