Are there any slave-owning characters in the fiction of the last 50 years or so who are depicted as being sympathetic?
There’s technically Dr. King Schultz in Django Unchained.
(I said “technically”.)
Does Luke Skywalker’s family owning droids count?
In Rome, Vorenus was a sympathetic character, as were a bunch of upper class Romans (Caesar, Octavian, Cicero, Marcus Antonius, etc), all of whom were slaveholders.
Is he technically sympathetic, technically a slave owner, or technically both?
The TV show Game Of Thrones(and the book series it is based on) have as a major plot point a conqueror taking over cities and freeing the slaves that live there.
It has not tried to show any slave owners in a sympathetic light, and none are real characters, likely because it is too hard. I don’t know if the book series goes into more detail.
*Duplicate post sorry.
He is sympathetic, and technically a slave owner although he is actually helping the slave he owns rescue his wife but he isn’t totally altruistic either. From IMDB:
It’s a stretch but in the Harry Potter universe, Sirius Black “owned” Kreacher, though neither of them seemed particularly happy about the arrangement.
It’s easier to make a slave-owning character sympathetic when the slave ownership is not central to the character or his or her occupation. It isn’t as though Sirius was a magical plantation owner or something.
Marcus (Channing Tatum), in The Eagle, owns the slave Esca (Jamie Bell) for much of the movie and is the hero. Don’t know if that relationship is in the source material, AFAICT Esca’s already freed in that.
Not exactly the right answer, but in the movie “The Patriot”, Mel Gibson played Benjamin Martin, a Real - Life slave owner, but I seem to remember that in the movie they pretend that the slaves are free workers.
Which reminds me of 300, where famously brutal enslavers the Spartans are portrayed as hating the concept of slavery and the real life slaves that fought in the Thermopylae erased from existence.
Of course there are also plenty of movies with Thomas Jefferson, including movies portraying his relationship with Sally Hemmings.
And more or less any movie or TV show about ancient history, of course. I’d say Rome, but it’s hard to tell if one could consider Vorenus and Pullo to be all that sympathetic.
I know the book well. Much of the story in the book occurs before they go North, and it’s only when about to set out on the journey that Marcus frees Esca and asks if he is still willing to come as a friend rather than a slave. Esca responds, in effect, the service he has been giving Marcus has – latterly at least – been from the heart and not as a slave, and he is more than willing to go.
Marcus is a sympathetic owner who allows Esca some liberty, including going on a hunting trip that he, Marcus, is not physically fit enough for. His uncle owns a number of other house slaves who are never seen as other than content with their lot, and in some cases actively prefer not to be free. Of course, this is something apart from 19th-century chattel slavery and it is remarkable but not unheard-of for Esca to be freed.
Almost any book set in Ancient Rome or Greece. Unless you were in poverty, or a slave yourself, the question was more “how well do you treat the slaves you have” rather than “will you have slaves”
And after Sirius died, Harry became Kreacher’s owner. So that’s another sympathetic slave owner.
I dunno; by Book 5, Angry Jackass Harry™ was pretty much in full swing, and getting less and less of my sympathy. 
The slave owner played by Benedict Cumberbatch in 12 Years a Slave was certainly more sympathetic than the brutal Michael Fassbender character he sells Chiwetel Ejiofor to, and is shown as trying to be kind to his slaves. He rewards the Ejiofor character for his good work with the gift of a violin, which Ejiofor is later able to use to earn some money on the side.
Ultimately money is more important to the Cumberbatch character than the well-being (or freedom) of the slaves, though. When Ejiofor tells him that he’s a free man who was kidnapped, Cumberbatch doesn’t so much disbelieve him as refuse to listen.
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Ultimately money is more important to the Cumberbatch character than the well-being (or freedom) of the slaves, though. When Ejiofor tells him that he’s a free man who was kidnapped, Cumberbatch doesn’t so much disbelieve him as refuse to listen.
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His wife’s comment to the woman who has been sold away from her children was chilling- paraphrasing, but something like “Some rest and some good food and you’ll soon forget all about them”.
The final master in ROOTS is shown as a likable character. For that matter, Tom Lea (or Murray in the miniseries) is not sympathetic but he’s not one-dimensional; he rapes Kizzy and fathers Chicken George, but has genuine love for his son and grandchildren.
The Benjamin January books by Barbara Hambly have some at least semi-sympathetic slave owners. She does a good job, I think, in having a full range of characters, from monsters to people you would expect to like if you met them.
I haven’t seen Hell on Wheels, but isn’t the main character a former slave owner? I assume he’s intended to be sympathetic?
No, he had free blacks who worked for him.
Major cop-out: Mississippi had one of the smallest free black populations in the U.S. and it was notoriously difficult for free blacks to stay, let alone work as free laborers on a farm. This is a step ahead of him having a bunch of black buddies who sometimes dropped by to work in his fields, but it’s basically sidestepping the PC minefield of making a slaveholder at all the good guy.