@generica I wouldn't be surprised if you were proudest of those who bought their way free. I would be, too.
Some of my ancestors settled in upstate New York. AFAIK, they didn't have slaves, and one of them lost an eye fighting for the Union, but they weren't above hiring black servants.
One of my ancestors eloped with one such servant, so if racists had their way and brought back the "one drop rule", I might just pass for white. My mother probably wouldn't, though.
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@starbreaker
Your post hit home - I won't bore you with too much detail but I do genealogy as a hobby. My white ancestors owned slaves. Were some nice? Maybe. My black ancestors worked nights after the field to buy emancipation. Were some assholes? Maybe. Which ones am I most proud of? Guess.