Confronting History, Family and Race on a Road Trip to New Orleans

His hard stare meets me every morning, but now I return his gaze.

The old pirate doesn’t make me flinch anymore, the way he did when I was a boy, because I finally know who he is. I learned this by testing the truth of the family stories that I’d grown up with about Jacinto Lobrano, my great-great-grandfather and the pirate Jean Laffite’s right-hand man, during a six-day trip along the Gulf Coast.

This unsigned portrait of Jacinto Lobrano hangs in the writer’s house. Credit…via Alexander Lobrano

In my father’s family, this unsigned oil painting is passed down to the firstborn son, and now hangs on the wall of my house in a village outside of Uzès in France. Jacinto, who was born on the island of Procida in the Bay of Naples sometime during the 1790s, is depicted as a stern but handsome man in his late 40s, with wavy chestnut hair and a small gold earring in one ear. He presents as a prosperous and possibly respectable family man.

But he was still a pirate, a fact I clung to growing up in a Connecticut suburb that pasteurized difference in defense of propriety. Though my ancestry is 95 percent British Isles, being even a tiny bit descended from a pirate made me different, maybe a little glamorous and potentially wild.

As I learned the first time I read Jacinto’s obituary when I was a freshman in college, he also profited from enslaving people. This shocked me, so I called my grandmother to learn more. She was vague, suggesting he’d just dabbled in the slave trade. Her temporizing didn’t soothe my revulsion, so I did what millions of other white Americans have done when they discovered this evil in their family’s past. I dropped this knowledge like a stone into a well of denial.

Then, eight years ago, I got an Instagram message from a high school student in Mississippi named Dakota Lobrano Wallace. She’d come across me on Google and thought we might be related, and wondered if I could help fill out her family tree.