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.
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.
It seemed likely that we had ancestors in common, since the pirate had five sons and two daughters, but I didn’t know how. And it didn’t entirely surprise me when I saw Dakota was African American. In New Orleans, where Jacinto Lobrano and his sons had lived, sexual relations between the races were common, often initiated by white men who forced themselves on enslaved women.
I told Dakota I’d be happy to share what I knew, but warned that it would obviously be ugly. “I’m OK with that,” she replied. I sent her everything I had, including the Nov. 12, 1880, obituary of our forebear from the New Orleans Picayune.
We became friendly via occasional messages about her high school graduation, subsequent nursing school studies and my work, our immediate families and politics, and we eventually began addressing each other as “Cuz.”
According to his obituary, Jacinto and his father had left Italy because they’d been involved in a plot against the government. Eventually, they’d ended up in the Gulf of Mexico, where Jacinto fell in with the French pirate, Laffite. Jacinto was instrumental in persuading Laffite to side with the Americans during the War of 1812. Jacinto then fought so bravely during the Battle of New Orleans that Gen. Andrew Jackson presented him with a silver sword. The story passed down in my family was that when Union troops occupied New Orleans in 1862, the old pirate sent a note to the invading Maj. Gen. Benjamin Butler threatening to use his most prized possession to remove his Yankee ears if anyone attempted to confiscate it.
Jacinto lived in a large house at the corner of Laurel and Fourth Street and engaged in a variety of different businesses, including buying and selling enslaved people.
I wrote to Dakota to see if we could meet if I came to Mississippi. When she agreed, I planned a trip along the Gulf Coast, starting in Sarasota, Fla., where I owned an apartment, with stops in Pensacola, Fla.; Ocean Springs, Miss.; and one to see Dakota in Hattiesburg, Miss., where she was working on a graduate degree in health care; and then continuing to New Orleans where I would visit another cousin.
A Date in Hattiesburg
So often we travel to find out who we really are and to make ourselves better with this knowing. I traveled to the American South to meet my lovely cousin in Mississippi. In ways that I could not have known, my time with Dakota would give me a deeper understanding of my heritage and of the foundations of America.
Before my husband, Bruno, and I left Sarasota, I texted Dakota to make sure our Saturday lunch date in Hattiesburg was still good. She replied with a thumbs-up emoji.
Driving north on Interstate 75, Bruno suggested we leave the bland highway for a back road, Route 27. The first 30 miles were dotted with live oak trees tasseled with ghostly Spanish moss and the white split-rail fences of Florida horse country.
Then came towns whose names I learned from rust-streaked water towers. The towns offered a doleful refrain of billboards: Gun Shop, Bail Bond, Waffle House, Pawn Shop, Dollar General and Fried Chicken. I’d gone beyond my usual American contexts — New England, New York City, college towns.
After hours on Panhandle roads lined by malls, we were pleasantly surprised by Pensacola, a city of 56,000, which had a palpable sense of history and a handsome old-fashioned walkable downtown.
Though St. Augustine, Fla., founded in 1565, claims to be the oldest continuously inhabited European settlement in America, Pensacola predates it. A hurricane pulverized the first settlement, but in subsequent iterations, Pensacola was a place where different cultures lived together, and the architecture in its 40-block historic district recalls New Orleans, with meticulously restored Creole-style houses lit by gas lamps on streets with French and Spanish names.
The next day, I received a text from Dakota. Her grandmother had just gone into hospice care, and she was studying for final exams. “I have a lot going on right now,” she said. I wondered if she was going to cancel.
Bruno and I reached the flat shoreline of Mississippi, where the charm of arty Ocean Springs came from its Victorian wooden cottages with fretwork eaves, shade trees, jazz bars like the Julep Room and excellent restaurants. I found myself glancing at my phone so often I turned it off for a while.
Late that night my phone buzzed, and I jumped. Dakota texted me to choose the restaurant for lunch and let her know what time. I did some internet scrolling and chose a well-rated Thai place called Jutamas.
The Day Arrives
Rural Mississippi looked red and raw in the rain under a low pewter sky as we drove north to Hattiesburg the next day.
When we got to Jutamas, we sat at a table with elaborately folded black napkins and an orchid spray in a bud vase, and I nervously watched the vivid fish whose world had been reduced from an ocean to an aquarium.
Through the restaurant’s front window, I saw Dakota park, check her makeup in the rearview mirror and straighten out her gold hoop earrings before she came inside with a big soft smile. I saw her before she saw me, and I was awed by her poise and the bravery it took to come meet a middle-aged white man and his French husband, on her own. (I had suggested she bring her sister, mother or a friend, if it would make her more comfortable, but she said she’d come on her own.) I stood up and gave her a hug and a kiss on both cheeks. Then we sat down and just looked at each other and laughed. We shared an ancestor but were basically strangers.
Once a fumble of pleasantries had passed, and we’d ordered lunch, I delicately — I hoped — began to probe our family connection.
Dakota pulled out her phone and began scrolling through generations of photos of her family. She was descended from Philip Lobrano, one of Jacinto’s five sons. I’m descended from another of the sons, Dominick, and I didn’t know anything about the lineages of his other offspring.
As she scrolled, I was confused, because I could not tell whether the people in the older photos were Black or white. But, Dakota told me, her great-grandfather, Philip Posey Lobrano, had 11 children with a woman named Ana Floyd, who was one-eighth Black, making her what was classified as an “octoroon.”
In the next generation there was a photo of Dakota’s grandmother, Bertha Otkins Lobrano, an African-American woman. She had married Peter Lobrano, a son of Philip Posey Lobrano and Ana Floyd.
“Even though Peter Lobrano looked white, he had to take a Black bride because of his octoroon mother,” Dakota explained.
“In a small town like Centreville, Mississippi, everyone knew who had Black blood,” she went on. “The way the color line worked is that if you had any Black blood at all, you married someone else who was Black, because most white people didn’t mess with the color line.”
I began to apologize for my oversight, but Dakota waved it away. “I’m Black, and I live in the South, Alec,” she said. “It’s just baked into everything.”
She also told us that Philip Posey Lobrano had three sisters who lived in Centreville, but their descendants were not in touch with Dakota’s branch of the family. “They just swept us under the carpet,” she said. “We were an embarrassment to them.”
Dakota knew most of the same stories about Jacinto that I did, which made them ring true. She also mentioned that when she misbehaved as a child, her maternal grandmother would say, “That’s just your Lobrano acting up,” and shake her head.
By the time we took some selfies of ourselves in the parking lot, I was humbled. It was Dakota’s kindness and graciousness that had made our meeting so happy, for me anyway. Dakota said she hoped she’d see us again and I promised she would.
The squeaking of the windshield wipers in a thunderstorm woke me from a nap in the car while Bruno drove us back to our hotel. I sat in a silence swollen by the sweetness of having met Dakota. I also felt stung by my ignorance of her life as an African-American and the power of the color line in the American South.
Following in Jacinto’s footsteps
On a Sunday morning, as we neared New Orleans, a stiff wind was whipping up white caps on the broad briny waters of Lake Pontchartrain.
In the footsteps of Jacinto Lobrano, we wandered the candle-wax scented dimness of St. Louis Cathedral, where he’d married, and visited the Cabildo, which was built by the Spanish between 1795 and 1799 to house the government, to see the portrait of Jean Lafitte, the chief of Jacinto’s band of pirates.
We had dinner with my second cousin Ann and her husband, Gene, at Galatoire’s in the French Quarter that night. When I showed Ann and Gene a picture of Dakota on my phone, they nodded but didn’t engage.
Sitting in a flat-bottom boat during a bayou tour 16 miles south of New Orleans in the Mississippi Delta the next morning, I listened to the fascinating recitation of our guide-navigator with his beguilingly soft Cajun accent.
He pointed out sunning alligators and mentioned that these murky byways had once been the preserve of pirates. These were the steamy mosquito-ridden swamps where Jacinto had spent his youth. Until he’d given up piracy to run his sugar plantation and profit from human slavery, he’d been a thief, an outlaw and an outcast. It was astonishing to see how much storytelling, including his obituaries, and my family’s myth-making had tempered Jacinto’s ignominious biography into that of an eminent local grandee.
That afternoon, we visited the Confederate Memorial Hall Museum in New Orleans, where the silver sword Jacinto had received as a gift from Andrew Jackson is part of the collection, viewable by appointment. Wearing a pair of flimsy white muslin gloves, I held the heavy blade with a beautiful gold-chased silver scabbard. Of all the stories I’d heard about my great-great grandfather, the one I’d most doubted was the one about the sword. Suddenly, I desperately wished Dakota were there with me to share the moment.
We left New Orleans for the drive back to Florida, stopping at one point at a roadside picnic table. Unexpectedly, I welled up while unwrapping a turkey sandwich. My sudden gushing was fed by exhaustion, happiness, relief and shame, a very deep shame. I’d finally realized that the real reason for my trip was that I was seeking atonement. I’d failed, too, because there could be no atonement.
Still, if meeting Dakota couldn’t change the past, I still hoped we’d begun to repair an ugly rent in our family’s history with the only thing that might mend it: the truth.
When I later asked Dakota if she agreed, she hesitated. Then she said, “You’re family, Alec,” and I was very moved. “But I don’t know that we can ever really mend America, because racism was built into the foundations of this country.” I suggested we could try.
“I don’t know, Alec. I think it’s easier to be optimistic if you’re white than it is if you’re Black,” she said, adding, “But sure, at least maybe we can fix our own broken brick.”
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