Middletown African American Revolutionary War vet honored for service after 175 years

MIDDLETOWN — Jesse Sip Caples of Middletown, an African American Revolutionary War veteran among the indigenous inhabitants of the city, risked his life and was imprisoned for a time to help the colonies gain freedom from the British Empire.   

Caples, a member of the Wangunk Tribe who lived to more than 100, was born in Middletown in 1743, married three times, and survived two of his wives. He left the world with 10 children. 

No one is really sure whether Caples was a free man or enslaved, according to Middlesex County Historical Society Executive Director Jesse Nasta.

Earlier this month, Caples’ descendants gathered with representatives from the Greater Middletown Military Museum and others for a ceremony to mark the grave of the man who died in Middletown in 1847. Caples was buried in the Washington Street cemetery across from the Beman Triangle, a neighborhood established the same year by a Black man for other Black homes.

The ceremony took place on Veterans Day. Museum President Kenneth A. McClellan, who served 30 years in the U.S. Army, National Guard and Reserves, said the federal government paid for the grave marker at the site.

The ceremony drew approximately 20 observers, including about 10 descendents, said Frank Reese of Bridgeport, who added that Caples is his fourth great-grandfather. Several of those attending were cousins of Reese who live in Connecticut. 

“I was so grateful and so thankful,” Reese said of the effort to erect a grave marker. “It was awesome, and I feel a stronger connection to my ancestors.”

The stone marking Caples’ grave was placed next to his grandson, who fought in the Civil War. Reese also said Caples helped build the ship he was on — the Confederacy — when it was captured by the British.

Caples served in the Confederacy in 1779, which set sail to France to transport an American diplomat and was later captured by the British in 1781, museum records show. He was held by the British with other Confederacy soldiers on the British ship HMS Jersey. He was ultimately paroled in 1782.

In his pension application, Caples wrote: “On our passage home, we were captured by a British squadron in April 1781. I was then carried to New York and put on board the Jersey prison ship, where I remained until I was regularly exchanged in the month of July following, the whole time of my service embracing a period of more than two years.”

While Caples fought to secure his country’s independence, it is unclear if Caples was a free man.

Nasta, a professor of African American Studies at Wesleyan University, said whether Caples was free or enslaved remains a mystery considering Caples was a member of a Native American tribe.

“We don’t really know if he was considered a free Native American or classified as an enslaved person of African American descent,” said Nasta, who grew up in Middletown and still lives in the city. While Native Americans were enslaved in New England in the 1600s, by the 1700s “they weren’t supposed to be enslaved,” he pointed out.

At the time of the Revolutionary War, there were about 5,000 people enslaved in Connecticut, its peak, said Nasta, who added that, afterward, slavery began to decline throughout New England.

More than 200 African American men from Connecticut fought in the war for the Continental Army, Nasta explained. Some of those men were free, and others were freed as a result of fighting as proxies for their owners.

Connecticut law at the time allowed for freeing African American slaves who fought in this way, but did not require it, the executive director noted.

There are many “unknowables about his personal history,” Nasta said.

He estimated that Caples has more than 1,000 descendants, including Thirman Milner, mayor of Hartford from 1981 to 1987, and the first African American municipal leader elected in New England. 

Despite some holes in Caples’ biography, Nasta said, “we need to get this information (about the contribution of African Americans at the earliest points in American history) into the public’s consciousness.”

The general perception may be that New England was a “historically white region,” but, in fact, “African American and Native Americans were also shaping Connecticut and New England history … Enslaved people were essential to New England society,” Nasta explained. 

Nasta said Caples’ story being rooted in Middletown brings issues surrounding justice and fairness into concrete form. “It’s not an abstract debate,” he said. “This brings it home. It’s about people who are buried right here and whose ancestors are here in Connecticut. There were hundreds of others who fought in the American Revolution.”

Reese agreed the public needs to know about the contributions of Caples and other African Americans during the nation’s founding.

“It is a shame it took 175 years for him to be acknowledged for his years of service in the Revolutionary War,” Reese said. “Not a lot of people knew about him.”

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