David Wooster is known more as the person who gave New Haven’s Wooster Square neighborhood its name than for his heroism during the American Revolution. He’s even less known as an abolitionist.
Centuries after his death, the revolutionary war general got caught up in the Battle of Wooster Square, a conflict over symbols of ethnic and racial pride.
On June 24, 2020, a crew hired by the city took down the statue of Christopher Columbus in Wooster Square, New Haven’s Little Italy. Italian-Americans protested the removal of the statue that symbolized their heritage. As the statue came down, they clashed with black, Native American and Latino protesters who said Columbus represented the evils of colonial conquest.
Two days later, a group of people met with state Rep. Roland Lemar to ask to rename Wooster Square after William Lamson, a black New Haven entrepreneur in the early 19th century. That did not sit well with the Italian-American community, which submitted a petition with 3,000 names asking to keep the name “Wooster Square.”
Perhaps a closer look at the life of David Wooster would change some minds (or not).
He was born into a well-to-do family in Stratford, Conn., on March 2, 1711, the youngest of six. His Puritan parents, Abraham and Mary, imposed a severe and sober discipline.
Wooster graduated from Yale College and then earned his master’s degree. In his early 30s he commanded the first warship built in Connecticut, the Defense, to defend the East Coast from pirates and smugglers. During his time on the Defense, “the shores of Connecticut were unpolluted by pirate invasion,” according to the oratory on the dedication of his monument.
In 1745, David Wooster married Mary Clapp, the daughter of Yale President Thomas Clapp. They had four children and bought a gracious house in New Haven. The house survived British arson but not urban renewal. The Woosters entertained frequently, employed black servants and kept a phaeton for rides around town.
In 1758 David Wooster led Connecticut forces at the Siege of Louisburg. His gallantry earned him the right to bring a ship of prizes and prisoners to France and England. The English feted him, and he was “gladdened with the sunshine of the royal smile.”
He also served six years in the French and Indian War, rising to the rank of colonel. Afterward, New York granted him 3,000 acres of Vermont, but he lost it to squatters. Nevertheless, he prospered. Both he and his wife inherited money, and he earned quick and substantial profit as a merchant.
Yale President Theodore Dwight called him a “brave, generous-minded man, respectable for his understanding and for his conduct both in public and private life, ardent in his friendships and his patriotism, diffusive in his charities and steadfast in his principles.”
In 1773, Wooster received a letter from Phillis Wheatley, the first published African-American poet. She had astonished Bostonians with her work. They couldn’t believe a young black slave could write such poetry. Wheatley proved them wrong, and moved to England. There she became the darling of abolitionist circles and tried to publish her first book. So she asked Wooster for help.
She apparently didn’t know him, but knew of him through a servant of his neighbor, a Mr. Badcock. She must also have assumed he would sympathize with her.
Wheatley in her letter asked Wooster if he would help sell her first book of poems. John Wheatley, she wrote, had just given her her freedom, and she knew she’d have to make her own way in the world. She asked Wooster if he would use his influence with the gentlemen and ladies he knew to subscribe to her poetry. (Back then, people subscribed to books before their publication.)
“The more subscribers there are, the more it will be for my advantage as I am to have half the Sale of the Books,” Wheatley wrote. “This I am the more solicitous for, as I am now upon my own footing and whatever I get by this is entirely mine, & it is the Chief I have to depend upon.”
For God, for Country and for Yale
Wooster believed ardently in independence from Britain–and for enslaved people. In the war’s early days, Benedict Arnold and Ethan Allen got credit for seizing Fort Ticonderoga, but David Wooster helped plan the attack and lent money for it.
In May 1775, the Connecticut General Assembly appointed the 64-year-old businessman a major general of a militia regiment. Before marching off to war, he assembled his regiment on the New Haven Green and led them in prayer. His pastor, Jonathan Edwards, also an abolitionist, couldn’t make it.
Wooster then led patriot forces in the ill-fated expedition to Quebec and returned home. He received a new command of the Connecticut militia, and he paid his men and officers with his own money. Still, he hoped his country would repay him. So he asked for receipts. But British soldiers burned his house after his death with the receipts inside. His wife ended up in debtors’ prison.
Battle of Ridgefield
Charged with the defense of Connecticut, he got word that on April 25, 1777, British Gov. William Tryon had invaded Connecticut at Westport with 2,000 troops. Tryon’s forces marched 20 miles north toward Danbury to destroy military supplies.
Along what is now Rte. 28, the British ravaged the land. They then burned Danbury.
Wooster and Benedict Arnold, who happened to be staying in New Haven, responded to the British with 700 militiamen and Continental Army soldiers. The British retreated toward Ridgefield, burning houses along the way.
On April 27, Benedict Arnold barricaded the center of Ridgefield. He received reinforcements, but the British drove them off in a running battle down Main Street. Wooster tried to rally his undisciplined militia with the words, “Come on, my boys, never mind such random shots.” A ball then hit him in the back, severing his spine. A small Masonic stone memorial marks the place where he fell from his horse at the intersection of the Post Road (Route 1) and Patriots Bank.
His men carried him from the field to a nearby house. The surgeon told him he had no hope. Wooster suffered agonizing pain for the next five days. His wife Mary came to his deathbed, but he didn’t recognize her until the end. He died on May 2, 1777.
After Wooster’s death, poet Phillis Wheatley wrote a letter of condolence to his widow – one lost to history until rediscovered around 1980. In it, she thanked Mary for selling her poems to their friends. She also praised David Wooster while pointing out the hypocrisy of those who supported independence from Great Britain but not for the enslaved.
“I sincerely sympathize with you in the great loss you and your family sustain,’ Wheatley wrote.
“You will do me a great favor by returning to me by the first oppy those books that remain unsold and remitting the money for those that are sold–I can easily dispose of them here for 12/ Lmo. (12 shillings lawful money) each–I am greatly obliged to you for the care you show me, and your condescention in taking so much pains for my interest–I am extremely sorry not to have been honour’d with a personal acquaintance with you.”
Wheatley also enclosed a poem, one not terribly admired by critics, that lauds Wooster as a martyr for freedom:
He nobly perish’d in his Country’s cause
His Country’s Cause that ever fir’d his mind
Where martial flames, and Christian virtues join’d.
Long after their deaths, developers built a desirable residential neighborhood around a square named after Wooster. Sea captains and prosperous businessmen bought homes in Wooster Square. Then, following a typical urban trajectory, the neighborhood declined as industry moved in. Then in the late 19th century, Italian immigrants crowded into the old buildings and ran shops and restaurants.
The city slated Wooster Square for urban renewal in the 1930s, but plans changed by the late 1950s. Postwar prosperity allowed preservation and gentrification to make the neighborhood, once again, a desirable place to live.
And then in 2020, another battle – over a statue and a name.
With thanks to Slavery, Abolition and Emancipation Vol 1, edited by David Dabydeen, Sukhdev Sandhu.
Images: Center Church on the Green, By Dicklyon – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=79216980. Frank Pepe’s By Krista – frank pepe exterior, CC BY 2.0, https://commons.wikimedia.org/w/index.php?curid=38640336. This story was updated in 2022.