If Freeman looked the other way, in 1883, she might notice the building boom going on all around her two-story clapboard and brick house. Over night, new homes seemed to be going up. Carpenters were everywhere. There was a steady rhythm of hammer-slamming, the clatter of lumber. Morning, noon and late into the afternoon. Six days a week. Every day but the Sabbath.
Businesses like Warner Co., makers of the patented elastic girdle, and Bridgeport Brass were putting up houses. They had to to attract workers. Prices were dropping because of a glut in supply. And even though workers might find themselves out of a job at one factory, there often was another one waiting to hire them. The situation was as close to full employment as it gets. Anyone who wanted a job could find one. People were pouring into Bridgeport, which some sources, like Scientific American, proclaimed as an industrial powerhouse. A place where any entrepreneur worth anything wanted to set up shop. By the 1880s, Connecticut had more foreign-born workers than almost any other state with the exception of Massachusetts.
Freeman was in her early 40s when she followed her elder brother, Joel Freeman, from Derby to Bridgeport to buy property. She had sold
"Even though a lot of what these black governors did was largely ceremonial, they had power," Derby Historian Robert Novak says. "A lot of that influence no doubt got passed down to Roswell's daughter, Mary Freeman, who amassed a fortune for herself."
Freeman's brother Joel persuaded the Connecticut General Assembly to pay for a library in their African-American community, Little Liberia, at a time when the rest of Bridgeport didn't have a single library. In fact, the African-American community in the Park City had a library for at least 37 years before the rest of the city.
After her mother's death, Freeman headed to Bridgeport in the early 1840s and began buying land and buildings. At the time she was working in New York City for one of the leading hotels, where the clientele liked Southern-style cuisine.
"The Howard House hotel in New York was one of the fanciest hotels that employed black waiters and chefs, although they tended to be European," says Daniel Levinson-Wilk, a professor who teachers New York City history at the Fashion Institute of Technology. Levinson-Wilks researches and writes about the African-American influence in the 19th century hotel industry. "Tunis Campbell was the head waiter at the Howard House, and he was a fairly well-known abolitionist minister who financed some of his abolition activities through his hotel employment," Levinson-Wilks says, adding that from the Howard House, Campbell wrote "the first hotel management textbook" and after the Civil War enjoyed a career in politics in Georgia during Reconstruction.
Did Freeman and Campbell know each other? Levinson-Wilks is unsure. He thinks it's possible and he intends to use census records from the 1830s and 1840s to investigate.
Back in Connecticut, William D. Bishop was putting together narrow tracks of land that eventually would become the New Haven Railroad. Freeman was in the right place at the right time. She flipped some of her properties, speculated on land in Bridgeport and constructed several rooming houses. Bridgeport Historian Charles Brilovitch and the National Register of Historic Places believe Freeman's rooming houses were a northern stop on the Underground Railroad and that she was responsible for helping runaway Southern slaves reach freedom.
One of Freeman's tenants was an elderly emancipated slave in her 80s. One night the woman was severely burned in a fire when a lit candle fell and ignited her blanket. Firefighters asked Freeman for permission to bring the woman into Freeman's home across the street. She refused. A few hours later, the elderly fire victim died of her burn injuries.
The circumstances surrounding the tenant's death touched off a police investigation, but Freeman was never charged with any crime. Neighbors speculated that Freeman may have had a reason for wanting to keep them out of her house. Some of them believed that unsavory activity was taking place in her home.
Perhaps gossip in the community dogged Freeman or maybe she just wanted a change. But she left the Baptist church where she belonged for years for another house of worship farther from her home.
Freeman was well known in Bridgeport's South End African-American community, known as Little Liberia, although Brilovitch says he now believes Freeman also was part Native American, a Golden Hill Paugussett.
She was educated. She was well spoken and most important in her community, she could sign her name. She could sign and witness legal documents for those who couldn't. She could loan money and hold mortgages for fellow African-Americans so they could have houses of their own when the established banks wouldn't give them the time of day. All of this made her popular and influential.
When she died on March 13, 1883, a day after revoking a long-standing will, she was estimated, Brilovitch says, to be worth about $100,000 in 1883. That's equivalent to $2.3 million in 2008 dollars, according to Todd Martin, an economist with People's United Bank in Fairfield. Even by today's standards an estate worth that figure is sizeable.
The secret of her success
How did Freeman amass that fortune? Was it just land speculation and renting out rooms? Bridgeport Reference Librarian Mary Witkowski and Novak of the Derby Historical Society wonder if Freeman also ran a bordello. Her tenants were all women. Most of them were young, Witkowski says. And all of them were single like Freeman and her sister Eliza.
"The day Mary Freeman's house was put on the National Historic Register, I stood outside her place for the dedication," Witkowski says. "Obviously, she was a shrewd business person. But I looked outside the house and I thought about how she never married, the tenants she had and I wondered if she had been a madam and run a prostitution house."
Freeman's original will had left almost of her real estate and personal property to her former Methodist minister, the Rev. Albert Nash, who had moved to a new church in Norwalk.
Her new will, drafted and witnessed a day before her death, left the bulk of her estate to the physician who treated her in her final illness, Dr. A.A. Holmes. Among Freeman's last wishes was to be buried near her mother in Derby and for Holmes to have Freeman's name inscribed on the headstone that she put up over her mother's grave.
Freeman's second will is brief, running for only a couple of paragraphs.
"Holmes may have had her buried there," Novak says. "But he never had her name put on the tombstone. It's not there."
Besides signing off on Freeman's death certificate, listing her cause of death at 65 as the result of a respiratory illness, Holmes put his name to 16 other death certificates in that same period.
He sold Freeman's Sea Cliff cottage and successfully fended off a double attack on Freeman's will, one of which came from Freeman's brother in Massachusetts, the other from Freeman's former pastor.







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