
The life of Philip Benjamin (1779-1852) remains a mystery. But a review of his legal woes in the 1820s, when he was trying to raise a family, paints a clear portrait of him as a swindler. The first-generation Jewish American was in and out of court, losing case after case, with the exact ineffectual attorney, Abraham Moise, by his side.
Court records show that Benjamin had a habit of borrowing money from people, promising to pay it back, even in writing, and then not doing so. And these weren’t trifling amounts. He owed various creditors tens of thousands of dollars in today’s dollars. When courts consistently ruled against him, the Sheriff sold his home and then his business. His legal woes ultimately cost him his marriage.
As Benjamin was losing court battles, he had a family of seven young children at home, including my third great-grandmother Peninah, born in 1824, and her older sister Hannah, born two years prior. Benjamin’s oldest child, Rebecca, named after her mother, was a teenager. The family’s income depended on a dry goods store Philip ran at 165 Broad Street, according to an 1822 business directory.
It’s hard to imagine the legal turmoil must have brought to the family, especially Benjamin’s proud wife, Rebecca DeMendes Benjamin(1790-1847), who thought of herself as an impoverished aristocrat who had married beneath her standing.
The retailer’s legal woes started when William Caldwell sued him for an unpaid debt of $201. Benjamin had tried to pay Caldwell, a broker, with an endorsed $210 promissory note (a third-party check) signed by J. Joseph Jr. and dated December 26, 1826.
“It’s hard to say who J. Joseph was,” says my intrepid cousin, Karyn, a former government prosecutor who reviewed the court cases. Karyn is also an avid genealogist.” There was a doctor named Joseph Johnson and a mayor of Charleston (1825-1827) named Joseph during the relevant period. Neither seems likely to have signed a useless promissory note to Phillip Benjamin,” she says.
On April 26, 1827, Caldwell prevailed, and the court awarded him $388.43. According to numerous newspaper articles, William A. Caldwell sold just about anything — marble, estates, “negroes,” even an “elderly wench.”
The genesis for the next Benjamin case goes back to July 3, 1823, when the retailer borrowed $500 from John Dawson. The equivalent of $15,000 in today’s dollars, the loan was to be repaid with interest within the year. Dawson held Benjamin’s property as collateral. “This was essentially a short-term mortgage on the property,” says Karyn.
On July 7, 1824, Philip Benjamin paid Dawson one year’s interest on the loan, $35.00. He may have been able to afford more. Only three months before, on April 23, 1824, he sold four enslaved people (Nancy, Mary, Betty, and Archy) to A.S. Wellington for $1,020.00. Benjamin enslaved people nearly to his death. Thirty years later, the 1850 census still shows him enslaving people.
By October 15, 1825, three months later, Benjamin still hadn’t paid any more interest on the loan. The court summoned him to appear on January 1, 1826, and answer the complaint, a breach of contract for $500. The court, which couldn’t locate Benjamin, left the summons at his home and ordered a jury trial in the Court of Common Pleas. On January 25, 1827, the jury found that Philip Benjamin owed John Dawson $500 plus $36.59 in damages.
“This may have been a trial in absentia since the Sheriff could not locate Benjamin and just left a notice at his residence,” says Karyn. Notes in the docket indicate the sole issue for the jury was the authentication of Benjamin’s handwriting on the promissory note.”
The verdict cost Benjamin his home and property.

“The Sheriff’s office ran a sales notice in The Charleston Daily Courier on April 30, 1827. “All that two story House, and Lot of Land, situate, lying and being on the west side of King St. adjoining the residence and store of Bartholomew Clark. Levied on and to be sold as the property of Philip Benjamin, at the suit John Dawson. Conditions cash.”
The sale must have been successful because, on July 10, 1827, the Dawson case’s judgment (debt and damages) was deemed satisfactory.
“That same year, on January 3, 1827, the court issued a summons for Philip Benjamin to appear and answer complaints by Mackie, Hervey & Company, which seemed to broker passage and goods on shipping lines. Again, the hapless Abraham Moise, like Benjamin, a member of Charleston’s Reformed Society of Israelites, represented the plaintiff.
The complaint alleged a breach of contract “for certain promises and assumptions made and not performed.” That same year, on January 3, 1827, the court issued a summons for Philip Benjamin to appear and answer complaints by Mackie, Hervey & Company, which seemed to broker passage and goods on shipping lines. Representing the plaintiff once again was the hapless Abraham Moise, like Benjamin, a member of Charleston’s Reformed Society of Israelites. The complaint alleged a breach of contract “for certain promises and assumptions made and not performed.”
The company alleged $580 in damages. That means that in 1827, Benjamin, a father of seven, had at least $1080 in unpaid debt, the equivalent of about $32,000 in today’s dollars.
“Benjamin first offered to pay Mackie, Hervey & Company about half the amount in question, a tactic he tried several times, never with success. ” ”Judgement by Confession” settlement entered on April 11, 1827, awarded the complainant $289.92 plus $30 for costs. Benjamin made the offer the same month the Sheriff offered his home for sale.”Benjamin first offered to pay Mackie, Hervey & Company about half the amount in question, a tactic he tried several times, never with success. A ”Judgement by Confession” settlement entered on April 11, 1827, awarded the complainant $289.92 plus $30 for costs. Benjamin made the offer the same month the Sheriff offered his home for sale.
The ploy didn’t sit well with the complainant, who issued a demand for nonpayment (Declaration on Note) and a suit for the original demand of $580.00. The document alleged that Philip Benjamin had given many false written promises to pay the settlement amount. The Mackie case cost him his business.
On May 14, 1827, a Sheriff’s sales notice ran in the Charleston Daily Courier. “Sundry articles of Groceries, etc. being the remains of a Grocery Store, situated at the corner of King and Ann streets. Levied by and to be sold as the property of Philip Benjamin, at the separate suits of Mackie, Hervey & Co and Adger & Black (see that lawsuit below). Conditions cash.”
Then his bankers, Adger & Black, came after him in May of 1827, again represented by the ineffectual Abraham Moise, who remarkably became a magistrate judge. A court issued a summons for Benjamin to answer complaints in court. The complaints alleged a breach of contract “for certain promises and assumptions made and not performed.”
The sharks were indeed circling. The company asked for a whopping $1,095.00 in damages, double what Benjamin already owed to others.
Once again, Benjamin attempted to settle for half. In a “Judgment by Confession” entered on April 11, 1827, he offered $547.55 plus $30 for costs. But the bank, likely encouraged by previous judgments against the dry goods dealer, wanted full repayment of $1,095.00. In a new allegation, the bank noted Philip Benjamin’s written promise, dated March 26, 1827, to pay the settlement amount.
The bank’s insistence on full repayment came a week and a half after the Sherriff’s May 14, 1827, notice to sell the “remains” of Benjamin’s grocery store.
The following month, to protect herself from her husband’s creditors, the proud Rebecca Benjamin announced that she was going into business for herself, or at least taking over what remained of her husband’s business. The Charleston Daily Courier ran a June 7, 1827, notice: “Rebecca Benjamin, wife of Philip Benjamin, Grocer, hereby notifies her intention of becoming a Sole Trader in one month from this date.” The notice ran several times after that.
The following month, to protect herself from her husband’s creditors, the proud Rebecca Benjamin announced that she was going into business for herself, or at least taking over what remained of her husband’s business. The Charleston Daily Courier ran a June 7, 1827, notice: “Rebecca Benjamin, wife of Philip Benjamin, Grocer, hereby notifies her intention of becoming a Sole Trader in one month from this date.” The notice ran several times after that.
This wasn’t an unusual ploy. Several Charleston businesses were run by women whose husbands had given them ‘sole trader’ status. Under coverture laws, married women were the legal property of their husbands, although their husbands could grant them independent economic status through a legal document.
The historian James Hagy identified 48 Jewish women as “sole traders” between 1766 and 1827. Many helped run their husbands’ businesses when the men were away. In other cases, women would take over the family business when it was not doing well.
Wrote Hagy, “Rebecca De Mendes Benjamin, the mother of future Confederate leader Judah P. Benjamin, was given sole trader status by her husband when his dry goods store was in dire financial straits. Rebecca took over the business. Later, she owned a store in Beaufort while her husband remained in Charleston.”
Some creditors with more minor claims also came after Benjamin in 1827. On January 1, 1827, Joseph Marks, a liquor dealer in town, claimed that Benjamin owed him $134.83. On February 16, 1828, a jury ruled in favor of Marks, awarding him $181.49, including costs and interest from February 1827.
Rebecca’s attempt to establish an independent business didn’t insulate her from lawsuits. She was summoned to appear in court on January 1, 1838, after John Lloyd alleged she reneged on a nine-month promissory note. Benjamin allegedly signed over the $433.81 note from the Union Bank in Charleston to Lloyd in September. Lloyd said he was not satisfied when attempting to redeem the note. He alleged $807 in damages.
Abraham Moise, defending Rebecca, claimed that she did not promise in the manner described. Rebecca ultimately signed a promissory note to John Lloyd for $333.81 after a jury assessed damages for that amount. The jury further found her liable for costs of $23.50. Satisfaction of the judgment against Rebecca Benjamin was entered on February 2, 1839.