Episode 4.2 A Young Lady in Philadelphia

[Transcript]

Hello, and welcome to America’s First Ladies. I’m your host, Risa Weaver-Enion.

Episode 4.2 A Young Lady in Philadelphia

We left off last week in the mid-1780s. Dolley and her family had moved to Philadelphia in 1783, the war officially ended late in 1783, and they were living in their own house by 1785. Teenage Dolley was making her presence known in the City of Brotherly Love.

Richard Côté quotes an unnamed writer in his book Strength and Honor: The Life of Dolley Madison when he writes that Dolley was “exceptionally pretty by the standards of her time, with a natural vivacity. Even at fifteen she had a magnetic quality that drew people to her, an attraction that a later age would call charisma. People were always aware of her proximity. Men stared at her when she walked down the streets and at social gatherings she became the center of attention.”

I don’t know the gender of the original source for that quote, but they certainly seem to be unaware that having men stare at you while you walk down the street is not something to hope for in life.

Dolley was also described around this time as being “of slight figure, possessing a delicately oval face, a nose tilted like a flower, jet black hair, and blue eyes of wondrous sweetness.” 

One of Dolley’s favorite pasttimes after moving to Philadelphia was people-watching along the river on fashionable Chestnut Avenue. Although she couldn’t partake of fine fashions, she enjoyed looking at the upper classes in their finery. One contemporary observer chronicled the fashions of the day:

“The men were arrayed in very tight small-clothes and silk stockings with pointed shoes ornamented with shining buckles. Their waistcoats were often bright colors, and the outer coats with several little capes were adorned with silver buttons, from whose size and number the owner’s wealth might be guessed. … The women were attired even more gorgeously than the cavaliers…Their gowns of brocade were of a prodigious fullness as needs must be when the hoop spreads out like a balloon. The musk-melon and calash bonnets were of correspondingly wide dimensions, and altogether a woman prepared for the promenade resembled a ship under full sail.”

As a Quaker though, Dolley was forced to wear infinitely less interesting clothes. As Richard Côté describes, “Mary Payne saw to it that Dolley was clothed in a long, plain, shoe-length, gray dress, devoid of buttons, tucks, or gathers; a simple, high-necked, white blouse; a shawl (if weather required); and a large, close-fitting, white sunbonnet into which her black curls were tucked. The ensemble was completed with gloves to cover her arms and hands and a white linen facemask to protect her fair skin from the sun, and her face from undue attention by male strangers.” 

When we get to Dolley’s later years, when she is a fashionista of the highest order, remember this description. I think it goes a long way toward explaining her later tendencies.

Dolley’s social life expanded dramatically after the move to Philadelphia. There were two locales just outside the city where Dolley and her friends would take excursions: Haddonfield, across the Delaware River in New Jersey and Gray’s Ferry, along the Schuylkill River.

In Haddonfield, the young people would gather at Creighton Tavern, which is now the Indian King Tavern Museum. There was a large assembly room upstairs where music and dancing would take place. Dolley couldn’t participate in the dancing, but she apparently enjoyed the excitement of these events. Gray’s Ferry was lined with shops where Dolley and her friends could admire, but not purchase, all the finery and fashions that they weren’t allowed to wear.

During the summer of 1787, when Dolley was 19, Philadelphia was host to the Grand Convention, which we now call the Constitutional Convention, because the U.S. Constitution was drafted there, even though that wasn’t the original intention of the convention. We’ll talk much more about this in episode 4.4 because James Madison was a key player at the convention. So he and his future wife were definitely in Philadelphia at the same time, but they did not cross paths.

In 1790, the capital of the United States moved from New York City to Philadelphia, as part of the deal we discussed in episode 1.9, whereby Alexander Hamilton’s financial plan for the country was adopted, the capital was moved to Philadelphia for 10 years, and then the site for a new capital city along the Potomac River would be chosen by George Washington.

James Madison was a member of the House of Representatives when the capital moved to Philadelphia in 1790, but again, he and Dolley did not meet. And by then, Dolley was already married to her first husband, John Todd. So let’s get to know John a little.

John Todd, Jr. and Dolley Payne first met in 1786, when her family joined the Pine Street Meeting in Philadelphia. John was a Quaker son of Quaker parents. At the time of their meeting, John would have been 23 or 24 and Dolley would have been 17 or 18, depending on the time of year they met. John worked as a lawyer, his brother James was a bank clerk, and their father was a schoolmaster. No plantation owners in this family!

Dolley most likely had several suitors, but she seems to have genuinely preferred John Todd. Their romance was the subject of conversation among Dolley’s friends. Before I read you the next quote, I want to point out that this quote is one long run-on sentence. You may recall in episode 4.1 I described Dolley’s writing style as less than polished. This was apparently common among her friends as well.

One young lady wrote to another, “Dolly [sic] Payne is likely to unite herself to a young man named J. Todd, who has been so solicitous to gain her favor many years, but disappointment for some time seem’d to assault his most sanguine expectations, however things have terminated agreeable to his desires & she now offers her hand to a person whose heart she had long been near and dear to—he has proved a constant Lover indeed & deserves the highest commendation for his generous behavior as he plainly shows to the world no mercenary motives bias’d his judgment (on the contrary) a sincere attachment to her person was his first consideration else her Father’s misfortunes might have been an excuse for his leaving her.”

The misfortunes referenced in the letter relate to the failure of John Payne’s laundry starch business. In 1789 he went bankrupt, which was not only a financial problem for the family, but a religious one as well. Quakers considered financial solvency to be part of godliness, so John Payne was expelled by the Pine Street Meeting. The rest of the Payne family remained members of Pine Street, but John Payne joined a new meeting, the Free Quakers, a less dogmatic group. They had actually supported the patriots in the Revolutionary War, and some members had even taken up arms on behalf of their country.

Despite being welcomed into a new Society, John Payne’s financial difficulties drove him into a deep depression. He spent most of the rest of his life in his bedroom, turned to face the wall, not engaging with anyone.

In the midst of all this, Dolley and John Todd became engaged. Like everything else in the Quaker religion, permission to marry required an investigation. First, the couple had to formally announce their intention to marry at one of the monthly meetings. The groom-to-be would enter the women’s side of the meetinghouse with a friend from the men’s division, then he would take his intended bride by the arm and announce, “We propose taking each other in marriage.”

Then the bride and groom would be investigated, and if no objections to their marriage were raised, they were given permission to marry at the next monthly meeting. This was known as “passing meeting.” Dolley and John Todd were approved, and they were married at the monthly meeting on January 7, 1790. Dolly was 21 and John had just turned 26 the prior November.

There are no surviving eyewitness accounts of Dolley and John’s wedding, but based on Quaker traditions at the time, we can surmise how it unfolded. Because the marriage took place at the monthly meeting, the meetinghouse would have been full of regular members and possibly non-Quaker friends of the couple. John and Dolley would have faced each other, holding hands. John would have first declared that he took Dolley as his wife, promising “with Divine assistance to be unto thee a loving and faithful husband until death should separate us.” And then Dolley would have made the same declaration.  

Then they would have signed the marriage certificate, followed by Dolley’s bridesmaid, Eliza Collins; John’s groomsman, Anthony Morris; and 82 other witnesses. One can only assume the marriage certificate was very large. And then presumably, the monthly meeting unfolded in its usual way.

Richard Côté quotes an earlier biographer of Dolley in writing about Quaker wedding entertainment in late 18th century Philadelphia:

“Marriage entertainments at this time were very extensive, and harassing to the wedded. For two days afterward punch was dealt out in profusion, and, with cakes and other sweetmeats, were set out on the lower floor, and were also sent out generally throughout the neighborhood, the bride received the visitors, and was kissed by all comers, often as many as a hundred a day. The richer families also had as many as one hundred and twenty to dine and stay to supper the day of the marriage. All who signed the marriage certificate were also invited to tea or supper.”

Given the Payne family’s financial straits, it’s probably safe to assume that they scaled back these entertainments dramatically. They certainly couldn’t afford to provide supper, or even tea and cake, for close to 100 people.

We don’t know what Dolley wore for her first wedding, but another Quaker bride at the time lamented her plain wedding dress, writing, “My wedding gown was ashen silk, too simple for my taste; I wanted lace around the neck, and a ribbon at the waist.” It’s a good bet that Dolley also found her wedding gown to be lacking in the ornamentation department.

It’s likely that the new Mr. and Mrs. Todd lived with Dolley’s parents at first after the wedding. At some unknown point before 1791, Mary Todd turned the home into a boardinghouse to bring in some money. When the capital moved to Philadelphia in the summer of 1790, many federal officials were looking for rooms or homes to rent, so it was a good time to get into the boardinghouse game.

On January 23, 1791, John Todd puchased a home for himself and his wife at the corner of Fourth and Walnut streets. It was a three-story red and black brick dwelling with an adjacent two-story brick kitchen and a wooden stable. The house had an excessive number of windows, which were quite expensive at the time. The front of the house had two doors, eighteen windows, and two attic dormer windows. It was a stately, substantially sized home. John used a room in front on the first floor as his law office, and a second room was used by his law clerks and apprentice.

An inventory of the home’s contents in 1793 shows a great deal of tasteful, high-quality furniture, including a large sideboard, a settee, 11 mahogany and pine tables, 36 mahogany and Windsor chairs, 3 mirrors, china, carpets, 6 pieces of artwork, and various other goods. The family library was equally impressive, boasting around 150 books valued at £187, which is roughly $45,000 in 2026 money. That’s a lot of books.

Dolley and John soon began to add children to their home. The first child, a son named John Payne Todd, was born on February 29, 1792. Thankfully, this child was called Payne, so we don’t have two John Todds running around in this podcast. 

Later that year, on October 24, 1792, Dolley’s father died. He had known the end was coming, having made out a will on September 2. His wife Mary was the executor, and John and Dolley Todd were witnesses. John Payne’s funeral service was held at the Free Quaker meetinghouse, and he was buried in the Free Quaker cemetary on Fifth Street.

The following year, 1793, brought more heartache to Mary Payne. Dolley’s younger sister Lucy eloped at the age of 15 with a non-Quaker, who just so happened to be George Steptoe Washington, 17-year-old nephew of President George Washington. And we know what happens to Quakers who marry non-Quakers, right? They are disowned by their meeting, which is what promptly happened to Lucy, bringing further shame to Mary Payne.

As the minutes of the monthly meeting describe, “Friends are appointed to assist women Friends in preparing a testimony against the misconduct of Lucy Washington, late Payne, who had by birth a right of membership among us, having disregarded the wholesome order of our discipline, in the accomplishment of her marriage with a person not in membership with us, before a hireling priest, and without the consent of her mother, after being precautioned against such outgoing. We therefore testify that the said Lucy Washington is no longer a member of our religious Society, nevertheless desiring she may be favored with a due sense of her deviation and seek to be rightly restored.”

Lucy did not, in fact, view her marriage as a deviation, and would never seek to be restored to the Society of Friends. After having both her father and her sister disowned by the Quakers, Dolley’s ties to the Friends were beginning to fray.

But Dolley and John were enjoying their growing family and their prosperous life. On July 30, 1793, while out riding circuit to various courthouses, John sent Dolley a warm, loving letter, writing, “I hope my dear Dolley is well and my sweet little Payne can lisp Mama in a stronger Voice than when his Papa left him—I wish he was here to run after Mrs. Withy’s Ducks, he would have fine sport—Let the Boys be attentive to the office and Business. I have no doubt of my Dear Dolleys Assistance when necessary. Thine forever, John Todd Junr.”

I find it amusing that he signed his full name to this letter.

But there’s nothing amusing about what happened next. Note the date of that letter: July 1793. You should know by now what’s coming. That’s right, the great yellow fever epidemic of 1793. We’ve discussed this in both season 1 and season 2, but we’re going to get into it again because it had a profound impact on Dolley’s life. In fact, without the yellow fever epidemic, we very well might not be here today, listening to Dolley’s life story.

On August 5, Dr. Benjamin Rush recorded his first case of what he called “the malignant fever.” Yellow, jaundiced skin was one symptom of it, which is why it was called yellow fever. Yellow fever outbreaks were common, but no one yet understood how the disease was transmitted. They didn’t know that infected mosquitoes transmitted it, or that the standing water that attracted mosquitoes was a problem. We already heard about how dirty parts of Philadelphia were at this time. And as a port city, standing water was everywhere.

By mid-September, dozens of people were dying each day. Thomas Jefferson was in Philadelphia at the time, and on September 8 he wrote to James Madison, “The yellow fever increases. The week before last 3 a day died. This last week about 11 a day have died, consequently, from known data about 33 a day are taken and there are about 330 patients under it.”

One doctor graphically described the suffering of one of his patients, “severe head and back pains, great thirst, offensive stools, much vomiting, delirium, red spots on the face and breast, blindness, sore throat, hiccupping, and death.”

In the midst of this chaos, Dolley gave birth to her second, and, ultimately final, child in September. It was another boy, and they named him William Temple Todd, after Dolley’s older brother. (I’ll note here that Wikipedia claims that William Temple Todd was born on July 4, but there’s no citation, so I’m sticking with the September reference included in Richard Côté’s book.)

Dolley and William were both fragile and weak after the birth, so John moved them to Gray’s Ferry. Young Payne Todd went with them, as did Mary Payne and most likely her younger children, Anna, Mary, and John.

John Todd returned to the city to take care of his parents and to tend to legal work. His faithful clerk, Isaac Heston, also stayed behind. Their practice was swamped with the grim business of drawing up wills for the dying residents of Philadelphia. Isaac wrote to his brother, 

“You can not imagine the situation of this city. How deplorable. It continues to be more and more depopulated, both by the removal of its inhabitants into the Country, and by the destructive Fever which now prevails. They are Dieing on our right hand and on our left… in fact, all around us, great are the numbers that are called to the grave, and numbered with the silent Dead. Through all the danger, thanks be to God, we have yet been preserved, but how long It may continue so, it is impossible to say, for this hour we may be well, and next find ourselves past recovery.”

Their preservation would not continue for long. On September 29, Isaac Heston died of the fever. On October 2, John Todd’s father died, followed by his mother on October 12. Then John came down with the fever himself. Yellow fever is not transmitted from one human to another, only by mosquitoes. But by remaining in Philadelphia as long as he did, John left himself open to the higher risk of infection in the city.

Meanwhile, Dolley was dealing with a sick infant in Gray’s Ferry. It’s not clear if William Temple had yellow fever, or if he had one of the other million things that killed infants in the 18th century. John Todd managed to get himself back to Gray’s Ferry, but died there on October 24. A few hours later, baby William Temple also died.

In the space of one month Dolley had lost her father-in-law, mother-in-law, husband, and infant child. It was dark days in Philadelphia in 1793. To this day, there’s no cure for yellow fever, only treatment of symptoms. But there is now a vaccine.

Mary Payne sent a letter to a family nurse, describing their situation:

“How shall I express my feelings, O it seems to me as if my heart would break; my Poor Dear Dolley, what does she and will she suffer. How distressing is her situation, the day she consigned her Dear husband and her little babe to the silent grave; she has no friend in town Nurse but thee to depend on; she is here among strangers and friendless; she is in debt for the burial of her babe and nearly moneyless, having only nineteen Dollars Left and a number of other Debts to pay before she can move, and we must go from this in a few days; pray, consider her Condition and if her poor Dear husband has left any money with thee contrive to send it to her; also if it is possible for thee to appoint a time and place we will try to meet thee; Dolley is very unwell and wishes… that she may get from this place.”

Soon after this letter, Dolley returned to Philadelphia with her mother, siblings, and surviving son. Mary Payne decided to sell her house in the city and move in with her 16-year-old daughter Lucy and Lucy’s 18-year-old husband, George Steptoe Washington. They had a rather grand plantation house in Virginia called Harewood that had been left to George by his father, Samuel Washington. With Mary went her two youngest children, Mary, age 12, and John, age 11. Her remaining unmarried daughter, 14-year-old Anna, stayed in Philadelphia with Dolley and young Payne Todd. They lived together in the house that John and Dolley had purchased not even three years earlier.

Anna and Dolley became almost inseparable, and Dolley looked after Anna as if she were her daughter. In fact, she often referred to Anna as her sister-daughter throughout their lives.

As if things weren’t hard enough for Dolley, after losing her husband, a child, and her in-laws to yellow fever, and her mother and siblings to relocation, she then had to fight her brother-in-law to get what was rightfully and lawfully hers under the terms of John Todd’s will.

In July 1793, before the epidemic began, John had made out a will. It was not only a legal document, but John included endearing language about Dolley as well:

“I give and devise all my estate, real and personal to the Dear Wife of my Bosom, and first and only Woman upon whom my all and only affections were placed, Dolley Payne Todd, her heirs and assigns forever, trusting that as she has proved an amiable and affectionate wife to her John, she may prove an affectionate mother to my little Payne and the sweet Babe with which she is now enciente. My last Prayer is may she educate him in ways of Honesty, tho’ he may be obliged to beg his Bread, remembering that will be better to him than a name and riches. Having a great opinion of Edward Burd and Edward Tilghman, Esquires, my dying request is that they will give such advice and assistance to my dear Wife as they shall think prudent with respect to the management and disposal of my very small Estate, and the settling of my unfinished business. I appoint my dear Wife executrix of this my will.”

Three things stand out from this will: 1) John very clearly loved and trusted his wife; 2) he was a Quaker through and through, believing that it was better to be honest and poor than rich and entitled; and 3) these people were weirdly squeamish about pregnancy. Using the French word “enceinte” instead of “pregnant” when referring to his and Dolley’s unborn child is a little weird. But whatever. 

The will couldn’t have been more clear that everything was to go to Dolley and young Payne, but somehow John’s brother James thought he could get away with denying Dolley what was legally hers. He could not have been more wrong.

Things started amicably enough, and Dolley had no reason to think that James would try to shut her out of what was legally hers. They had had a pleasant relationship during her nearly four-year marriage to John. She wrote to James and asked him to send her copies of John’s business accounts, and also a copy of their father’s will.

James’s response apparently does not survive, but it seems that he refused Dolley’s request, and also must have indicated that he intended to sell off all of John’s physical goods and assets, because Dolley replied to him, “I was hurt my dear Jamy that the Idea of [John’s] library should occur as a proper source for raising money—Books from which he wishes his child improved, shall remain sacred, and I would feel the pinching hand of Poverty before I disposed of them.”

After hearing nothing from James, Dolley wrote again, “I wrote thee some days ago requesting a copy of will & the papers contain’d in the Trunk. I hope friend West may be the bearer of them as it is highly improper that I should be without them.” Dolley knew what her rights were and she was prepared to exercise them.

James continued to stonewall her. In February 1794, Dolley sent another demand, this time by messenger: “As I have already suffered the most serious Inconvenience from the unnecessary Detention of my part of my mother in law’s property and of the Receipt Books and papers of my late Husband, I am constrained once more to request—and if a request is not sufficient—to demand that they be delivered this day—as I cannot wait thy return from this proposed Excursion without any material Injury to my affairs. The bearer waits for thy answer.”

Subtext: do not mess with me, bro. 

Dolley finally got fed up with waiting for James to do the right thing. So in classic American fashion, she sued him. Considering that her late husband had been a lawyer, he undoubtedly had many lawyer friends. Dolley hired one of them, William Wilkins, to sue James Todd on her behalf. Long story short: she won. She got everything, and James got nothing. Not only did she get everything of John’s that was legally hers, but she also successfully sued for her share of John’s dead parents’ estate. Because John Sr. died before John Jr. did, everything that the father left to the son was legally the son’s at the time of his death, despite the fact that he died just a couple of weeks after his father and his father’s will had not yet been probated. And because John Jr. left everything to Dolley, that meant that what John Sr. left to John Jr. was now legally Dolley’s. The moral of this story is, do not mess with lawyers, and do not mess with Dolley.

One other person who helped Dolley with support and legal advice during this legal wrangling was none other than Aaron Burr. Yeah, that Aaron Burr. He was a senator from New York, and he actually lived at Mary Payne’s Philadelphia boardinghouse, which is how Dolley met him. They became such close friends that when Dolley made out her own will in May 1794, she named Burr as guardian to her young son Payne. 

And she illustrated that Payne’s education was as important to her as it had been to her late husband, including in the will, “As the education of my son is to him and to me the most interesting of all earthly concerns, and far more important to his happiness and eminence in Life than the increase of his estate, I direct that no expense be spared to give him every advantage and improvement of which his Talents may be susceptible.”

Unfortunately, as young Payne grows up, his main talents will prove to be drinking, gambling, and gallivanting. And the Madisons will, indeed, spare no expense covering his debts incurred via these activities. But let’s not get ahead of ourselves.

Aaron Burr had another important role to play in Dolley’s life: matchmaker. He’s actually the one who introduced Dolley to her future husband, James Madison, which happened right around the same time she made out her will in May 1794.

So we’re going to hit pause on Dolley and spend the next two episodes on James Madison. I don’t usually devote an entire episode, let alone two, to the male half of our presidential couples, but as I said in episode 4.1, James did a lot of important things before he even met Dolley, and I don’t want to shortchange them, especially the Constitution.

Next week, we’ll cover James’s early life, the war years (again), and everything else he did leading up to the Constitutional Convention of 1787.

Thanks for listening to this episode. As always, it was produced by me, and the music is by Matt Dull. Please leave a rating or review of the podcast if your podcast player allows for it. Thanks!