Hannah and Billy

Billy Penn’s clingy love letters, romantic treason: Tales of colonial Philadelphia love

Philadelphia’s founders did things like settle the city, invent electricity and *maybe* sew the first American flag. They were also just looking for love. And for Valentine’s Day, Billy Penn has recounted four stories of founders’ romance. Cindy Little, historian at the Philadelphia History Museum, provided background on these tales of love.

William and Hannah Penn

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The founder of Philadelphia married up. After Billy Penn’s first wife died, he set his sights on Hannah Callowhill (yep, the street is named after her). You’d think a guy who founded a colony and whose statue would later adorn the top of City Hall would be a magnet for the ladies, but they could likely see his desperation.

“He was bringing children from the first marriage and probably not the most attractive guy in the world but prominent,” Little said. “He wanted and needed to be in couple.”

Hannah, in particular, presented a challenge. She was a skilled accountant and business manager. To prove his worth, Billy wrote her a series of letters that didn’t so much read like proclamations of love but persuasive arguments that she should be with him. He made a lot of creepy mistakes in these letters: He was clingy, writing twice as many letters as she did and starting some of his letters with passive-aggressive reminders that she hadn’t responded, like “Indeed I cannot, if I would, reproach my dearest friend for a careless silence.” He also could have easily ended up in the friendzone, starting some of these letters with the phrase, “For My Dearest Friend.”

Apparently his logic and persistence worked, though. They got married — she was half his age — and had eight kids. She outlived Billy by eight years and took over his work as the unofficial governor of Pennsylvania. The state honored her in 2014 by hanging her portrait among the portraits of Pennsylvania’s other governors at the statehouse.

Ben and Deborah Franklin 

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You’ve heard all the stories about Franklin’s shenanigans in Paris. But before he was behaving like a bachelor overseas, he married to Deborah Read Franklin, who came from a prominent Philadelphia family. Their marriage began at great risk. When they fell in love Deborah was married to another man — the marriage had been “a rebound thing,” Little said — who had disappeared. If he ever returned and Benny and Deborah were together, they could have been publicly shamed and whipped. Luckily, he never did, and the Franklins stayed together for decades until Deborah’s death in 1774. She played a crucial role in Ben’s business, signing contracts and keeping track of finances while he traveled in England.

Betsy Ross and John Claypoole 

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Ross was married three times. Her first husband, John Ross, died in accident, likely an explosion at an arsenal he was guarding. Her second husband, John Ashburn, fought in the Revolutionary War and got captured by the British. He died overseas in prison, and a fellow prisoner, Claypoole, came back to explain what happened to Ross.

“Lo and behold a romance is struck up,” Little said.

They got married and had five daughters together.

Peggy Shippen and Benedict Arnold 

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It’s the typical love story: Girl meets boy. Dad disapproves of boy because he’s British. Girl marries other boy who’s twice her age so she can foster a relationship between him and the first boy that leads to the most infamous case of treason in United States history.

This, more or less, is what happened with Shippen, who grew up in Philadelphia high society as the daughter of a judge and great-granddaughter of Princeton University’s founder. Shippen fell in love with a British officer named John Andre in the late 1770s when Philadelphia was under British occupation. Her father wasn’t having it, and Shippen, 19, obliged, marrying Benedict Arnold, then 37, shortly after. Andre and Arnold got to know each other through Shippen. Arnold had been put in control of West Point, then a prominent military fort, and in 1780 Arnold and Andre hatched a plot to give control of the fort to Andre and the British. After getting caught, Andre was executed and Arnold escaped to the enemy’s side. Shippen and Arnold later fled to Britain.

Little is scheduled to give a talk about Philadelphia power couples at the museum on March 21, focusing on the women as part of Women’s History Month.

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