Jonathan Jessop the Man Behind "The Cut"

The stories below are just a brief summary of a true renaissance man who led a remarkable life and deserved to be well-remembered.

From North Carolina to York, Pennsylvania

Jonathan Jessop, the namesake of Jessup, Maryland, led an extraordinary life that spanned from his beginnings in Guilford County, North Carolina, to becoming a key figure in York, Pennsylvania. While G. Marie Biggs’ The Story of Jessup (1977) gives him a brief mention as a contractor, much of his rich personal history is missing. Jessop was much more than just a name connected to a town—he played important roles in his community, business, and social causes, particularly the anti-slavery movement.

Jessop was born on September 30, 1770, to Ann Matthews and Thomas Jessop, a well-known Quaker preacher. In 1781, the famous Battle of Guilford Courthouse in North Carolina was fought on his father's land.  Jessop actually drew a map of the battlefield (see image).  Following his father’s death, his mother relocated the family to York, Pennsylvania, where they joined her cousin, Elisha Kirk, a clockmaker and Quaker minister. Jessop became Kirk’s apprentice and, after Kirk’s death in 1790, took over the business.

In 1794, Jessop married Susanna Updegraff, the daughter of Joseph Updegraff, one of York’s founders and a prominent figure in the York Society of Friends (Quakers). Jonathan and Susanna had six children, and their eldest, Joseph, worked with his father in the clockmaking trade. Their daughter, Mary Ann, married into a family that would become involved in the abolitionist movement—a cause close to Jonathan's heart.

A Man of Many Roles

Clockmaking was more than just a profession for Jessop; it was also an entry point into the world of engineering. Jessop's most famous apprentice, Phineas Davis, went on to build the first coal-burning steam engine used by the Baltimore & Ohio (B&O) Railroad. Jessop’s involvement with York extended beyond his business—he played a central role in the town's civic life. He helped repair York’s fire engines and served as president of the fire company, later known as the York Vigilant Fire Company.

Jessop's commitment to civic service also included his long-standing position as clerk of the York Meeting of Friends, starting in 1797. He was deeply involved in public service as well. In 1800, Jessop became one of York’s assistant Burgesses and later held the position of Burgess (mayor-like position). Additionally, he managed the local almshouse, a home for the poor, and played roles in the York Bank and the York Public Library.

His moral and social views were aligned with his Quaker beliefs. The Friends Intelligencer reported on his moral character, noting that "he remained free from prejudice, always striving for peace and fairness within his community." This attitude carried through in all his civic and professional engagements, and it also extended into his passion for public service.

Engineering Projects Before the B&O

Before his involvement with the B&O Railroad, Jessop had already built a reputation as an engineer. In 1809, he became the superintendent of the York and Conewago Turnpike, working to connect York to its surrounding regions. In 1811, Jessop and a business partner, Michael Gardner, patented the “Balance Bridge,” a design noted for its ability to span large rivers. The patent described the bridge as being "particularly adapted to large spans, from one hundred to three hundred feet" and praised for its durability and simplicity. This invention underscored Jessop’s engineering acumen, and he and Gardner produced these bridges in their iron foundry.

A New Beginning in Horticulture

In 1817, Jessop’s cotton business and clockmaking workshop were devastated by a flood in York. While many businesses might have folded under such hardship, Jessop managed to rebuild. He eventually handed over the clockmaking business to his son, Joseph, in 1823. Free from the demands of that business, Jessop turned his attention to horticulture, another one of his passions.

In 1820, Jessop discovered and propagated what would eventually be called the York Imperial Apple. Originally named "Jonathan’s Fine Winter" because of its long-lasting qualities, the apple was popular for its ability to survive the winter months without spoiling. In 1855, New York pomologist Charles Downing renamed it the "York Imperial" to reflect both its origin and its superior quality. The apple quickly gained popularity, and even today, York Imperial apples are still grown and enjoyed. In 1926, the Pennsylvania Farmer recognized Jessop as "a figure as important to Pennsylvania’s apple industry as Johnny Appleseed."

Jessop’s Role with the B&O Railroad

Jessop’s contributions to the B&O Railroad were also significant. After the success of the Tom Thumb in 1830, the B&O Railroad sought to create a more powerful steam engine to carry freight and passengers. Jessop’s former apprentice, Phineas Davis, answered the call and designed "The York," the first coal-burning engine used by the railroad. Davis’s engine was described as a "grasshopper-style" engine, and its success led to further work with the B&O, where Davis became the head of the Motive Power Department until his death in 1835.

Following Davis’s death, Jessop was appointed Superintendent of Machinery for the B&O Railroad, a role that placed him in charge of the construction and maintenance of engines and cars. His duties included overseeing water stations, depots, and ensuring that the engines were always ready for service. He held this role until 1839 and played a vital part in keeping the railroad running smoothly during its critical early years.

Abolition and the Underground Railroad

There is ample evidence to suggest that Jonathan Jessop and his family were involved in the abolitionist movement. His grandson, Edward Chalfant, was said to distribute abolitionist literature and provide food to freedom seekers passing through the area. Additionally, Jessop’s son-in-law, James Chalfant, reportedly transported fugitives to Amos Griest, a known abolitionist and Quaker leader in York.

York, Pennsylvania, was a key stop on the Underground Railroad, and many Quakers played an active role in aiding enslaved individuals seeking freedom. According to William Still’s The Underground Railroad, York residents like Joel Fisher and Samuel Willis were instrumental in helping freedom seekers escape. These men were close associates of Jessop, and their abolitionist activities further suggest that Jessop himself was involved, even if indirectly.

One particularly compelling piece of evidence is a letter written by Yardley Taylor, a prominent abolitionist from Loudoun County, Virginia. Taylor wrote to Jessop, asking for his help with an enslaved man named Harry who was trying to escape. Taylor’s letter requested that Jessop provide Harry with a "safe private conveyance" and detailed the route Harry should take to freedom. Although Harry was captured, Taylor’s appeal to Jessop underscores the trust that existed between abolitionists and the important role Jessop likely played.

York Meeting House and the Testimony Against Slavery

The York Meeting of Friends consistently expressed their opposition to slavery. In their meeting minutes from August 1842, the Friends noted: "Our testimony against slavery is maintained." By the 1850s, the minutes recorded that African Americans under the care of the York Meeting were "provided for" and "instructed in useful learning," showing a commitment to ensuring that those who had escaped slavery were given the opportunity to succeed in their new lives.

These meeting records, combined with Jessop’s close relationships with known abolitionists like Joel Fisher and Samuel Willis, suggest that Jessop, while perhaps not a public figure in the movement, quietly supported the cause.

A Lasting Legacy

Jonathan Jessop’s life was marked by his wide range of talents and contributions. From clockmaking and engineering to horticulture and civic leadership, Jessop left an indelible mark on York, Pennsylvania. His involvement with the B&O Railroad and his role in developing the York Imperial Apple are two of the most prominent aspects of his legacy, but his quiet contributions to the abolitionist movement are equally important.

Jessop was remembered in his 1857 obituary as a man of "genial disposition" and "freedom from prejudice." The obituary further praised his character, stating, "He lived far beyond the age granted to most men, and did so without making a single enemy."

Whether through his work as a clockmaker, his invention of the York Imperial Apple, or his involvement in the fight against slavery, Jonathan Jessop was a man of integrity and dedication. His legacy continues to inspire, reminding us of the power of moral conviction and community action in the face of injustice.

[A more complete story, with full sources and citations, will appear in our next local history book.  In the meantime, feel to contact us about Jonathan Jessop].