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In 1801 John Jay retired from public life to his farm in Bedford, New York.  The property was a sprawling country estate, around 700 acres.  While the farm was managed by a separate staff, the day-to-day household and estate operations were overseen by John Jay and his daughter Nancy.  In reviewing his account books, Jay seems to have had one man who was his go-to-guy for any type of job.  That man was Chester Tillotson.  In Jay’s ledger Chester is mentioned over 50 times between 1813 and 1817. These entries have to do with deliveries, payments, and even Chester’s salary. He clearly was a trusted employee. But there is one entry, dated February 4, 1813, that was life changing for Chester.  It reads: “Chester Tillotson a free black man in my service, To cash paid by his desire to Launcelot G. McDonald in part of the $100 for which he sold to Chester, his son also called Chester, of 9 years of age- $49.78.” In essence, John Jay gave or loaned Chester Sr. The funds needed to purchase his son out of enslavement.

How and when Chester Tillotson came to work for John Jay is unknown. He resided at Bedford House and worked there until at least 1820.  Having never been mentioned by name on any federal or state documents currently available to researchers, it is impossible to know what Chester’s life was like before he worked at Bedford House, or what his life was like after.

We do however know a little more about his son, Chester Jr. Born around 1804, Chester Jr. began his life as the property of James McDonald of Bedford.  The identity of Chester Jr.’s mother is unknown, but she was likely enslaved by the McDonald family at the time of his birth.  In 1800 the McDonald family is recorded as enslaving four individuals, with James McDonald listed as the head of the household.  Census data at the time did not collect the age or sex of the enslaved.

Letters in the Jay Papers at Columbia University indicate that John Jay knew James McDonald, and they corresponded in 1804 and 1805.  There is no mention of James after that, but by the 1820 census, Lancelot is listed as the head of the McDonald household. We can conclude that sometime between 1805 and 1813 James McDonald died, leaving his oldest living son to inherit his property, which included Chester Jr.

Once freed, Chester Jr. likely worked alongside his father doing odd jobs and working as a courier for the Jay family. How long Chester and Chester Jr. stayed at Bedford House is unknown.  They are both recorded on the 1820 census but were no longer living there in 1830.

By 1840 Chester Jr. was approximately 36 years old and was living in North Salem, New York. He is listed as the head of his household in the census that year.  There was also a boy aged 10-24 (George), a girl under 10, and a woman aged 36-55 who are residing with him.  There is no mention of Chester Sr.

In 1855 the State of New York conducted a state census. By this time Chester Jr. had moved to New York City and was living in part of modern-day Washington Heights. He and his son George moved there in 1846.  Chester was listed as being 55 years old and employed as a laborer.  Living with Chester Jr. were his wife Lucy Ann, George, his brother-in-law, and his brother-in-law’s wife.  Chester Jr.’s first wife, whose name we do not know, had died, and he remarried Lucy Ann, who herself was a widow.  Lucy Ann was only four years older than Chester Jr.’s son George.  It is unknown what happened to the girl under 10 listed in the 1840 census.

Lucy Ann is listed as being the owner of the land that their home was on.  At the time the house was valued at $700.  Both Lucy Ann and George knew how to read; Chester Jr. never learned.  It is interesting to note that Chester Jr. is the only person recorded as black in his neighborhood.  By 1855, a third of the 12th Ward where the Tillotsons resided was made up of Irish immigrants. Most other residents were European immigrants or working-class, white New Yorkers. The census taker listed both Lucy Ann and George as mulatto. Their ethnic make-up and ancestry are unknown.

Chester Tillotson gave his son the ultimate gift: freedom.  Using the relationship he had cultivated over many years of working for John Jay, Chester was able to secure the means to give his son a future.  Chester Jr. worked hard as a laborer, owned property, and built an even better life for his son.