Upon his arrival to the United States from England in 1819 Henry Shaw initially questioned its benefit. He expressed his thoughts at the time in an 1820 letter to his mother in regards to the heated national debate about Missouri entering into the Union as a slave state. “The present session of Congress of the United States have admitted Missouri in the Union as a slave state, whether slavery will be a benefit to the country is doubtful.” Slavery at the time was considered an economic institution in the southern states and Missouri, admitted to the Union in 1821 as a slave state was no exception. While a merchant in St. Louis Shaw apparently had a change of opinion on the subject. The earliest mention of the subject of slavery in the Shaw papers is in 1824 where a purchase of "linen cloth for Negro clothing" is found. The earliest existing record in the collection of the purchase of an enslaved person by Shaw is Peach in 1828. By 1850, census records indicate Shaw owned nine enslaved people and we know that by 1853 that number had grown to eleven. 1860 census records show eight enslaved persons. While we lack detailed accounts of these enslaved people lives and the work they were forced to undertake their tasks could have included farm hands, maids, servants, and cooks and archival records indicate Shaw hired out them out to others. In the years 1854 and 1855, enslaved persons under Shaw's ownership escaped and bounty hunters, notably those of Benard Lynch, were hired to return them. Enslaved person, Sarah, whom Shaw purchased in 1850 along with her infant child made her bid for freedom in May of 1854. In response, bounty hunters hired by Shaw tracked Sarah to Chicago and returned her to St. Louis in 1855 at which time she was subsequently sold. Another escape attempt occurred in the early morning of May 21, 1855. Nine enslaved persons including four owned by Shaw; Esther, her two children, and one unnamed male made their break for freedom utilizing the Underground Railroad with the assistance of Mary Meachum; herself a former enslaved person. They attempted crossing the Mississippi River to Illinois; bounty hunters awaited them and they were soon captured and Mary Meachum would be jailed. Esther too would be sold by Shaw as a result of her escape attempt. The location of this historic event on the banks of Mississippi River north of downtown St. Louis is today memorialized as the Mary Meachum Freedom Crossing. Other enslaved persons documented in the Henry Shaw Papers include Bridgette, Jim, Joseph, Juliette, Tabitha and her daughter Sarah, and unnamed women and children. Existing archival records last show enslaved persons in Shaw's 1855 taxes; they are listed under property as was customary of the time. However, U.S. census records list eight people enslaved by Shaw in 1860 — seven women and girls ranging in age from four to 50 years old, and one 12-year-old boy. As with the 1850 census, their names were not listed. Unfortunately no papers exist in the collection where Shaw reflects on his participation in the institution of slavery or of the American Civil War.