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Tolliver was often mentioned in his local newspaper, the Shepherdstown Register, leaving a small trail of life events for historians to follow.
Shepherdstown Register, Chronicling America, Library of Congress.
On May 30, 1901, the Shepherdstown Register ran a short paragraph in its “Little Locals” column—where they featured “The Things of Interest that are Happening in Our Neighborhood and Elsewhere”—about the installation of several new telephones. “The telephone business is having a boom in Shepherdstown this week,” the paper noted. The Jefferson Savings Bank, A.S. Dandridge & Co., the episcopal reverend, a local attorney, and even the Register itself were visited by the Winchester Telephone Company.  In 1901, telephones were still a rarity in the United States; by 1904, there were still only 3.3 million telephones in the country for a population of approximately 76 million people.  To get a telephone back then meant you had money to spare and a good reason to be placing a lot of calls. Only eight people in Shepherdstown had the means at that time, including a man named J. M. Toliver.
James Madison Tolliver (also spelled Toliver and Tolivar at various times), more often called Mat, was a local entrepreneur. Between the 1880s and 1910s, he ran a range of successful businesses—including a hotel, restaurant, grocery, ice delivery, and livery businesses—as well as operated a small farm. These ventures were quite successful. The Produce Reporter Company’s Blue Book gave him a high credit rating, indicating that Tolliver had good relationships with wholesalers, paying them promptly and in full for the groceries and goods they supplied for his retail operations.  In 1903, the Register reported that Tolliver was one of three Shepherdstown grocers to purchase computing scales, “ingenious devices which do the calculation for the salesman and do it so well that no mistake can be made.” Like the telephone, the computing scale was a relatively new technology; you couldn’t buy one before 1891.  And in 1912, only four years after the invention of the Model T Ford, Tolliver appeared once more in the newspaper for being an early adopter of the latest innovation; he was the first African American man in his section of Shepherdstown to own a car. 
Mat Tolliver was born around 1850 in Rockingham County, Virginia. By 1873, he had moved to West Virginia and fallen in love with a local Shepherdstown woman named Hettie Ross.  Ross—who was about a year younger than Tolliver—lived with her mother and three sisters at the Entler Hotel; her mother, Ann, worked as the hotel's cook, and Hettie and her older sister, Sallie, were chamber maids. It is unclear whether Tolliver or the Rosses were born enslaved; there were small populations of freedmen in both Rockingham and Jefferson counties, but the enslaved population was significantly larger.  However, Mat and Hettie's 10 children were born undeniably free; the first, William, was born a year after they married. 
In these early years of their life together, Mat worked as a laborer, and Hettie kept house and cared for the children. In 1887, he opened an oyster business and restaurant above a local store. There, he sold oysters “by the pint, quart or gallon, or by the plate cooked any style,” and even offered delivery. The business clearly did well, because in 1890, Tolliver rented a large brick building where he could operate the restaurant and also run a hotel. 
For every step forward, there were setbacks; for example, a fire burned through the hotel in 1892, though the building was saved.  The next year, Tolliver moved his hotel and restaurant to this property at 109-11 S Princess Street, which he bought for $2,000—almost $600,000 in 2021 dollars—and at some point he started a livery business, renting horses and carriages. Alas, another fire broke out in 1894, this time burning the Princess Street building to the ground. The Register reported: “Tolliver succeeded in saving all the stock of groceries in the store and an organ with some little furniture that was on the first floor,” but lost “about $60 in cash, two gold watches valued at $75 and nearly all of his household effects.” Luckily, Tolliver had insured the house and furniture for $1,500—one more indication that, at least financially, he was doing well.   Three weeks later, under the headline “Another Improvement,” the Register ran a short article about Tolliver’s plans to rebuild. Tolliver’s “handsome new structure on the old site”—which is what exists today—was 3,100 square feet, with a ground-floor retail space, “three rooms for [the] restaurant” and six rooms upstairs.  From this new building, Tolliver continued with his restaurant, grocery and livery businesses, and added an ice house and ice cream parlor to his portfolio of ventures. 
While business thrived, the family experienced tragic losses. The Tolliver’s oldest son died of tuberculosis in 1889; he was 15 years old.  Then their son John stabbed another man and was sentenced to prison in 1897.  Mat's sister died in 1904, and John died only two months later of tuberculosis at 25 years of age. Tuberculosis also consumed 24-year-old Jerry (1907) and 30-year-old Lucinda (1908). 
When Tolliver died, also of consumption, in 1917, the Register published a moving tribute, honoring “Uncle Mat’s” legacy as a businessman and a man of exemplary character, honesty and dependability. His funeral was well attended by both Black and white people from the community. 
In some ways, Tolliver’s life was ordinary for a man in a southern state in the late 19th and early 20th centuries. Although his entrepreneurial success and commitment to civic life earned him great respect, Tolliver’s race was always a factor. He was often referred to in the paper as “colored,” and in that way he was constantly marked as other. Also, like many American families in these years, misfortunes like fire and illness struck with heartbreaking regularity. Regardless, at a time when millions of descendants of former slaves were moving northward to escape the indignity and violence of Jim Crow, Tolliver overcame great challenges and odds to carve out a successful space for himself among Shepherdstown’s business class.
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