This photograph of Henry Weil was most likely taken around the time of Gertrude's parents' marriage in 1875. Like many German Jews, Henry Weil's family immigrated to the United States to escape the economic disruption and rise in anti-Semitism that occurred following the European Revolutions of 1848. Although Gertrude's grandfather, Jacob, was able to earn a good living as an antiques merchant in Oberdorf, Germany, his sons were treated poorly by other children, and the future appeared brighter in America. Two married daughters, Bertha and Jeanette, settled in Baltimore, followed over the years by Herman, Henry and Solomon, and finally by Jacob and his wife Jette.

Herman was the first to go South, clerking in the store of a fellow German Jew in Goldsboro, NC. After Henry arrived in 1860 at the age of 14, the brothers made a living peddling. By the time the Civil War began, Herman felt so much a part of the community that he volunteered to serve in the Confederate army, becoming one of approximately 10,000 Jews to do so.

In the aftermath of the Civil War, Herman and Henry—joined by their youngest brother Solomon—took advantage of the need for new economic enterprises. Following a common path for Jewish immigrants in the South, they opened their own dry goods store. Their determination, ability and reputation for honesty and fair dealing—coupled with the fact that they filled a much-needed economic niche—quickly turned the shop into a substantial department store. Advertised as "H. Weil and Bros.—Who Do What They Say," the store became a trading center for much of eastern North Carolina, and the brothers expanded their ventures to include brick yards, coal yards, real estate, insurance, the Goldsboro Ice Company, the Carolina Rice Mill, and the Building and Loan Association. For two decades, a Weil was among the incorporators of any new business in Goldsboro. All three brothers married and settled in the area, making the family a significant influence in the region.