Woolford views Delaware history from a new angle

By Laura Walter
Posted 2/16/23

It’s quite possible that the study of Delaware history is what keeps Sylvester “Syl” Woolford young. Born in 1943, his voice is still bright and energetic, and he always has a …

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Woolford views Delaware history from a new angle


It’s quite possible that the study of Delaware history is what keeps Sylvester “Syl” Woolford young. Born in 1943, his voice is still bright and energetic, and he always has a fascinating tale at the ready. But he lived and worked a full lifetime before even digging into history in his mid-60s and becoming a sought-after lecturer today.

“I’m 79 years young. I’m not senile yet! I am an accountant, not a historian. I didn’t get into history until I was 65 years old. It gets into your brain cells, if you’re storing new knowledge … so I’m using new places of the brain.”

Woolford was raised in a tight-knit Black community near Newark, went to school, witnessed integration, earned an MBA and retired from work. When the City of Newark published a broad 250-year history, Woolford didn’t see people mentioned like his grandmother, who held the highly respected position of school teacher in the 1890s (a big deal in the Black community).

Woolford realized he needed to learn the histories that were important to him so that he could shine a light on stories that weren’t being told.

“There’s a tremendous void in African American history: not only in having access to African American history in the general public and public libraries, for example, but it also hasn’t been researched,” he said.

“We are a very young country,” and Woolford is researching angles that “a lot folks just haven’t explored.” By examining incidents from another angle, Woolford pursues a more complete view of history, one that includes his ancestors’ experience. After all, genealogy research is one of today’s biggest hobbies.

“I come to this thing new, but it is a new level of consciousness that American history should not only record the history of the rich and powerful, but also talk about … indigenous people, Blacks and other ethnic groups that came to the United States.”

Now, his resume includes Delaware Heritage Commission; Wilmington University’s History Committee; University of Delaware guest speaker; Friends of the Delaware Public Archives; the Historic Preservation Fund; and the Delaware Chapter of the Afro-American Genealogical Society. In 2022, New Castle County proclaimed June 30, 2022, to be “Syl Woolford Day.”

Although he jokes that history work gives him something to do, Delawareans have taken notice of his storytelling, enthusiasm and expertise. He is a frequent guest lecturer statewide.

Speaking at Dover Public Library this month, he’ll discuss Brown v. Board of Education and all the information most folks don’t know about the landmark desegregation case—including that Delaware had its own lawsuits that were wrapped into the case working up to the Supreme Court.

“Since I was a kid, Brown v. Board has been Linda Brown in Topeka, Kansas, suing the board of Topeka to integrate the schools in Kansas. That’s the story, and you get an ‘A’ for that answer,” Woolford said. But actually, by the time it reached the Supreme Court, “Brown v. Board was the consolidation of seven different cases in five different states … there were actually two cases here in Delaware.”

Many of these were challenges simply demanding that Plessy v. Ferguson be upheld. “America was living under the delusion” that a separate education could be considered equal — so families of color started suing.

“These are the changes we need to make for a more equitable society,” Woolford mused. “Why should anybody come hear about something that happened 70 year ago? One reason is: you don’t know what happened 70 years ago, and sometimes the same stuff is happening now.”

Woolford estimates that he could offer different 400 lectures on various topics and angles. He especially loves finding old Black newspapers and publications. “Did the Black press focus on things that the white press didn’t? Yes, yes, yes,” he laughed.

“If you go back to the first newspaper, the 1827 Freedom’s Journal … you have an incredibly different view of history. I want to read the Black press because I want to hear what Black folks thought about America … and slavery.”

Here's one example of Woolford’s using old documents to reframe reality.

“I’ve been lecturing at the University of Delaware, and I accidently stumbled across something as I was doing my research.” Records say that less than 2,000 people were enslaved in Delaware ahead of the Civil War. But rather than lose cheap labor, Woolford said some slave owners delayed the official manumission. Instead of full freedom, they made the workers into an indentured servants—more work without pay. For instance, “If you give me another 20 years of indentured servitude, then you are free … There are documents of these [delayed] manumission papers. Then, if you showed up on the census in 1850, there were Black folks listed as ‘free,’ but still had another 10, 20 years until they were free, and it changes Delaware’s history books. There were only 1,600 slaves, but there could have been 2,000 to 5,000 Blacks who were indentured,” Woolford recently suggested to a class of PhD students. “Go back and read the census documents and these manumission papers. Go back and find out when they were really free.”

Syl Woolford presents “Brown vs. Board of Education” at Dover Public Library on Feb. 21 at 6 p.m.

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