Simmie Knox and Randy Holland: A relationship woven at a woolen mill in Milford, Delaware

In 1959, my dad was 12 year old. My grandfather was the cafeteria manager at a woolen mill in Milford, DE. A young man named Simmie Knox worked there and offered to paint portraits as a way to earn money and practice his art. My grandfather took him up on it, and for my entire childhood a portrait of my dad as a 12 year old, along with another of his brother, hung proudly on the walls of my grandparents’ house on NW 2nd street in Milford.

In high school, my dad and my uncle also worked at the same textile factory. It was tough work at a woolen mill in the summer. I grew up hearing stories of the dust from the wool swirling in the heat, allergies, humidity, and heavy machinery. The experience was so impactful, that Dad kept his commercial truck endorsement active on his driver’s license his entire life.

Simmie went on to the Tyler School of Art and began painting portraits professionally. Over the years, his portfolio placed him among the top of his craft. He’s painted Hank Aaron, Mohammad Ali, Oprah, the Clintons, Thurgood Marshall, David Dinkins… the list is incredible.

Almost 50 years after the first portrait of my dad, Mr. Knox painted a second portrait – this time for dad’s appointment to the Delaware Supreme Court.

In this portrait, dad asked to include his wedding ring, his Lincoln’s Inn tie, his book on the Delaware constitution, and a family photo. I wore the same tie when I have his eulogy.

As one of only a half-dozen black students at the school, Knox recalled feeling isolated in the dining hall, ignored by white students.

“Every now and then, some brave soul followed the courage of conviction,” he says.

While attending school and working at a textile factory in Milford, Del., he painted an 11-year-old Randy Holland at the request of Holland’s father, who worked with Knox at the factory. Nearly a half-century later, Holland returned the favor by asking Knox to paint his portrait when he was appointed to the Delaware Supreme Court.

USA Today: “Artist Simmie Knox captures spirit of trailblazers”

Dad with Simmie in 2007, standing with both portraits.
Photo credit: The News Journal/William Bretzger

When Justice Ginsburg died, dad wrote an article for the Delaware State Bar Association which brought the three of them together:

I knew that Justice Ginsburg had her portrait painted by the renowned
artist, Simmie Knox. I wrote to her that he was also going to paint my
portrait. I told her that he was a longtime family friend who had previously painted my portrait when I was a teenager and he was a college
student with no training. She was happy to hear my story about Simmie.
She wrote that she appreciated his talent in portraying her, after a recent
illness, “as I hoped I would be after my health and strength were restored.”

-Randy J. Holland

After my dad died, I found two letters from Justice Ginsburg to my dad about Mr. Knox’s work.

What an amazing shared connection. Two men from humble beginnings, who met at a woolen mill in Milford, followed their hearts, never quit, and fulfilled their dreams.

Simmie Knox’s iconic signature on his portrait of Randy Holland

One response to “Simmie Knox and Randy Holland: A relationship woven at a woolen mill in Milford, Delaware”

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