+ By Christine Fillat + Photos by Karen Davies

“Pee Wee” Reese was a National League baseball shortstop who played for the storied Brooklyn Dodgers in the 1940s. While he was captain of the team, Harold Henry Reese was best known for publicly embracing a friendship with Jackie Robinson in front of racist baseball fans. He was a true team player.
The same may be said of Matthew Reese, another “Pee Wee.” Reese is the owner of Blk Ankr Originals, a screen printing shop in the Annapolis Design District, where he custom prints T-shirts, garments, and posters. His actions during Annapolis’ trying times reflect the size of his heart, which is quite large, much like his stature. “I am often the biggest person in the room,” he muses.
Reese was director of marketing for a safety equipment distributor, where he worked for 15 years, during which he struck up a friendship with Frankie Orange of Orange Tattoo Company and Orange Screen Printing. When Orange’s screen printing shop was put up for sale, Reese’s creative juices started flowing. He had an interest in screen printing that went back to high school and had earned a visual communications degree from Towson University. The time seemed right for a career change. He bought the business in 2012, renamed it Blk Ankr, and operated in the back of Orange Tattoo Company. In 2013, he moved to his present location on George Avenue.
Reese knows artist Jeff Huntington, who also has a screen printing business, through Huntington’s brother Joe, who was also at Towson. Through Huntington, Reese met Jimi Davies (Up.St.ART Annapolis’ publisher). “That’s when I started with people, through [Orange and Davies and Huntington], just doing jobs for local businesses. I started making all these local connections. It’s a fun part of the business, getting to know a lot of the local players. Just being at the tattoo shop, you tend to meet a lot of local people.”

Chris Bless and Grayson Reese work on a T-shirt order. Photo by Karen Davies.


“Look Great, Feel Great, Do Great Things” is Blk Ankr’s motto. Looking great will help in feeling great, which is what Reese aims to do by producing excellent products. Doing great things is something that seems to come naturally to Reese. Says Huntington of Reese, “[He’s] a passionate artist who cares about the quality of work he generates into the world. Some artists work to continually improve and raise the bar higher and higher. He is one of those.”
When Sailor Oyster Bar in Annapolis suffered a devastating fire in June 2022, Blk Ankr teamed up with Heroes Pub to sell T-shirts as a fundraiser. With “Don’t Give Up the Ship” on the front, the shirts sold for $20, with $15 going to the restaurant. “I think we raised $7,000 for them,” says Reese. In the aftermath of the Capital Gazette shootings in 2018, artist and musician Aaron Yealdhall (aka Skribe) designed his “Press On Annapolis” logo for a T-shirt fundraiser, and Blk Ankr printed the shirts.
“Start where you are, use what you have, do what you can” is part of an Arthur Ashe quote that served Reese well during the onset of the COVID-19 pandemic. In March 2020, Reese saw his business evaporate before his eyes. Three jobs that were being prepared for print were canceled. He watched as small businesses all around him were ordered shuttered. Looking to the internet for some inspiration as to how other businesses were handling the shutdown, Reese noted a screen printer in Canada who put forth the concept of a partnership with local businesses. After gaining permission to replicate the idea, “Stronger Together” was born.

Reese lines up a silk screen shirt print. Photo by Karen Davies.


Reese set up a website selling shirts for local businesses, offering a gray shirt with black print and a black shirt with gray print. All the shirts, with the phrase “Stronger Together” on the sleeve and a custom-designed graphic on the front, were sold to the public for $20. For every shirt sold, the businesses received $10, and Blk Ankr used the remaining $10 to buy the blanks, to print the shirts, and for packaging.
The effort started with six companies, and by the time it ended, nearly 100 businesses were involved. Some companies sold only a few shirts, others sold hundreds. Everyone made some money. “We sold around 3,300 shirts. We put about $30,000 out to local businesses,” says Reese. “We sent shirts out all over the country and all over the world . . .
We sent shirts to [maybe] 37 of the 50 states.”
“He jumped into action, facing uncertainty like everyone else, and utilized his artistic skill sets and positive messaging to help lift other small businesses, not only in his community but worldwide,” says Huntington of Reese during that time. “To me, this is about maximizing the positive forces of art and one’s creative abilities. And through his innovative and compassionate individual efforts, Pee Wee created a big ripple across the pond.”

One of the “Stronger Together” shirts. Photo by Karen Davies.


Reese has a rescue Doberman pinscher, Renfield, named after Count Dracula’s devoted servant. But Reese is not secretly Dracula; actually, he is Santa Claus. His wife, Jennifer, is assistant principal at Central Special School in Edgewater. One winter, around 2016, she needed a Santa Claus for a school program and “voluntold” Reese to fill in. He liked the gig so much that he reprises the role every year. He has his own suit and accessories, and to appear more authentic, he lightens his beard and hair at his cousin’s hair salon. He adheres to the unwritten rules of appearing as Santa Claus. “In the Santa community, it is a responsibility to maintain this legend of Santa Claus,” he says. “When you see a kid who thinks you’re Santa Claus, they light up. They smile. It’s fun.”
He says it’s the one time of year when he’s always thinking about how to prepare for it. “Hopefully, this year, I’ll do some more [Santa Claus] gigs,” he says. “Hopefully, my one gig will turn into two, and the two will turn into three, and then maybe, by the time I retire, I’ll just be Santa Claus. That’s the only retirement plan I have right now.” 