Holding Court

Neighborhood café has new owners, same spirit

For the past twelve years, Jester’s has been a cornerstone of Castle Street, first as Jester’s Java and for the past eight years as JESTER’S CAFÉ. The cozy green cottage exudes Southern hospitality, and guests are greeted at the door with welcome.

Founders Jamie Thomasson and Steven Fox announced the sale of the business in December to Robert Powers and Sydney Penny (left), longtime friends and Jester’s customers since the eatery’s opening.

“When Jamie confided that he was interested in selling, we figured we had better buy it to make sure it wouldn’t change too much,” Penny says.

Penny and Powers describe Jester’s as their second home, the place they’ve been coming since they first arrived in Wilmington in 2005. It was where they met their friends and neighbors, where they went to find out what was going on around town.

“We found ourselves there sometimes for hours because there was always someone to talk to,” Penny says. “We wouldn’t have wanted someone to come in and change it drastically because we’ve loved it for all this time. There’s just a character that has to remain.”

Once Powers and Penny made their interests know to Thomasson and Fox, Powers began working with Thomasson in the kitchen. Both were interested in seeing if it was the right fit.

Powers, an artist and Le Cordon Bleu-trained chef, spent a year-and-a-half working alongside Thomasson to learn the particulars of both the kitchen and the business prior to the sale being finalized.

While Powers and Penny have updated Jester’s three small dining rooms with new paint and artwork, including artwork by Powers and other local artists, they have made very few changes to the menu.

Brunch specialties include a black bean benedict with tomato, avocado, and hollandaise; French toast casserole; and a strata with sausage, cheddar cheese, and hash browns.

Quiche is the number one seller at lunchtime, and Powers prepares both a meat and a vegetarian quiche daily. Homemade soups such as chicken and pastry, gumbo, and white bean chili are prepared daily, as well desserts like chocolate peanut butter and key lime pie.

Other popular lunch items include the shrimp salad, the Cobb salad, and the Castle Street club with roast beef, turkey, bacon, provolone, and cheddar on toasted rye.

Many regulars have their favorite go-to menu items, but Powers enjoys creating daily specials to give patrons the option to try something new.

Whole quiche is available as well as sides and salads by the pound and soup by the quart.

Jester’s open kitchen gives diners in the back room a view of the action taking place behind the scenes. It’s a small kitchen, barely large enough for Powers and his crew. They have to keep their voices down to avoid being heard by the diners, but the buzz of the busy kitchen just adds to the feeling of eating at someone’s home.

Powers says he and Penny, an actress who has appeared in numerous films and television productions, had thrown around the idea of opening a restaurant for years but probably never would have taken the leap without the help of Thomasson and Fox.

Penny jokes that she may be the only actor who never waited a table until she owned a restaurant.  “I’ve finally arrived,” she says. “All actors should have to be in the service industry at some point.”  

Perhaps one of the biggest parts of the service industry is connecting with customers. At a neighborhood café like Jester’s, customers are often regulars, and they enjoy the comfort of knowing they’re in good hands.

“People don’t like change and transition,” says Jester's new co-owner Sydney Penny. “So, you do have to prove yourself and do everything you can so that people feel comfortable and special.”

For Powers and Penny, that means getting to know those longtime customers they didn’t know already and building relationships with every new person that comes through the door. They say while there are definitely loyal customers, there are always new faces.

“Jester’s is a gathering space for an eclectic mix of people – that’s the way it’s always been,” Powers says, “just on the edge of everything.”

Much like their predecessors, Powers and Penny plan to be active in the ongoing revitalization of Castle Street.

Penny credits the Downtown Business Alliance and the Castle Street Business Alliance as having been vital in the efforts to bring new business to this part of downtown.

“We’re hopeful that we will see some of the growth that the north side of town has seen,” Penny says. “We’d love to see more people living and working on Castle Street.”


To view more of photographer Erik Maasch's work, visit ejmphotography.org.