Chef Robbie Jester Kitty Knight Deep Blue

Robbie Jester aims to infuse new life into Kitty Knight

Pam GeorgeCulture, Headlines

Chef Robbie JesterKitty Knight Deep Blue

Chef Robbie Jester is following in his father’s footsteps by going to work at Deep Blue at Kitty Knight in Galena, Maryland, Jester’s hometown.

Robbie Jester has come home. 

Sort of.

Raised in Galena, Maryland, the chef is partnering with Jamestown Hospitality Group, owner of Deep Blue at Kitty Knight, an inn and restaurant in Galena, to infuse new life into the old establishment.

Chef Robbie Jester Kitty Knight Deep Blue

Robbie Jester

“Ironically, my dad owned Kitty Knight in the 1980s, and I was conceived there,” said Jester, a Culinary Institute of America graduate. 

If Jester’s name sounds familiar, it’s because the skilled chef won the grand prize on Netflix’s “Pressure Cooker” series.

He also successfully competed on “Guy’s Grocery Games” and “Beat Bobby Flay.”

On May 28, he will join the “Chopped Battle Italiano” contestants.

Even if you haven’t watched the shows, you’ve likely tasted his food when he worked at Piccolina Toscana, the Stone Balloon Ale House or Limestone BBQ & Bourbon. He is also the owner of Pizzeria Mariana in Newark.

Kitty Knight: An Icon

Jester and Paul Bouchard, Jamestown’s chief operating officer, met while working at Toscana. 

“We’ve always kept in touch,” said Bouchard, who oversees Jamestown’s impressive portfolio, including Tonic Seafood & Steak in downtown Wilmington, Park Café in Wawaset Park, and Giordano’s in Kennett Square. 

The hospitality group purchased Kitty Knight in 2021 and changed the name to Deep Blue after Tonic’s predecessor. Bouchard had always loved the name, which suited the Sassafras River location.

The 11-room brick inn is named for Catherine “Kitty” Knight, who reportedly saved two homes from burning during the War of 1812. 

On May 3, 1813, she pleaded with the British to spare the property she rented and an older woman’s home. In 1836, she bought the circa 1755 house and lived there until her death.

In a 1932 article in Every Evening, the precursor to The News Journal, the Eastern Shore icon is referred to as “historic.” 

Hometown Hero

Jester said he was conceived in the inn when his parents decided to stay overnight after a Halloween party rather than drive home. The budding chef grew up about five minutes away from Kitty Knight House.

Jester’s father, Bob, also owned a Newark sports bar and Harbour House Restaurant in Chestertown, which he sold after learning he had stage 4 lung cancer. 

On his first appearance on “Guy’s Grocery Games,” Jester told Guy Fieri about his dad’s battle. The chef/host graciously asked Jester about his father’s health when Jester returned for a second, successful run at the prize. Bob Jester died in 2016.

After winning the “Pressure Cooker” series, Jester was the featured chef at a meal at the new Deep Blue Kitty Knight, and Bouchard got an idea.

“He has always loved the area, and in the back of my mind, I knew if there were an opportunity to work with him, I would reach out,” Bouchard said.

Jamestown’s executive chef, Patrick Bradley, had his hands full with Jametown’s north Delaware eateries and busy catering division. 

Jester knew Kitty Knight, Galena and how to run a kitchen. 

They agreed to collaborate.

Kitty’s new dishes

Since joining the team, Jester has focused on service with a smile and the menu, which he’ll unveil on Tuesday, May 14. 

The chef has built a foundation on Eastern Shore cuisine; he made crab cakes on the first episode of “Pressure Cooker.” So, he knows his audience’s tastes.

New dishes will include Jester’s popular smoked foods, including scallops, barbecue pork and slow-and-low ribs. There will be local Angus beef and selections from area wineries. 

He’ll also feature Harbour House’s broiled rockfish with lemon-scented creamed corn.

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Jester said many Deep Blue diners fondly remember his dad. One table of four sang the praises of Bob Jester’s crispy spinach, so Jester went to the kitchen and made it for them.

Like father, like son.

Deep Blue at Kitty Knight will hold several special events to introduce Jester to the neighborhood.

On Thursday, May 23, 6-8 p.m., the public is invited to a happy hour featuring DJ Andrew Hugh.

Deep Blue will feature a performance by Love Seed Mama Jump on Friday, June 28, at 7 p.m. and continue the music during the summer season.

For a schedule visit

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