When Steve Iampieri was looking to buy Jennings Cafe in Catonsville in 2017, he had to know: Did Miss Peggy come with the deal?

Peggy Bailey, who had been serving at Jennings since 1979, was synonymous with the eatery. In her mid-70s at the time, she’d amassed such a loyal following at the restaurant that she even had her own section, Peggy’s Parlor. Guests would wait to eat if it meant she could be their waitress.

She never wrote an order down, but her memory was nearly flawless. She just looked at people’s faces and remembered their requests. On the occasions she did mess up, customers took what she gave them happily. She had that effect on people.

About 200 people turned out to celebrate her career when she retired in 2023, forced to the sidelines after an injury. It’s almost a sure bet that just that many, if not more, will come back for a celebration of life on June 21.

Bailey, who was also a hardworking mother and dedicated Baltimore sports fan, died May 12 after experiencing heart and breathing issues. She was 82.

“She never forgot a person’s name, what they did, never forgot what they drank,” Iampieri said. “She was the consummate hospitality professional.”

She was born July 5, 1942, in Raeford, North Carolina, to Virginia and Bill Jones. Life wasn’t always kind in her youth: Her parents were young when they had her, and her father was an alcoholic. At age 9, she started working in tobacco barns. When she was 12, her parents welcomed another daughter, Patricia, whom she loved, but the age gap made it difficult to connect.

As a young teenager, she started dating Jimmy Bailey, the brother of her best friend. And she started her career in the service industry, working as a carhop — on roller skates — at a drive-in restaurant. Later in life, Peggy joked that she’d been waitressing so long that she split the tips at the Last Supper.

At home, her mother decided to leave her father, and she moved to Baltimore. Peggy turned down a college scholarship to follow her mother after graduating from high school, and Jimmy came with her. They married and had two sons, Roland and Christopher.

Peggy Bailey continued working in food service, first picking up shifts at a kosher deli and later taking jobs at various inns across the metro area.

Her marriage had a rocky start, and she picked up some bad partying habits from her husband, Roland Bailey said. They split up a few times and got back together, but they loved each other and eventually settled down.

Their relationship came to a tragic end in 1978 when Jimmy Bailey died unexpectedly during heart surgery. Their oldest son was just 16.

“He left my mom, in her mid-30s, two children to raise, pretty much on her own,” Roland Bailey said. “So I said, ‘Mom, what did you do?’ She said, ‘I don’t have time to complain. I just had to go to work and take care of you boys.’”

Peggy Bailey started working lunches at Jennings Cafe on top of her dinner shifts at the Middleborough Inn in Essex. She lived nearby and loved Jennings, a place she’d frequented before working there. The Catonsville restaurant quickly became her job of choice.

“She started working full time and doubles,” said Omar Jennings, who previously owned the cafe. “And everybody loved Peggy. She would kid around. She was more of a friend waiting on the customers than an actual waitress.”

She held two jobs for more than a decade. In 1989, she left the inn. After that, it was all Jennings all the time.

Bailey built an army of regulars, charming them with her North Carolina accent and perfect memory. If they asked for her thoughts on a dish, she was always honest.

“My word is gospel. I will tell you that right now,” she said in a 2023 interview with The Banner. “When I tell you something and you don’t listen, that’s your mistake. Not mine.”

Margaret Bowler, one of Bailey’s many regular customers, said she was drawn to the waitress because “she really did care about people.” She knew intimate details of patrons’ lives, lending a listening ear and often a helping hand. When one customer‘s spouse died, she attended the funeral.

Some people say that if you love your job, you never work a day in your life. Bailey meant it.

“Somebody said to me after she died that he hoped she was in heaven being waited on,” Bowler said. “I said, ‘Actually, her idea of heaven would have been a table of 20 at Jennings where she could chat and remember all the orders.’”

When Cindy Foy started working at Jennings in the ’90s, Bailey trained her, and they became “best friends and partners in crime.” They spent many nights together drinking after work and playing cards. Bailey’s drink of choice was a Miller High Life.

They also attended Orioles games, one of Bailey’s favorite pastimes, and went to Preakness together.

After retiring, Bailey moved to Ohio to spend more time with Roland and her grandchildren. Her youngest son, Christopher, had recently died, and she relished the opportunity to be with her family. She and Roland bonded over a love of country music, and she dropped everything to help the grandkids when they needed it.

Her son is not surprised by the outpouring of support for his mother. He was among the hundreds who experienced her love and dedication.

“People loved her,” Roland Bailey said. “She had taken care of people and their children, their children’s children — generations of people my mother waited on. She waited tables until she was 80 years old. Who does that?”

Banner reporter Julie Scharper contributed to this article.

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