Peggy Delores Bailey, a beloved waitress who could serve 40 people without using a pencil, died of heart failure and respiratory issues May 12 at Dublin Methodist Hospital in Dublin, Ohio. The former Catonsville resident was 82.

Greeting her patrons with “Hey, sugar,” or “Hey, honey,” or “Hey, baby,” she was known as the mayor, queen or legend at Catonsville’s Jennings Cafe, where she worked until being sidelined by a fall in early 2023. She worked at Baltimore restaurants for 63 years.

“A little lady dressed in a faux tuxedo of black and white comes shuffling through the noisy crowd in her Easy Spirit shoes like some kind of Super Mario, hefting a tray of stewed tomatoes and fried oyster sandwiches in one hand and a draft beer in the other,” is how she was described in a 2004 profile in The Baltimore Sun. “The white hair, the pudgy cheeks, the nod and a wink – might as well be Mrs. Claus.”

“When she wasn’t at work, she talked about work,” said her son, James R. Bailey.

Born Peggy Delores Jones in Roanoke Rapids, North Carolina, she was the daughter of William Jones and his wife, Virginia. As a teenager, she worked in tobacco barns, picked cotton and did a night shift at a textile mill. She hated the work and was determined to be a waitress.

She got a job as a carhop on roller skates at the Puppy Palace in Roanoke Rapids, she told The Sun in 2004. She recalled the place sold hot dogs and cheeseburgers and “no booze.” She made $30 a week in 1957 and after graduating from high school, she, with her sister in tow, moved to Baltimore and joined her mother, who was already living here.

She landed a job at a Park Heights Avenue delicatessen, Duke & Lou’s, a place she called “Dukey-Loos.”

“She told (owner) Duke Bergerson she didn’t know anything about Jews, pastrami, corned beef, lox or bagels,” The Sun’s 2004 story said. “‘I was raised on beans and collard greens,’ she said. He said, “‘Don’t worry, just write down the order and bring it to me.’”

“Her first day of work, she was nervous. She had eight Jewish customers, one of them, (was) a handsome young man. He ordered a tongue sandwich,” the story said. “Peggy cussed him up one side and down the other.”

The restaurant’s owner apologized to the customer and accompanied her to the kitchen to show her the cow’s tongue.

She moved on to work at a Holiday Inn near the Pimlico Race Course. One Preakness Saturday, she went to work and discovered she was the only waitress on the floor.

“The place was overrun with people, and the girl at the cash register whispered that Adolph and Joel Krisch, the country’s largest Holiday Inn franchisees, were in the crowd waiting for breakfast. ‘Thanks for telling me, Wanda,’ Peggy told the cashier.

“Before you knew it, Peggy cornered the two millionaires, handed them coffee pots. ‘They’re your customers, too,’” she said.

Before landing at Jennings Cafe in Catonsville in 1981, she worked at the Candlelight Lodge, also in Catonsville. Her first flambe almost set the place on fire. She used to wear a basket weave wig that would get snagged in the wagon wheel lamp at the Middleborough Inn in Eastern Baltimore County.

She married James Bailey, a worker at the Sealy Mattress factory in 1961. After he became paralyzed during a heart procedure and later died, she began working double shifts to support two sons. She and the boys lived with her mother for years, and when her mother died in 2002, she rented an apartment near Jennings Cafe.

While at the popular Frederick Road cafe, she often steered customers away from certain main dishes or specials that she didn’t think were worthy. She also raised an eyebrow if they ordered, in her opinion, the wrong item.

She got to know her customers’ preferences, such as a woman who gave up whipped cream during Lent, but not the accompanying pie.

She would say, “This is not Tio Pepe’s. This is not the Prime Rib. It’s just what it is. It’s just plain food.”

Steven Iampieri, who owns the cafe, said, “I did not realize what an impact she had until I bought Jennings in 2017. I was so fortunate. She could have been a deal breaker.”

A couple of times a year, she dined at the Prime Rib with friends. She ordered roast beef and cream of crab soup.

Her culinary specialty was stewed tomatoes.

“She was also famous for her fried chicken and playing a card game called pitch,” her son said. “She enjoyed herself at racetracks, a casino and watching Orioles games. She didn’t have a gambling problem. She just liked the excitement.”

A life celebration will be held from 1 p.m. to 4 p.m. June 21 at Jennings Cafe in Catonsville.

Survivors include her son, James R. Bailey, of Powell, Ohio; a sister, Patricia Shipley, of Baltimore; two grandsons; and a great-granddaughter. A son, Christopher Bailey, died in 2023. Her husband, James Bailey, died in 1978.

Have a news tip? Contact Jacques Kelly at jacques.kelly@baltsun.com and 410-332-6570.