A look back at Diamond Lil’s restaurant in Belleville and the memorable woman behind it

A BND series about what makes Belleville and southwestern Illinois a unique place to live. Send questions and tips to newsroom@bnd.com.

Over the last few years I’ve gotten used to writing about restaurants. What’s coming to the area, openings, closings, the stuff in between.

But I don’t usually get to write about those that once were.

You know what I mean – the places that are long gone, where memories were made and are still remembered today.

Diamond Lil’s in Belleville is one of these places. And the woman behind it, Lillian “Diamond Lil” Krupp, was even more memorable.

Krupp was known for her colorful appearance, which included her bright red bouffant hairstyle.

She wore earrings “as big as 10-cent gumballs to a color-coordinated necklace,” according to a September 1984 News-Democrat article. Her look included the orchid in her hair, bright lipstick and matching nail polish and the rings on her fingers.

Her trademark appearance became a symbol of her restaurant. A caricature of her likeness became part of her restaurant’s branding and was found on the signage, the menus and even the napkins.

Some members of the I grew up in Belleville, IL Facebook group still remember Krupp and Diamond Lil’s.

“I was a bus boy for her in the ‘70s!! Lived right around the corner on High Street so [I] walked to work most evenings after school.” – James Hopper

“Lil was a classy lady.” – Mark Scott

“We had Thanksgiving dinner at Diamond Lil’s when I was about 12. She was there and I remember my dad joking around with her. I don’t remember why we ate out that year, my mom always cooked Thanksgiving. It was always a treat to eat out and that place seemed fancy to me.” – Donna Gutierrez

“Always had good food. Lillian Krupp was a very nice lady. We would go eat there on special occasions, birthdays, anniversaries and parties.” – Bobbie Benesh

“I tended bar for Lil. She was a fascinating woman.” – Brenda Holcomb Santel

“I remember those days! I was super little and my grandma was very good friends with Diamond Lil. She was absolutely beautiful, red hair and her jewelry was amazing. She sparkled. We had lunch and dinner at least once a week. I had my own set of silverware to eat at her restaurant.” – Lisa Burns-Wojick

“I remember Lil. She was quite a character. One of my first dates in high school was going to Diamond Lil’s. My parents used to go there [with] some … good friends as well. Always a good experience.” – Deb Reinhardt-Baldwin

“We gave our mom and dad a surprise 25th anniversary party at Diamond Lil’s. She helped make it so special. Great Lady!” – Rita Wright

“I remember her. I used to work the late shift at Hy-Ho Restaurant, and her and her bartender – I believe his name was Bob – used to come in after her place closed for the night. Sweet lady.” – Sheila Meyer

BND 071582 Diamond Lil's Look by Jennifer Green on Scribd

My own memories of Diamond Lil’s are very limited and very vague.

I think the only reason I have any memory of it is because my uncle, Tom Green, played music there regularly and knew Krupp pretty well.

I remember a Diamond Lil doll that my cousin, Angie, had when we were kids. She might still have it.

Tom has photos, newspaper clippings and a few other keepsakes from those days. And stories. He always has good stories to tell.

For now, here’s the story of Lillian Krupp and Diamond Lil’s, pieced together from articles in the BND’s archives.

An early start in the business

Krupp got her start in the restaurant business when she was 12 years old, helping her parents, Edward and Eva Krupp, at their New Athens restaurant, Krupp’s Café.

At 21, Lillian Krupp got her license to run a restaurant. She eventually took over the family business.

During her time in New Athens, she became a member of the Licensed Beverage Insurance Board and served on the board of directors of the Licensed Beverage Association.

She was a member of the St. Clair County Tavern Owners Association. A February 1955 news item referred to her as president of the organization. She was re-elected in November 1955.

Krupp later served as the association’s secretary for six years before she was elected as president again in 1966. By the end of her term in November 1967, Krupp had retired as a tavern owner but maintained her association membership.

See also served as secretary of the New Athens Chamber of Commerce from 1958 to 1965.

Coming to Belleville

Krupp’s restaurant career in Belleville started in 1968 when she became the manager of Town House Restaurant at 400 S. Illinois St.

“Business was slow when I came to Belleville in 1968 and took over this restaurant,” Krupp told the News-Democrat in November 1980.

“It was difficult to get this place going, and for a while, I wondered whether business would work,” she said.

Business started picking up during her second year as manager.

For 10 years, she served as the restaurant’s manager, and every year Town House hosted a party to celebrate the anniversary of her tenure there.

On July 3, 1978, little more than a month after Town House celebrated Krupp’s 10th anniversary as manager, the restaurant and adjoining hotel were sold.

She was told she had to leave.

“I was heartbroken when the [Town House] restaurant was sold [in 1978] and I was told I would have to leave,” Krupp told the News-Democrat. “I didn’t know where else I would go. I left some of myself here when it closed.”

Krupp ended her time at Town House Restaurant and Lounge with an ad that read, “A thank you note. Thank you to all my friends and patrons. I’ve enjoyed serving you these past 10 years.”

The message was signed, “Lillian Krupp, Former Mgr.-Town House Rest.”

It was time for Diamond Lil to move on.

A place of her own

Krupp started again in October 1978 when she opened her restaurant, Diamond Lil’s, at 318 E. Washington St. in Belleville.

This address housed multiple restaurants before it became Diamond Lil’s. The building previously housed the Carriage House, Belleville House, Gaslight Manor and Old Downtown Belleville Spaghetti and Pizza Company restaurants.

Since Diamond Lil’s, it housed other restaurants. Today it’s the site of Papa Vito’s Pizza.

From the 1950s until Diamond Lil’s moved in, none of the previous restaurants lasted more than five years, according to a January 1979 News-Democrat story.

Krupp felt that her place would be different and survive because of the unique décor, good food and varied menu.

She said in the 1979 article that she chose furnishings to correspond with the era during which the building was constructed. It was built in 1852. Décor consisted of antiques from the turn of the 20th century or earlier.

But the quality of the food, the furnishings and the energy of Diamond Lil’s didn’t come close to that five-year restaurant mark.

In April 1980, the building was sold to The Pasta House Co., and it was time for Diamond Lil to move again.

BND Diamond Lil's Oct 1978-April 1980 by Jennifer Green on Scribd

Back where she started

Krupp returned to 400 S. Illinois St. on Nov. 3, 1980, taking over the former Town House Restaurant and renaming it “Diamond Lil’s.”

In February 1981, she told the News-Democrat that she was glad her seven-month “vacation” was over, referring to the time between Diamond Lil’s closing the doors at 318 E. Washington and reopening at South Illinois Street.

“But we’re back now and we’re happy,” she said. “And I mean WE because all the people who have been associated with me for a long time, some nearly 12 years, are still with me.”

Diamond Lil’s was a happening place to be, with its menu, regular entertainment and Krupp’s unwavering presence.

She said she had little time for hobbies or social activities outside of the restaurant, and she never went on vacation.

“I should take a vacation, but I worry about my business,” Krupp said in 1982.

“The restaurant business is my life,” she said in 1980. “I’m happier when I’m working. If anybody wants to see me, they know they have to come here to catch me. This is my home.”

BND Diamond Lil's Nov 1980-Oct 1982 by Jennifer Green on Scribd

End of an era

Lillian “Diamond Lil” Krupp died Sept. 2, 1984, at the age of 62.

Diamond Lil’s closed and was sold that October to Betty Underwood, who managed Diamond Lil’s for six years.

The restaurant’s name was changed because “Lil was entitled to that name and it’s up to everyone to make their own name and their own way in life,” Underwood told the News-Democrat.

Diamond Lil’s became Betty’s Golden Slipper and operated at 400 S. Illinois St. until its closing on Sept. 25, 1988.

Multiple other restaurants operated there over the years. Today it’s the site of Mariachi’s Mexican Restaurant.

At the time of Krupp’s passing, others remembered her as both a businesswoman and a contributing member of the community.

“If a place would go down, Diamond Lil would take it over and it would go back up again,” said Tom Wobbe, who worked with Krupp through Belleville Center Inc. He told the News-Democrat that she was influential in downtown business.

“She was very active in civic work. I, and I think Belleville, will miss her very deeply,” said Ken Fischer, who owned Fisher’s Restaurant and knew Krupp for 15 years. “She was a great lady, and she’ll never be forgotten.”

BND 090384 Lillian Krupp Obits by Jennifer Green on Scribd