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Daley's Restaurant Waitress Recalls Three Decades of Serving Breakfast in Woodlawn

Welcome to a Breakfast Week edition of Lifers a feature in which Eater interviews the men and women who have worked in the restaurant and bar industry for the better part of their lives. Up now, Rose Gillespie, a waitress for 34 years at Daley's Restaurant.

Rose Gillespie
Rose Gillespie
Nagle Photography

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Rose Gillespie has seen Woodlawn's highs and lows. For 34 years, the waitress has served morning customers at venerable Daley's Restaurant, one of the city's oldest restaurants. The throwback eatery has been in the South Side community since 1892, serving breakfast, homemade soul food, pies and biscuits.

Daley's roots stretch back to the Columbian Exposition and has gone through two buildings at the same site. The restaurant's evolved — when Gillespie started she would just yell customers' orders to the cooks; they didn't write them down on paper. Proudly wearing her apron, both she and co-owner Mike Zar chatted about Gillespie's career in this South Side community.

Why did you enter the service industry?

I worked in keypunch for 13 years but I still worked as a waitress, part time. In '82 I got laid off from two different insurance companies, and I didn't make the amount of money that I wanted. Then I said 'I know where I can make my money.' And I went back to waitressing full time.

Do you treat regulars differently?

No. I treat them all the same way. [Shaking her head] They're all the same to me.

How do you ensure customers come back?

Good soup. Good coffee.

MZ: Rose has her own clients, they come into see her. They come into her section. Sundays, she gets families that come in; they only want to sit with Rose. It's hard to see new customers, because she gets so many that she's been around for so long. But like she said, she treats everyone fair. She really does.

Daley’s Rose Gillespie Eater Chicago/Nagle Photography

What's the best part of the job?

I'm a people person, I like being around people. In the years that I've worked I've had a lot of good people coming in.

After working with other waitresses through the years, do you see yourself as a mentor?

MZ: Everyone respects Rose...they also know to stay out of her way when she's working. Don't mess with Rose.

What does Daley's mean to Woodlawn?

I think it's a family place. Because a lot of people have gone, moved out, whatever and came back. This is where they can come in as a family no matter what.

Rose Daley Restaurant food

Do you ever get grouchy on the job?

I don't think so, you know sometimes things happen anyway, it doesn't matter what I would have done. One day a client may touch you and it wasn't right, but then you brush yourself off, you got to get back to work.

Mike, what makes Rose different?

MZ: She has more class than anyone in this restaurant. The way she carries herself, the way she speaks, the way she treats people; it's the whole thing.

So you listen to R&B in the car on the way to work. Who do you listen to in particular?

Luther [Vandross].

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