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The Last Holdouts

The forces of development and change are strong in Chicago, but so are the stubborn (or steadfast) folks who are determined to stay put.

Published Sept. 6, 2017

The last remaining Jazz Age landmarks on the South Side. The tiny 19th-century rowhome sandwiched between highrise condos in River North. The only manually operated elevator in a public building. In Chicago, a land of broad shoulders and ornery tempers, we root for people fighting the impossible fight—those who stare into the face of enormous change and say, Nope. In “The Last Holdouts,” we look at the people, places, and things that are sticking around while everything around them transforms.

Have an idea for a story in this series? Email us.

Chicago’s Last Manual Elevator

Automation be damned. There’s something beautiful about seeing the inner workings of a people mover.

The City’s Oldest Restaurant Is Moving—But Not Far

In 1892, Daley’s opened because of a construction boom. Now a new one is displacing the city’s oldest restaurant—and giving it a new opportunity to thrive.

A Story of Squatters’ Rights, a House from the World’s Fair, and a Remarkably Stubborn Man

Ellis Bennett, who made a living as a duck hunting guide on Wolf Lake, lived illegally in the Delaware House for almost 30 years.

We “Ran the Circuit” at Italian Village for Its 90th Anniversary

How much history (and fine wine) can you imbibe in three hours at Italian Village? We spent equal time at the Village, La Cantina, and Vivere to find out.

The Last Memorial Left to Shirley Ellen Lee, Who Was Loved Very Much

More than 50 years ago, a nine-year-old girl died in a fire, leaving her widower father alone and distraught. He spent the next weeks of his life placing memorials for her across the city—and today, only one remains.

Monk’s Pub, Quirkiest Bar in the Loop, Isn’t Going Anywhere

Sorry, condo developers. Mike Shaker isn’t looking to sell this 48-year-old watering hole that connects Chicagoans to farflung places and a bygone era.

It’s Not Taboo to Be Sexy, or Stay Small, in Lake View

I run a successful sex shop with my parents. Here’s what I’ve learned about the retail industry.

Will This Meatpacker Pack Up and Leave Fulton Market?

Dozens of food distribution businesses have left Fulton Market as glitzy restaurants and boutique hotels move in. Bridgford Foods is staying—for now.

The Last Printer on Printers Row

Chicago was once the publishing capital of the country. If it wasn’t for a single beer in 1982, there wouldn’t be any namesake businesses in this South Loop district anymore.

An Island in Wrigleyville

Wrigleyville in the age of the Ricketts is a sea of development. Jose Luis Resendiz, and the shop his family’s owned for 51 years, is just trying to stay above water.

The South Side’s Last Remaining Jazz Landmarks

Once a bastion of jazz greats, many grand venues in and around Bronzeville have shuttered. These buildings hold on to some of that history.

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