Part 2 of Joe Smazal’s conversation with Leon Walker, Founder & CEO of DL3 Realty, goes deal by deal.

When Target closed both of its South Side stores, the city refused to let it sell to the usual disposition list.

One alderman knew somebody.

That call became the Blue Cross Blue Shield center in Morgan Park, 500 jobs, ribbon cut in masks six feet apart, and then the Discover (now Capital One) center that doubled it to 1,000.

Leon explains the design trick he borrowed from a failed senior housing deal to make a dark big box work as office space, and why “venture tenants” are the ones willing to see it before it exists.

We also get into why the hardest part of building a grocery store is building a grocery store – vertical integration, long-term supply contracts, Chicago’s produce terminal advantage, and what it actually took to walk Jewel executives through Woodlawn in person.

Plus the 25-acre West Pullman industrial assembly on the former Plano Manufacturing site, and two downtown projects: ACODA at Pritzker Park and the 135 S. LaSalle conversion of the Field Building, on the ground where the first skyscraper stood.

Leon closes with the Five T’s he gives emerging talent: talent, timing, team, treasure, and truth.

And why the last one is the only thing that carries you through a deal that might not work.

Chapters

00:00 Revitalization vs. gentrification

01:59 Pre-COVID, the “retail apocalypse,” and reading durable trends

04:35 Target leaves the South Side, and the city blocks the sale

07:40 Solving the dark big box: courtyards and light wells

11:30 Discover doubles the model to 1,000 jobs

12:20 Why nobody built a grocery store for 50 years

16:38 Selling Jewel on Woodlawn in person

18:41 Whole Foods, Englewood Square, and the 10 tenants that followed

19:53 West Pullman: 25 acres and 400,000 sq ft of industrial 24:30 Downtown, ACODA and 135 S. LaSalle

28:04 What makes an office-to-residential conversion actually work

33:02 The Five T’s

38:48 Why he loves Chicago

42:48 Getting the city back over 3 million