Trump Tower Chicago Tailspins – Can’t Find Tenants


There are numerous stories about the many failures of Trump and his plethora of business dealings and other business endeavors. In a recent investigation into a Chicago-based Trump Tower, The Real Deal analyzed the how’s and why’s behind the business move and discovered that the Trumps have had numerous deals that have fallen flat on its face in the city.

The Trump Tower in question here is one that is situated in a competitive retail market within Chicago. All around this location any comparable space hasn’t languished as long, where here, the Trumps have gone through countless leasing agents, ending in disaster. The marketing materials for this location even removed the Trump name from it’s materials, only to reinstate the name again.

One of the biggest issues with this project could have been it’s 2009 asking rent price of between $100-$150 per square foot. Per a developer’s estimates in 2018, the space’s value sat at about $23.33 per square foot. Talk about a decrease in value.

Even with the presence of Don Trump Jr. last summer, his efforts to kickstart leasing activity fell flat – Out of 77 potential tenants, all said no to this Trump Tower’s brokers.

‘About a year before the 2005 groundbreaking for Trump International Hotel & Tower, Trump Organization executive Charles Reiss met the late Chicago real estate broker Bruce Kaplan and his colleague, Leslie Karr. The Trump family, Reiss said, wanted advice on how to market the retail space that would face the Chicago River at the tower’s base.’

Check out this video of Trump Tower Chicago and all that it could have been… but isn’t.

In an unending charade of various characters and hands, one of the first leasing brokers on the project had a sort of fantasy about what this Trump Tower location could be, inviting high-end merchants to join “one of the most trafficked shopping destinations in the country.” The statement was risky as the pitch led the broker down a tunnel that resulted in no deal.

‘We listened to all their bullshit about how great it was going to be…They were trying to pawn it off like it was part of Michigan Avenue.

‘We were like, no, it’s not.’

Per The Real Deal’s investigation, the area in question seems to be a sort of dead-zone, with other nearby retail spaces sitting vacant, including the Wrigley Building plaza and two other locations off North Rush Street and East Benton Place in the Lakeshore East area in Chicago.

Furthermore, the location of all of these businesses are one that brokers and shoppers cannot ignore; they are all notoriously hard to access. In addition, and for Trump specifically, his building’s esthetic was not popular. So unpopular, the Mayor chimed in about her distaste.

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After all of this time in business, the Trump Tower Chicago location is hanging by a thread with only one small retail tenant in operation.

Trump Tower locations have had a great deal of controversy over the years, and now thanks to this reporting, we have a better understanding of how something so grand, in the end, was never grand to begin with.

Featured image via YouTube screenshot.