RIVER NORTH — President Donald Trump is back in the Oval Office, and the Chicago Riverwalk is thriving.
In this renewed landscape, a global team of real estate brokers is seizing the opportunity to lease the long-vacant retail space at Trump International Hotel and Tower, which has been empty since it opened in 2009.
The Trump Organization has engaged Newmark real estate brokers from Chicago, New York City, and London to search for tenants capable of investing in the space and willing to operate beneath the towering 20-foot-tall “Trump” sign in a city where the president has often expressed disdain.
Located at 401 N. Wabash Ave., the double-decker retail area at the base of Trump Tower has been idle for 16 years, save for a hair salon near the hotel lobby and a tour boat company operating out of the plaza. This space, spanning 70,000 square feet, holds the dubious distinction of being the longest-running retail vacancy in Downtown Chicago for spaces over 5,000 square feet.
James Schutter, a Newmark broker based in Chicago, commented on the situation, noting that there has been “great initial interest” in the retail space since Newmark took on this leasing endeavor in May. This marks the fourth attempt by different broker groups to fill the vacancies.
“The waterfront visibility, Michigan Avenue, the river, it’s almost ground zero for Chicago. People take selfies with Trump Tower behind,” Schutter remarked. “To me, it’s a business opportunity we’re presenting. The Trump name can have both negative and positive connotations. We will find individuals who view the Trump name positively.”
However, skepticism remains among some retail brokers and developers about whether enough has changed to fill the long-empty retail space. Factors such as low ceiling heights, political controversy, and a location that is not readily accessible have contributed to Trump Tower’s storefronts remaining vacant in an area that is otherwise fully leased, particularly near the popular Riverwalk and upscale restaurants.
Despite a notable six-point increase in the support for Trump during the 2024 vote in Chicago, where Kamala Harris still garnered 77 percent, protests continue to attract attention at the plaza outside the tower.
“It’s a very challenging location,” broker David Stone noted. “That sign becomes your sign.”
Newmark has produced marketing materials titled “Where Luxury Meets Legacy, Never Settle,” which envision creating two 10,000-square-foot restaurants on the terrace level of Trump Tower and two larger entertainment features on the river-adjacent level, one of which could be a golf simulator. The terrace may also accommodate four smaller retail operations and a river-facing “Trump Store,” a name that was renamed to “Specialty Store” shortly after inquiries were made about it.
Schutter, who refrained from commenting on specific deals currently in play, indicated that his team is actively showing the space to “unique users.” He mentioned the possibility of a café tenant moving in as early as next summer and stated that “For Lease” signs will be posted soon.
“We believe this is one of the highest-profile locations in the urban Chicago environment at present,” Schutter asserted. “Access is much better than it has been promoted in the past.”
The leasing price for the retail space is noted as “negotiable.”
As new landmark leases surface, such as a Harry Potter-themed store, the overall trend in the Downtown retail market suggests a slow recovery from the pandemic’s impact on foot traffic and changes in commuting habits. For instance, the Riverfront steakhouse Chicago Cut has recently expanded.
However, several challenges continue to face Trump Tower. Notably, the retail space’s orientation toward the river complicates access from Wabash or Michigan avenues, and this location does not enjoy the same foot traffic seen along the nearby Riverwalk.
Broker Gregory Kirsch characterized the space as akin to the Statue of Liberty — visibly prominent but difficult to reach.
“To maximize its potential value, the property needs to open up from North Michigan Avenue,” developer Mark Goodman stated.
Conversely, David Goldberg, CEO of Goldstreet Partners, remains optimistic about the future of Trump Tower’s retail space, claiming there is excitement surrounding the opportunity to secure “the most talked-about lease in the country.” He has actively promoted the space through social media, garnering interest despite facing numerous negative comments.
“There’s interest and excitement,” Goldberg shared during a phone call from Ibiza. “The river has just gotten better. Right now is an excellent time.”
Schutter confirmed that Goldberg is representing “a number of tenants” in serious discussions to lease the property, including a noteworthy café targeting a broad audience, although neither party provided further details.
A large-scale restaurant in that desirable stretch of the Riverwalk could typically command annual rents between $800,000 to $1 million, with a sales target of $15 to $20 million needed for profitability, according to Kirsch.
“Everything leases at the right price,” Kirsch commented, emphasizing that distinctiveness and social media presence can bolster off-the-beaten-path restaurants.
The Trump Organization has not commented on inquiries regarding this matter.
During the tower’s construction in 2008, Trump projected that he would attract “very fine” dining establishments and notable retail partners. However, by 2012, he ceased pursuing tenants for the space, later suggesting in 2014 that the area might be repurposed as conference rooms for hotel guests. By 2018, brokers were revisiting efforts to lease, drawing up materials that avoided using the Trump name.
Trump has been quoted on multiple occasions claiming that the development is “worthless” as a tax deduction while still profiting from brand-related income and his famous television show, “The Apprentice.” The 92-story tower has notably struggled with occupancy rates, leading many residential units and hotel rooms to be sold off to outside investors, as reported by Crain’s Chicago.
As of last estimates, the retail portion of the Trump Tower was assessed at approximately $20 million, an evaluation that could dramatically increase if The Trump Organization successfully secures reputable tenants, Kirsch noted. Meanwhile, Trump continues to claim tax breaks, including a $1 million tax refund on the vacant space, a contentious issue given the mixed history of the building.
“There is some value in writing off a non-performing asset,” Kirsch added, “but substantially more value in having restaurants generating rent.”
Trump’s business image benefits from having his name prominently displayed over Chicago’s Downtown, a factor whose financial implications remain uncertain. His reelection has seemingly led to increased sales of branded merchandise and cryptocurrency dealings even as his properties struggle financially, according to investigations by The New York Times.
On a summer weekday afternoon, a modest crowd of tourists gathered outside the empty retail space at Trump Tower. Their opinions varied from lukewarm acceptance to firm rejection when discussing whether they would patronize a business within.
Many expressed uncertainty about separating the man from the building, with most declining to provide their names for the story.
“If you’re doing business in the building, you’re supporting the guy, or he’s supporting you,” commented Nick Buckley from Colorado. “Probably not for me. I’m definitely not a Trump supporter.”
“If it were a local business owner in there, I’d support them,” said David Zena from Kansas City. “Doesn’t mean I’m supporting his policies.”
“I’m a Republican. It doesn’t matter to me,” remarked Dustin Grigsby.
A dock worker mentioned observing pedestrian traffic near the locked retail area “maybe once.” A glance through the dark glass revealed unfinished interior spaces cluttered with construction materials and equipment, as a private security guard patrolled the vicinity.
Across the water, O’Brien’s Riverwalk Café buzzed with patrons, highlighting the competition.
“I always thought a hot dog stand would be a great idea,” suggested Mike Borgstrom, President of Wendella Tours & Cruises, whose business utilizes the docks located outside Trump Tower. “But I’m not sure if that’s the kind of establishment they’re looking for.”
Newmark has previously assisted The Trump Organization in selling its Washington D.C. hotel after another broker withdrew their involvement post the January 6 Capitol riot. The firm also successfully leased an office this year in New York City’s Trump Tower.
Schutter and his local partner, Larry Kling, previously secured tenants like Ghirardelli, Walgreens, and Peet’s Coffee for the Wrigley Building plaza, which itself had an extended vacancy period.
The Trump Tower’s retail space features “wide-open floor plans,” with Newmark open to making adjustments to meet tenant needs, Schutter indicated.
“We are deeply engaged with potential tenants regarding design and what will create the strongest space,” Schutter said. “We aim to present a compelling opportunity to the right operators.”
Tourists like Buckley noted that the imposing “Trump” sign was one of the first things they noticed during their sightseeing trips around Chicago. The looming question remains: will this notoriety ultimately contribute to revitalizing the struggling retail space?
image source from：blockclubchicago
