Democrats Taunt Trump At Trump Tower Chicago Ahead of Convention

Amid reports that Donald Trump’s campaign will hold daily briefings at the Trump International Hotel and Tower in Chicago during the Democratic National Convention — a cute lil’ transfer of campaign funds to the candidate’s personal business portfolio — Democratic operatives are having some fun trolling their rival ahead of the convention’s kick-off on Monday.

Party operatives, armed with a high-powered projector, booked themselves a room across the street from Trump Tower to display the message “Trump-Vance: Out For Themselves” — along with other slogans intended to rankle, rile, and otherwise irritate the candidate — across his 92-story building’s gleaming glass facade. 

The slogans “Trump-Vance: ‘Weird as Hell,’” “Harris-Walz: Fighting for You,” and “Project 2025 HQ” are also in rotation. Since taking over the ticket, Vice President Kamala Harris and her running mate, Minnesota Gov. Tim Walz, have frequently described Trump and his VP nominee, Sen. J.D. Vance, as “weird,” thoroughly annoying Trump. As for Project 2025, Trump has furiously (and unsuccessfully) sought to distance himself from the conservative personnel and policy program, intended to help him hit the ground running in a second term, as it’s gained notoriety and generated controversy.  

The Skidmore, Owings & Merrill-designed building — one of Trump’s last big construction projects before he became president — is also one of the biggest failures to hit the Chicago River since the infamous Dave Matthews Band tour bus incident. 

In May, The New York Times and ProPublica reported that the former president may owe more than $100 million, plus interest and penalties, to the Internal Revenue Service related to the building, after he wrote off its astronomical losses twice. According to the outlets, Trump declared a $651 million loss on the project in 2008, and $168 million in further losses over the following decade.

Trump has a well-documented habit of using his own properties for campaign events, enriching himself with his supporters’ donations. A USA Today report in April found that Trump’s joint fundraising committee had already spent at least $411,287 at Trump’s Mar-a-Lago club in Palm Beach, Florida, and an additional $62,337 at Trump National Doral Miami. Federal regulations allow campaign expenditures at a candidate’s business if the campaign pays “fair market value” for them. (The cheapest room at the hotel located inside Trump Tower Chicago is going for $666 with the Democratic convention in town this week, according to its website — close to double the usual rate.)

“Donald Trump is just a major grifter,” Abhi Rahman, deputy communications director for the Democratic National Committee, says about the Trump campaign’s plans to use the candidate’s building this week. “He’s always been out for himself, and this is just another example of this.”

In a separate statement about the DNC’s guerilla art project, Rahman wrote: “Tonight, everyone is seeing a preview of the contrast that will take center stage this week throughout the Democratic National Convention. Vice President Kamala Harris and Governor Tim Walz have proven records of delivering for working families, and now, they’re running to lead our country into a brighter future.”