“Vanity drove Trump to break the bank, as usual,” says Elliott, who will retain a small piece of the Chicago operation. “I understand the urge; after all, I launched Time Out New York mostly so I could have a magazine that goes by TONY for short. But what can you do with Time Out Chicago, really? TOC stands for ‘table of contents.’ He’s welcome to it.”

Elliott briefly considered merging TOC with the Tribune Co.’s RedEye, but soon realized EyeOut Chicago might struggle for consumer acceptance. “After all, it’s only fun until someone puts out an eye,” he notes.

Trump held a meeting with Time Out Chicago staff Tuesday outside his new downtown hotel.

“You’re all fired,” he said to the assembled group, which broke out in nervous laughter after he flashed an odd smile that one attendee characterized as a “cross between a grin and a grimace. It was a grinace.”

“I am hugely excited about what is a truly huge opportunity for Trump Entertainment and an even huger opportunity for the people of Chicago,” Trump announced.

He went on to outline how he will leverage to enhance the stature of his real-estate and entertainment empire. “The keys are synergy and product placement,” the mogul said.

Cross-brand promotions will include making recently hired Editor-in-Chief Frank Sennett compete for his job with Omarosa Manigault Stallworth and a series of what Trump referred to as “T-list celebrities—which, if you ask me, is better than A-list” during the next season of The Apprentice on NBC.

As other openings in editorial and operations occur, they will be filled by finalists of the Miss Universe, Miss USA and Miss Teen USA pageants, which Trump owns in partnership with NBC Universal. Former Miss USA Tara Conner, who completed a highly publicized stint in rehab last year, will take on the newly created post of Time Out Chicago brand ambassador.

“I’m a huge believer in second chances, and Tara embodies the class and spirit that will drive Time Out Chicago to new editorial heights,” Trump said. (You can read an excerpt of Conner’s new nightlife column here.) Upcoming cover subjects will include Trump’s Atlantic City casino and The Apprentice cast.

“However, my journalism adviser, Medill dean John Lavine, told me it would be inappropriate to market Trump properties on every cover,” Trump added. “So some future cover slots will be open to the highest bidders from outside the organization. As I understand it, that constitutes a win-win in terms of revenue and high ethical standards.”

Trump deemed Time Out Chicago “the only blue-chip publication worth acquiring in this city.”

“The Chicago Sun-Times is obviously a distressed property, which can be a very appealing investment, but I’d already torn down their headquarters to make way for this hotel, so I thought it was best to move on,” Trump said. “I also considered buying the Chicago Reader, but ultimately I wasn’t interested in any property also sought by a company with a ridiculous name like Creative Loafing.” He went on to call CL “Atlanta’s best export since Michael Vick…. Seriously, they are nonhuge.”

An initial overture to buy Tribune Co. from real-estate titan Sam Zell went nowhere after Trump discovered the company has discontinued the practice of breaking off chunks of landmark buildings from around the world for installation on the walls of Tribune Tower.

“I have to tell you, I wish I’d thought of that for Trump Tower in Manhattan,” Trump said. He admitted he’s now trying to figure out what to do with the hunks of the Temple Mount, the Louvre Museum and Disneyland’s Space Mountain that he chiseled off during recent business trips.

For a sneak preview of the new Time Out Chicago, read on.

Is this some kind of joke? Yes, actually. The above was part of TOC's 2008 April Fool's issue. Read more about it here.

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