More doable, Hill suggests, is a 50-story building that would fit in with the heights of surrounding office and residential structures, such as the IBM building and Marina City just to the west along the shore of the Chicago River. But other real estate sources question whether those numbers would work, given Trump's propensity for luxury multifamily product.

"The problem is, can you then match the expectations of size Trump has with that site? Do you want an oversized building there?" Hill wonders.

Daley reminded reporters that if the same logic were applied to the John Hancock building, the city would not have allowed the world's tallest building--at that time--to be built at 875 N. Michigan Ave. in the 1970s.

Although Trump Tower Chicago has become the talk of the town, Whittington cautions the joint venture still needs to hire an architect to draw up specific plans to present to the department of planning and development, as well as hire an attorney charged with obtaining necessary zoning.

Others question whether Trump's name will carry cache in Chicago, where father Fred Trump's style sells better than the Donald's grandiose marketing.

"I think the demographics and absorption rate will be different than New York, but we really see our project as a regional project," says Trump Organization senior vice president of development Charles Reiss. The condominium market, he adds, will be the Midwest as well as international clients.

"His buildings make money for the owners," Reiss says, adding the resale gains in Trump buildings on the East Coast can happen in Chicago. "We believe it can. The proof will be in the pudding."

US Equities assignment included advising Hollinger on potential partners, Whittington adds, and there was plenty of local as well as national interest. "We talked to everybody you can possibly imagine," Whittington says. "Because of the special nature of the site and because of the developments Donald Trump has completed in the past, he provides a unique set of skills."

It also helped that Trump was familiar with Sun-Times publishers Conrad Black and F. David Radler. "There was an instant rapport," Whittington says.

While Hill notes there are infrastructure issues involved with the Wabash Avenue site, Reiss is confident they can be cleared. "We wouldn't be doing it if we didn't think they could be solved," Reiss says. "It's a large site."

However, it does lack immediate Chicago Transit Authority and public transportation access favored by most office developers. By comparison, TrizecHahn's Sears Tower, now the third-tallest building in the world, is served by a CTA Brown Line stop and is two to four blocks from the city's major Metra commuter stations.

Putting debates about the merits of the site aside, there is little argument that it one of the Downtown area's prime locations, and perhaps underused by a squat, seven-story, 430,000-sf newspaper building with old printing presses in the basement. The Sun-Times' printing presses are now on the Southwest Side.

The Cook County Assessor's office places a $19.24-million market value on the property, but believes most of the value--87%--is in the land.

"The city of Chicago can only benefit from the redevelopment of that site," Whittington says."It's a great residential site. Office is not bad, but as a residential site, it's incredible, with those lake and river views," Hill adds.

Although Trump and Sun-Times officials met privately with Daley before announcing their plans, the city's planning process has increasingly included neighborhood involvement. Among the Sun-Times' neighbors are residents of multifamily buildings, some of whom would lose river, lake and Downtown views if a tower is built. The same thing happened to residents of Marina City's 60-story east tower when the IBM office tower was built. Whittington says he is not aware of any talks with department of planning and development officials, reiterating that it's still early in the development process.

Hill recalls Sun-Times officials quizzed city officials on the best uses for the site about two years ago during their search for a development partner.

Although the genesis of the latest proposal comes from a joint venture between Trump and Sun-Times parent Hollinger International Inc., one question is where the newspaper's staff will be located during construction, and perhaps after.

One possibility could be the proposed 505 N. State St. office tower one block north. John Buck Co. is talking with a few potential tenants, including one unidentified media company. US Equities also is providing tenant representation to the Sun-Times, and exploring all possibilities, Whittington says.