A skyscraper that would rival President Donald Trump’s Chicago high-rise as the city’s second-tallest would emerge behind the historic Tribune Tower, while the neo-Gothic office building would be turned into condominiums under still-evolving plans described by an alderman and two sources familiar with the proposal. Envisioned as a hotel and condominium tower sheathed in steel and glass, the new skyscraper would soar to a height of 1,388 feet, downtown alderman Brendan Reilly and a source familiar with the plans confirmed. That would be a foot shorter than the hotel-condo high-rise that Trump, then a real estate developer and reality TV star, completed in 2009. Tribune Tower, whose flying buttresses and pinnacle-topped crown have long made it a symbol of its namesake newspaper, would be turned into condominiums, Reilly and two sources said. The tower’s upper floors are already being gutted. The plans, drawn up for the owners of the Tribune Tower property – CIM Group of Los Angeles and Chicago-based Golub & Co – are expected to be presented to the Chicago Plan Commission by this summer. If the developers win city approval and obtain financing for the mega-skyscraper – by no means a sure thing, as the saga of the never-built 2,000-foot Chicago Spire attests – it could be a political plus for Mayor Rahm Emanuel, who regularly touts the flock of construction cranes dotting the city’s skyline as a sign of economic strength. However, the plans also pose some political peril if they anger neighbours of the new high-rise whose views would be blocked. And historic preservationists could object to the plans on the grounds that the new skyscraper, which would be roughly three times the height of 36-storey Tribune Tower, would dwarf the historic building. The skyscraper would rise on the north side of what is now a car park behind Tribune Tower. A call and email to Lee Golub, executive vice-president of Golub & Co, were not returned last Wednesday night. Under the developers’ current plans, Tribune Tower would be redeveloped over a three-year period, followed by the erection of the new skyscraper, a source confirmed. Reilly said he has seen “several iterations” of renderings for the new building, describing it as a thin and soaring structure, but was still waiting to see the architects’ final submission. Designs for the project have not been publicly released. “It’s gone through quite the evolution, and I think each tweak has improved the proposed design, but I know for a fact they’re not done yet,” said Reilly. “I’ll reserve comment on its design until they send over their best foot forward.” In 2016, CIM Group and Golub & Co bought the Tribune property from Tribune Media, a broadcasting concern, for US$240 million. In addition to Tribune Tower, the property consists of three low-rise structures – a former printing plant, the four-storey WGN Radio building and the 11-storey WGN TV building – that connect to the iconic skyscraper. Most of Tribune Tower’s exterior and its main lobby – a hushed, churchlike space whose travertine marble walls are inscribed with quotations about freedom of the press and courage in battle – are protected by the city landmark status that was granted to the building in 1989. Although the other buildings in the Tribune complex do not have protected status, their facades are likely to be preserved under the redevelopment plan, Reilly and a source confirmed. The Emanuel administration has been receptive to the size and scope of the project, including building what would become one of the city’s tallest structures on the site, according to a source with knowledge of the discussions between City Hall and the developers.