The plight of Chicago’s two largest office buildings detail the still raw difficulties of commercial real estate outside of the current US core markets of Washington, DC, New York City and to some extent, San Francisco and Texas cities.

At the tallest office building in the country, the Willis (former Sears) Tower, property managers are fighting for a contract to lease a structure that’s dropped about 10% vacancy in the past two years to just more than 80% full – a gap of about 800,000 square feet. The tower owners, American Landmark Properties Ltd. and a couple of New York City investors, recently had to postpone a $1.5 billion offering for the 110-story building due to lack of buyers.

The problems are worse over at the 100-story John Hancock Center, as the ownership partners Goldman Sachs and Golub & Co. have fired off both a plea and a warning to their lenders – give us an extension of our $400 million loan that’s due next week – or else. The companies have said through attorneys that they will fight in court to keep control away from CMBS and debt owners, in a maze of tranches that at one time (but no longer) included now-bankrupt Lehman Bros.

Distress can come in many different forms, from problems with a fickle tenant-led leasing market for the Willis, to Hancock’s case, where the partnership is judged to have spent too much ($383 million) for the tower in 2007. The European debt crisis, which crushed many comeback hopes in the third quarter last year, didn’t help.

Boiled down, the plight of these two high-profile towers isn’t much different than the rest of the struggling properties throughout the Chicago area, and through the Midwest.

Barry Missner, president of the self-named Skokie, IL-based Missner Group, has been handling dozens of receiverships for the courts for office, industrial and other properties throughout Chicagoland, particularly in the more than 20% vacant suburbs. He says he’s seen all sorts of ways for sites to go bad. “There’s just not a clear correlation that you can point to and say, ‘That’s what caused these problem properties’,” Missner says. “Values everywhere went down.”

However, the light at the tunnel may be coming, he says, when you can see banks finish up dealing with their top problems, and properties that were a problem start turning the corner. The dearth of quality bulk office space has spurred some action in downtown Chicago, such as at the former IBM Building on State Street in River North.

After suffering from the departure of its namesake years ago and by losing some of its Lake Michigan views to the new Trump International Hotel and Tower, Prime Group Realty Trust (which is fighting its own takeover battle by Five Mile Capital Partners) has managed to grab the American Medical Association and SmithBucklin to move their headquarters to the building. The AMA will anchor the tower with 300,000 square feet, and will rename it AMA Plaza.

It seems that most investors, owners, tenants and even brokers are stopping to pause this first quarter 2012, waiting to see which way the wind will start blowing. Local giant Jones Lang LaSalle, in its fourth quarter report Tuesday, touted record revenue gains of $3.6 billion – but also announced a temporary global hiring freeze.

Here’s to hoping that in 2012, some of the breezes of market success from the East will start blowing our way.

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