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Whale Tales of Woe In A Sea Of Opportunity

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'Hey, what gives Curbed? I've gone whale-watching before and can assure you that's a breach not a flop.' Yes, technically that's right. But, as in luxury real estate, it's very hard to breach without flopping sooner or later. Enter the following capsule reviews of well-known Chicago whales and their real estate traumas:

Oprah Winfrey— While never short of real estate, Oprah probably wishes she'd never purchased her co-op at the Beaux Arts enclave at 199 E Lake Shore Drive. It was clear from Day One that she didn't care for the area's peeping toms. What would've been a six-year headache for almost anyone else (involving a failed effort at renting for $15K/month) may not have stressed out the Queen of gab all that much, but the $2.7M sale price was less than half what she spent on the 4,700-square-foot unit in 2006.

Antoine Walker— This case of confiscated real estate involves ex-NBA baller and Chicago native Antoine Walker and his self-built Tinley Park mansion. Facing huge debts, Walker lost the home to foreclosure in 2010. Chicago Mag's Dennis Rodkin had a gander last winter at foreclosure flip artist Mack Companies' transformation and re-listing of the garish 13,000-square-foot abode for $1.79M. That's less than half of the $4.1M Walker reportedly sunk into construction. You gotta feel for the guy.
R. Kelly— In late 2011, R. Kelly placed his 11,000-square-foot Olympia Fields mansion (some reports have the square footage at 22,000) on the market for just $1.6M. The events that prompted such a bargain basement offer included a $2.9M foreclosure lawsuit filed against Kelly for missing more than a year's worth of mortgage payments. Apparently, his willful intention in skipping payments was to prompt his lender to renegotiate the loan. That didn't work out so well, and thus the extremely low short sale price (indicating Kelly owes morton the property than it's worth). The controversial R&B icon (he of the golden shower) has had more successful escapades in years past, pocketing $2.25M off the sale of his converted Lakeview church mansion in 2002. See, even in real estate there's an equilibrium.

Rosie O'Donnell— Rosie didn't exactly suffer a monstrous real estate loss, but her impulsive Lakeview single-family purchase became a very quick sale at a slight loss ($147K) after her Chicago-based OWN Network talk show collapsed in cataclysmic fashion in early 2012. So you see, one compounds the other. And Rosie? She made for New York like a bat outta hell.

Billy Corgan— A perennial member of the Curbed Celebrity Real Estate heat map, more for real estate trauma than success, former Pumpkins' frontman and tea aficionado Billy Corgan has finally closed the book on an unwanted condo at the spectacular Patterson-McCormick Mansion. You see, Corgan mostly calls Highland Park home and had tried for more than four years to shed his Gold Coast digs. The thorny situation, involving efforts to rent it out, ended with Corgan taking a $100K loss over his 2002 purchase price. Along with inflation, you can bet other investments around the home contributed to a much bigger loss. But we hear the tea house is doing fine.

Some Dude in West Rogers Park— Some dude in West Rogers Park (reportedly a local developer) lost his golf course-adjacent, 12,000-square-foot colonial mansion to foreclosure after first listing the head-scratcher w/ indoor pool for $2.45M in April 2011. The ask dropped month after month, all the way down to $750K, before being plucked away and sold by the bank in September for $730K. This is an anomalous section of West Rogers Park, bordering Warren Park. The neighborhood isn't exactly littered with mansions, nor with seven-figure listings.
·Whale Week 2013 [Curbed Chicago]