10 Big Commercial Real Estate Busts

Loan balance: $3 billion

Size: N/A

Location: New York, N.Y.

2. General Motors Building

New York City real estate mogul Harry Macklowe proved that in the world of commercial real estate, there can be too much of a good thing. In 2007, he scooped up seven Manhattan office buildings from private equity giant Blackstone Group, with the hopes of dramatically expanding the size of his real estate empire.

However, the loans used to make those purchases became nearly impossible to refinance once credit markets started to freeze up shortly thereafter. As a result, Macklowe’s firm was forced to sell off some of those properties, including what perhaps was his most prized trophy: the General Motors building, a 50-story white marble landmark with breathtaking views of New York City’s Central Park and home to iconic toymaker FAO Schwarz as well as Apple’s flagship Fifth Avenue store. At least it wasn’t all for naught — Macklowe more than doubled his investment on the building after purchasing it for $1.4 billion in 2003.

3. Treasure Island Hotel Casino

It wasn’t swashbuckling pirates that ultimately brought Las Vegas icon Treasure Island to its knees. Rather, last year’s distressed sale of the casino and its accompanying 2,885-room hotel was a necessary sacrifice for its former owner MGM Mirage.

Struggling with a difficult economic climate and hoping to raise some quick cash for its ambitious cross-town City Center venture, the casino operator sold the resort and its famous pirate battle display last March for a mere $775 million. Scooped up by Kansas billionaire Phil Ruffin, various estimates have placed the site’s replacement value at nearly four times that amount at $2.7 billion, according to commercial real estate research firm CoStar Group.

4. John Hancock Tower

Boston’s John Hancock Tower might just represent everything that went wrong with the broader U.S. commercial real estate market. Relying on massive amounts of financing, an ambitious New York City-based investment firm scooped up New England’s tallest office building in 2006 for an eye-popping $1.3 billion, betting that Boston’s office rental market and commercial property values would continue to remain red hot.

What they never anticipated, like so many other real-estate speculators, was the precipitous decline in property values and a spike in the nation’s unemployment rate to above 10%, which drastically weakened demand for office space across the country. Unable to service the debt load, the property was sold in a foreclosure auction last March for less than half of the original purchase price.

5. Universal City Plaza

When the Hancock Tower stumbled, so did Universal City Plaza. Sold together as part of a portfolio of foreclosed holdings last March, the property became one of the more high-profile casualties of the Southern California commercial real estate market since the start of the recession.

Home to a number of media and entertainment companies, including NBC Universal and Universal Music, the 36-story building and surrounding land is now jointly owned by a pair of East Coast distressed investment firms.

6. Canyon Ranch

In the world of commercial real estate, history does sometimes have a habit of repeating itself. For years, the Carillon Hotel was a fixture of the Miami Beach scene, only to be shuttered in the late 1980s as a result of a tough economic climate.

After a massive overhaul, the property reopened in 2008 as a hotel-condominium combination under the banner of Canyon Ranch, a well-respected name within the wellness community. That venture however would stumble yet again as a result of the recent economic downturn. Last fall, its developers handed over the remaining 300-plus unsold condos to its creditors.

Despite that hiccup, the Canyon Ranch development appears to be moving full steam ahead. More than 60 units have been sold since May and another 20 contracts are waiting to be completed, according to its current owners.

7. Pearson Building

While the loss of the General Motors building was mostly a reputational setback for Harry Macklowe, the impact of his company’s foreclosure sale of the Pearson building in Midtown Manhattan was a severe financial blow.

Unable to service its mortgage debt, the company lost the building in an auction last June to Otera Capital, a division of one of Canada’s biggest pension funds. The Canadian firm paid $241 million, according to CoStar Group. That’s less than half of what Macklowe Properties bought it for in 2006.

8. Maui Prince Resort

Metropolitan office buildings haven’t been the only ones getting squeezed by the fallout in the commercial real estate market. Resorts and hotels across the country have also been hit hard. In fact, recent figures published by research firm Trepp revealed that delinquency rates within this segment are leading the industry.

One particularly notable tale has been that of the former Maui Prince Resort, a spectacular 1,800-acre resort at the foot of Mount Haleakala that boasts 310 rooms and a Robert Trent Jones-designed golf course. An investment fund run by Morgan Stanley teamed up with a local firm in Maui to buy the property in 2007 for $575 million with the hope of developing it. Those plans quickly unraveled however as tourism to the state took a severe decline as a result of the recession.

9. Resorts Casino Hotel

When it expanded its operations in 1978 to include gambling, Resorts earned the distinction of becoming Atlantic City’s first casino. Its position as the granddaddy of the New Jersey gambling circuit hardly insulated the property when the economy tanked. Faced with fewer visitors and declining gaming revenues, Resorts’ mortgage troubles started to mount in late 2008. By the following fall it was embroiled in foreclosure proceedings, before finally handing over the keys to its lenders late last year.

10. The Watergate Hotel

Even landmark pieces of U.S. political history have not been spared by the commercial real estate fallout. Part of the residential-office complex that ultimately led to President Richard Nixon’s resignation, the Watergate Hotel went into foreclosure last summer after its owner defaulted on a $40 million loan.

The borrower’s original plans of refurbishing the 251-room luxury hotel however may still indeed happen. A messy legal fight over the hot