Trophy properties in gateway cities were highly sought after in 2015, breaking records yet again. New York City saw what's believed to be the largest single-building trade in the city's history when SL Green Realty Corp. paid $2.285 billion, plus about $300 million in lease improvement costs, for 11 Madison Ave. The 2.3-million-sf office property was purchased from a JV of the Sapir Organization—which had bought the property from MetLife for $675 million in 2003—and the CIM Group. The CBRE investment sales team of Darcy Stacom and William Shanahan, with DLA Piper as counsel, represented the sellers, while Greenberg Traurig advised SL Green. A Fried, Frank, Harris, Shriver & Jacobson LLP team led by Jonathan L. Mechanic and Julian S.H. Chung helped to structure $1.4 billion of 10-year, interest only, fixed-rate financing for the buyers from a consortium of lenders including Morgan Stanley, Deutsche Bank and Wells Fargo.

One mile uptown, RXR Realty emerged the victor in a competitive bidding process, laying out $1.2 billion to buy the Helmsley Building at 230 Park Ave from a JV of Monday Properties and Invesco Real Estate. Yet the trade of the 34-story, 1.4-million-sf trophy building in the middle of Park Avenue wasn't a straightforward asset sale. Rather, it involved the sale of REIT interests, involving many different levels of complications and risks. On the legal side, Greenberg Traurig's Richard J. Giusto, Danielle Gonzalez and Michael T. Lynott, and Schulte Roth & Zabel's Julian M. Wise and Seth R. Henslovitz, represented the sellers. Harry R. Silvera of Gibson, Dunn & Crutcher counseled RXR. CBRE's Darcy A. Stacom and William M. Shanahan handled the sale.

Another mile up, a partnership of General Growth Properties and Jeffrey Sutton's Wharton Properties paid $1.8 billion for the Crown Building at 730 Fifth Ave., reportedly setting a per-sf world record for a single office building at $4,490 per sf. A Skadden team lead by Audrey Sokoloff and David Wolin represented Deutsche Bank AG as administrative agent and co-lead arranger (together with Morgan Stanley, Goldman Sachs and Citigroup) in the $1.25 billion that went toward the buy. It took just four weeks to structure the complex financing, which also included both mortgage and mezzanine funds.

Eastdil Secured marketed the asset for sellers Winter Properties and Spitzer Enterprises, which had bought the then-half-empty 26-story building for $94 million in 1991. Although primarily an office property, it's the approximately 100,000 sf of retail space along the world's most expensive shopping corridor that gives the Crown Building its appeal—and price tag. GGP and Jeff Sutton will own, redevelop, lease and manage the retail portion of the property, and it's expected that the 290,000-sf office component will be redeveloped into a luxury hotel and residential condos by the Doronin/Shvo group.

On the subject of hotels, early last year Hilton Worldwide Holdings Inc. sold the iconic Waldorf-Astoria New York for $1.95 billion to Chinese investor Anbang Insurance Group Co. Ltd., while retaining a management agreement to continue to operate the property for the next 100 years. Fried Frank, Skadden and Greenberg Traurig—with Jonathan L. Mechanic, Audrey Sokoloff and Robert Ivanhoe leading the respective groups—negotiated on behalf of Anbang. Hilton announced it would use the proceeds of the deal to buy more hotels in the US through 1031 exchanges.

And it did, a few weeks later when it bought a portfolio of Florida and California properties for $1.76 billion. The biggest in the package was the Parc 55 Wyndham San Francisco, a 1,024-room hotel in Union Square that traded for $530 million. The other properties, accounting for $1.24 billion, are all in Florida: the 1,001-key Hilton Orlando Bonnet Creek and 498-room Waldorf Astoria Orlando in Orlando; and the 150-room Reach and 311-key Casa Marina, both Waldorf Astoria Resorts in Key West.

Moving to Chicago, the sale of the Aon Center at 200 E. Randolph St. Downtown was eclipsed only by Blackstone's deal for the Willis Tower (see sidebar). The city's third-tallest building sold for $712 million ($260 psf), representing an impressive exit for Piedmont Office Realty Trust, which purchased it for $462.5 million in 2003. An innovative marketing strategy by JLL's Bruce Miller and Nooshin Felsenthal—with Piedmont's in-house reps Ray Owens and Tom Prescott—generated much interest in the 2.8-million-sf asset from both foreign and domestic players, resulting in 86 tours and 18 first-round offers. At the end, the winning bid came from the 601W Cos., which tapped a JLL finance team, led by Keith Largay, to structure a $630-million financing package from Bank of China and Blackstone for the acquisition and property improvements.

It wasn't only trophy properties—nor single-building sales—that garnered high price tags or interest from overseas buyers last year. Foreign investors were behind one of last year's huge industrial portfolio sales. Henley Holding Co., a subsidiary of the Abu Dhabi Investment Authority, and the Public Sector Pension Investment Board, one of Canada's largest pension investment managers, teamed up to buy a 58-million-sf portfolio of 209 core industrial properties in 25 key US distribution markets. The seller, Exeter Property Group, earned $3.15 billion in the deal. Eastdil Secured and CBRE marketed the portfolio on Exeter's behalf. Fried Frank's Christopher Roman and Lee Parks and Kelly Anne Donohoe of Silverang, Donohoe, Rosenzweig & Haltzman LLC advised Exeter, which invested in the joint venture and will also continue to manage the purchased properties. Kirkland & Ellis LLP, Davies Ward Philips & Vineberg LLP and Torys LLP served as counsel to the buyers.

In Honolulu, General Growth Properties Inc. entered into a 75%-25% partnership with AustralianSuper Pty. to own and operate Ala Moana Center. Soon after securing $907 million from AustralianSuper, GGP sold an additional 12.5% interest to TIAA. All told, the transactions value the property at $5.5 billion. One of the largest and most productive malls in the world with over $1,350 of tenant sales per sf, the center is comprised of 2.2 million sf of retail and office space and is undergoing a major redevelopment. Meryl Chae led the Skadden team representing AustralianSuper in the partnership formation. The deal marks the buyer's biggest single-property acquisition and first US deal.

After rejecting Simon Property Group's nearly $23-billion takeover offer, Macerich Co. capitalized some of its holdings by selling minority stakes in eight shopping centers valued at a total of $5.4 billion. GIC Pte. Ltd., the sovereign wealth fund of Singapore, took a 40% stake in assets in Oregon, Arizona and Texas, as well as two in California. For its part, Heitman gained 49% ownership of a mall in New Jersey and two in Colorado.

Macerich expects to realize cash proceeds totaling $2.3 billion from the two JVs. Its team included Manatt, Phelps & Phillips LPP's Tom Muller and Anita Sabine; Philip C. Sutton of PriceWaterhouseCoopers; Edward L. Glazer of Goodwin Procter LLC; and DLA Piper's Michael D. Hamilton. Brian T. May and Jessica M. Waller of Mayer Brown served as legal advisors to Heitman. GIC was advised by Nancy M. Olson, Karen M. Lee, Jonathan Friedman and Evan Levy of Skadden.

Big prices were paid for retail assets, with the largest per-foot figure coming in at $4,565. That's how much Vornado Realty Trust paid to Starwood Capital Group and Crown Acquisitions for the 78,000-sf Old Navy Flagship Store in Manhattan's Herald Square. Leased to the retailer through 2019, the site also comes with 226,000 sf of additional zoning air rights. The REIT helped to meet the $355-million purchase price with a $205-million loan from Morgan Stanley. Incidentally, Vornado was also behind the city's largest retail lease, a 63,780-sf space at 640 Fifth Ave. for Victoria's Secret.

Akerman LLP handled one of the largest retail deals in Miami-Dade County history when its represented Playa Retail Investments LLC in its $370-million acquisition of a 1.1-acre block of Miami Beach's Lincoln Road. The price tag factors out to $4,900 per sf of retail space and $7,700 per sf of land. Akerman's Manny Fernandez, Carol Schoffel Faber and Kathryn A. Goldberger represented the buyer. The sellers, Fryd Properties and Comras Co., were advised by HFF's Manny De Zarraga, Daniel Finkle and Luis Castillo.

It wasn't an investor, but a tenant, that dug deep into its pockets in our next deal, involving 11,500 sf of Beverly Hills retail space last year. Exercising its right of first refusal after another investor submitted an unsolicited offer, Chanel paid $152 million for its 400 N Rodeo Dr. digs, factoring out to a whopping record $13,217 per sf. Private practice attorney Ron R. Goldie organized and structured the transaction for owner Rodeo Brighton LP and the sale was additionally handled by Elkins Kalt Weintraub Reuben Gartside LLP's Scott Kalt. Greenberg Glusker's Dennis Ellman also advised Rodeo Brighton. Chanel was represented by Ballard Spahr and Scott Pearson. The luxury retailer plans to join the purchased space with a store it owns next door to create a larger footprint.