Since 2000, the U.S. office market has witnessed a good share of trophy deals, which is usually a sign of strong market conditions. Using CommercialEdge data, the following is a review of the top 50 office deals of the last 20 years. Specifically, the report looked at office buildings of at least 50,000 square feet in size and mixed-use properties that have more than 50% office space (for further details, read our methodology). Additionally, the report highlights major deals in the Northeast, Midwest, South and West, as well as best-selling Class B office spaces and properties less than 250,000 square feet in size. #1 Office Deal of the Last 2 Decades: $2.8 Billion Sale of GM Building New York City occupies the first 12 spots within the list of top office deals of the last two decades – an unsurprisingly dominant presence in the ranking. As for office deals outside of New York City, only 11 transactions made the cut — with more than half of those being portfolio deals. The highest-ranking office deal from outside New York City was the $1.64 billion Century Plaza portfolio in Los Angeles. Sold by General Motors in 2014, the three-building portfolio totaling 3.3 million square feet placed 13th. Boston features four entries on the list, led by 500 Boylston and 222 Berkeley in 23rd place. EQ Office sold the 1.3 million-square-foot Boston office space to a joint venture between Oxford Properties Group and JP Morgan Chase in 2015 for $1.3 billion. Notably, several buildings were sold twice since 2000, fetching top prices each time. One such property is the General Motors Building in Midtown Manhattan, which also ranks as #1 office sale since 2000. Boston Properties paid $2.8 billion for the office tower located at 767 5th Ave. in 2008. The office tower had previously been sold in 2003 for $1.4 billion — landing it in 18th place for a second entry on the top 50 list. Another property with double entries in the list is the News Corporation Building, anchored by media giant Fox News. Located at 1211 Avenue of the Americas, its $1.52 billion sale in 2006 was the first sale to land it a spot on the list — in 15th place. Then, in 2013, Montreal-based Ivanhoe Cambridge acquired a 51% stake in the property for $855 million, enough to hand it the 50th position on the list. Highest-Ranking Office Deal of 2020 Falls Short of $1 Billion Mark for First Time Since 2012 In 2020, the $900 million sale of 330 Madison Ave. landed in first position, followed by the $810 million transaction of the former Master Printers Building — both in New York — and the $729 million sale of 245 Summer St. in Boston. It’s worth noting that the last time the leading office sale of the year was less than the $1 billion threshold was in 2012. At that time, Singaporean wealth investment fund GIC Real Estate paid $851 million for the 48-story 101 California in San Francisco. Likewise, the highest-ranking office deal in the West last year was the $664 million deal for the Transamerica Center in San Francisco, which was closed by a joint venture between SHVO and Deutsche Finance. In addition to the iconic Transamerica Pyramid, the transaction also included the 185,000-square-foot office building at 505 Sansome St. and the 52,000-square-foot property at 545 Sansome St. By comparison, Apex Capital Investments closed a $187 million deal last December for the 352,000-square-foot Grand 2 at Papago Park Center in Tempe — the priciest sale of a Phoenix office space for rent in 2020. Two other transactions of Tempe office buildings close out the ranking, trading for less than half of that amount: Discovery Business Campus – Northern Trust III for $65 million, and the Park Bridge and Park Garden at Fountainhead Corporate Park for $62 million. To the west, there was a much tighter race for the first...