Bill Shanahan and Doug Middleton

Bill Shanahan (left) and Doug Middleton.

#88

Bill Shanahan and Doug Middleton

Chairman of New York capital markets; vice chairman in New York investment sales at CBRE

Last year's rank: 79

Bill Shanahan and Doug Middleton
By May 9, 2025 9:18 AM

Doug Middleton and Bill Shanahan know how to handle market volatility — and have the deals to prove it. 

Although 2024 started out slow, “it was a really, really good year,” said Middleton. Alongside Shanahan, he worked on transactions in the realms of student housing, ground lease restructurings, distressed office loan sales and straight residential deals, among others. “It was moving with the market and just being able to get transactions done,” he said.  

To have success in and beyond such a year, buyers need to have their full capital stacks ready to go, said Middleton. That way, there are no surprises. 

“Certainty of execution is paramount across all of this because deals are taking longer and the markets are volatile,” he said. “It’s really just keeping all the sellers educated on a day-by-day basis.”

Shanahan, meanwhile, underscored the importance of experience in both domestic and global markets. “The amount of data we have as to where capital’s going — what capital’s thinking about — that’s where we really provide an advantage to our clients,” he said. “Nobody else has that kind of intel. So, in a really choppy market like this, we tend to outproduce what would otherwise be market results.”

Of the duo’s accomplishments, Middleton singled out the $70 million sale of 636 Avenue of the Americas in September. That deal began as a distress sale for Clarion Partners, but evolved into a larger transaction for the whole building. As such, CBRE had to communicate with the retail condo owners, Nuveen Real Estate and Union Investment, and appease all sides. “It was putting the pieces together because A plus B was greater than C,” said Middleton.

CBRE likewise found opportunities within office-to-residential projects, such as 1011 First Avenue. Large conversion projects have been a subject of much attention, but it’s the smaller, sub-100-unit residential projects that are most likely to be the focus for future deals, Middleton said.

“With the volatility and potential tariffs, it’s going to be harder and harder to develop larger buildings,” he said. “Multifamily is going to be one asset class in New York City that, potentially, will not be as impacted as others.”

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