“The Most Complicated Deal I Personally Have Handled.”

Mr. Astrachan drew up a deal for Tommy Hilfiger to sublease 21,000 square feet of space back from Lord & Taylor, and Mr. Hollander and Mr.

Zarba arranged a 50,000-square-foot direct lease with RXR Realty for Harry Fox.

Then everything hit one last nerve-jarring speed bump.

The deal that Mr. Taubin was arranging downtown for Harry Fox collapsed. It was early November, two months into a fevered tangle of dealmaking. That elusive window in which everyone’s interests had finally aligned was closing. Mr. Taubin, however, had smartly arranged a backup plan at the Donald Trump-owned office building 40 Wall Street.

“After our first deal fell apart, we literally drew up a deal at 40 Wall Street in a week,” Mr. Taubin said. “The Trump Organization was incredibly accommodating. They really wanted us as a tenant in their property.”

Harry Fox ended up signing a 37,000-square-foot deal for 40 Wall Street’s entire sixth floor. Although the space is smaller than the office it leases at the Starrett-Lehigh Building, Mr. Taubin said the firm is able to house the same number of employees because its offices will be tailored to the company’s real estate needs.

“The space at Starrett Lehigh was great for HFA five years ago, but through a new build-out, we’re getting tremendous efficiency now,” Mr. Taubin said.

On the Thursday before Christmas, both Tommy Hilfiger and Dentsu inked expansion deals. Tommy Hilfiger will occupy approximately 350,000 square feet, and Dentsu will take roughly 170,000 feet.

“This was seriously the most complicated deal I personally have handled,” Mr. Hollander said. “Every deal has its posturing, but in the end, it worked because we all cooperated and worked together.”

“The Most Complicated Deal I Personally Have Handled.”