“That transaction took two years to complete,” Rafaeli says. “When you have a sale that takes so long to finish, and you’re dealing with such big numbers, you want to make sure that everything is right for everyone concerned.”

For Rafaeli, the completed deal marked his most rewarding sale of 2014, a year that saw the Coldwell Banker agent close $109 million in transactions, up from $45 million in 2013. Rafaeli represented Trump Tower and the seller in the transaction, but his interest is to connect the right people to the right property, and to make the best deal possible so that everyone walks away happy.

“The deals I do are very large,” he says. “I spent all of 2013 working on some of these transactions that didn’t get finished until the next year.”

The process was one of multiple meetings, meals and discussions of how Shah envisioned the unfinished space taking shape. For Rafaeli, who managed to represent both sides through networking and his sphere of influence, completing a deal is as much about getting to know the client’s needs as it is about finding the right price point.

The Trump Tower sale was not Rafaeli’s first high-profile deal in Chicago. The former New Yorker, who moved to Chicago 14 years ago, also handled Citadel CEO Ken Griffin’s $15 million purchase of a Park Tower condo penthouse in 2012.

Rafaeli’s patience and his willingness to work over every step of a deal with a client helped him close the deal with Shah, but sometimes clients need a bit of a push to see the way through to completing a purchase. He coaches them in their decision, letting them talk out the pros and cons of a particular property and offering advice when they need it.

“Some people need a little encouragement,” he said. “You almost have to tell them to make the deal. Otherwise, they may never make a decision. Sometimes, that’s my role.”