Like all great builders, Don Chiofaro wants to see how high he can go. Rocking on the bow of a harbor ferryboat as the sun sets, he points to the horizon, between Rowes Wharf and the Custom House Tower, and describes the tallest project the Boston waterfront has ever seen. His olive-green baseball cap, atop a full head of white hair and a permanently tan face, displays a single word—“Persistence”—a reminder of how far he’s come, and how long he’s been at war.

A Harvard linebacker turned developer, Chiofaro introduced himself to Boston 35 years ago with carnival flair and kinetic force. He walked into a City Hall meeting wearing his old Harvard jersey and blasting the Rocky IIIsoundtrack. He decimated a parking garage on Super Bowl Sunday 1985. Then he made a TV commercial of the implosion, announcing his plans to build Boston’s tallest building of the ’80s—International Place, a million-plus-square-foot office complex overlooking the Greenway that kicked off a new era in the city’s development.