Is Jack Connors the Last King of Boston?

IT’S VERY HARD NOT TO BE WOOED by Connors in his office. First, there’s the literal heights he’s attained. The office sits on the 60th floor of the Hancock Tower, in the space formerly occupied by the skyscraper’s observation deck. What was once a stop for gawking tourists is now a cavernous space for this, the last phase of Connors’s career, which he carries out under the name of the Connors Family Office. Then there is Danielle, one of Connors’s two secretaries, who knows who you are before you state your name. “Jack is on a call but will be with you shortly, Mr. Kix.”

Then there’s the office itself. It’s accessed through a foyer that could probably house its own company, which leads to a room that’s glass and sunlight and open sky; that’s really all you see for a while, all around you. And that’s when Connors takes you, blinking against it all, and leads you to the far wall. “See that over there?” he asks, pointing south toward some inscrutable office complex. “That’s Faulkner Hospital. That’s where I was born. And that,” he says, pointing farther south now, “that’s Roslindale, where I grew up.” And then he describes his childhood: the son of second-generation immigrants, a father who worked for a company that managed the heating and air-conditioning units in hospitals and schools, and a mother who worked as a secretary. They weren’t poor exactly, just on the lower end of the burgeoning middle class.

“Come over here,” he says. He leads you to the other side of the office, looking down on Back Bay and the Charles River and Cambridge beyond. “Over there is Boston College,” he says, pointing west to where he went to school. “Come a little bit closer and look down.” He points almost straight down. “That’s Newbury Street. And that building right there” — a gray, slightly Gothic, six-story thing — “that’s where we got our start.” Connors cofounded the ad agency Hill, Holliday, Connors, Cosmopulos when he was 25 years old, in 1968. The firm had such bright prospects that cofounder Alan Holliday left within a year. Still, by 1980, the agency had moved its offices into the Hancock Tower. Success — booming success — followed. By 1998, Connors, the only remaining founder, sold the agency to the Interpublic Group. (Connors’s stake was a reported $115 million in stock.) And now, Connors says, “Here I am,” 21 floors above his old office, an un-encumbered view of his city, the whole narrative of his life right down there.

“Pretty cool, huh?” And it is. To see this aging man looking down, squinting at all those memories, sharing this bit of himself, of who he was and has since become, creating a sort of intimacy that’s hard to fake or forget.

 But then, maybe a couple of weeks later, after you talk about Connors with some local dignitaries, say, Ophelia Dahl at Partners in Health, you start to notice something. They mention the first time they met Connors in his office. And the details are exactly the same. “There’s Roslindale. The building right there, that’s where we got our start.” And you realize: My God. He does this for everyone.

“Oh, yeah,” D’Alessandro says. “Jack’s like an Irish Frank Sinatra. He knows a good tune when he hears it, and he’ll sing it again and again.”