Is Jack Connors the Last King of Boston?

CONNORS AND HIS PARTNERS founded Hill Holliday after leaving the Boston office of New York ad giant BBDO. Two of the guys were creative types; Connors was the self-described “peddler.” To put himself through BC — he was the first in his family to graduate from college — Connors sold peanuts and scorecards at Fenway, drove a cab, and served six months’ active duty in the Army National Guard, though this last bit had more to do with supporting his older sister, Peggy, whose husband had walked out on her and her three children when Connors was a teenager.

At Hill Holliday, he became president. He needed to make some money; there was Peggy to support, and he was married with his first child, too.

The partners’ timing couldn’t have been worse. They had launched the agency when New England Telephone’s union went on strike, which meant they couldn’t get their phone system installed. Connors had to make every business call on a pay phone just outside the office until the strike ended. Things didn’t improve after that. Boston was a regional marketplace in the late 1960s, crowded with about 10 ad agencies, and Connors couldn’t get access to any executives. So he came up with an idea: He’d sit on the boards that CEOs sat on, volunteering Hill Holliday’s services for nonprofit campaigns. The hope was that the CEOs would look at Hill Holliday’s pro bono work and say, “Why aren’t we hiring them?”

That’s pretty much what happened. The agency grew despite the quick departure of one of its founders and the youth of its president. Connors came to see the power of nonprofits. By sitting on enough boards, he realized, he could get in front of anyone. And once he was there, well, maybe he’d ask about the CEO’s family, or tell a joke about the different universities he and his Brahmin cofounder Jay Hill had attended: “Jay went to a school where carved over the front door was the phrase E pluribus unum. I went to a school where spray-painted over the front door was the phrase ‘Vito sucks.’”

John Verret, who would go on to become Connors’s chief rival as president of Arnold Worldwide, took a job with Hill Holliday in 1975. Back then, the culture of the place was intense and ambitious, a style befitting its president. “I’d go to work at 7 and leave on the 9:45 train at night,” Verret says. “The energy of that place was something to behold.” Still, Verret didn’t see his kids for the first two weeks he worked there. One day he told Connors that his situation was untenable, that his wife was unhappy.