Is Jack Connors the Last King of Boston?

After Sister Gail finished, Connors said, “If you don’t mind, I’d like to speak with these gentlemen in private.”

This was not the first time Connors had talked with Tucci and Kelly about the academy. Two years prior, he had taken the men to lunch to explain the school. Six months after that, he had given Kelly a tour of the building as it was being refurbished. He knew the effect the school would have on the men. Neither was born into wealth. Both understood what an education offers. And now here they sat, Connors explaining that he wanted to raise $70 million for these academies, and how he was almost there. He said the work the school was doing was extraordinary — so extraordinary that he and his wife had given millions of their own money. Now it was time for Kelly and Tucci to consider what they could do.

A few weeks later, he heard back from them. They’d give $1 million each. “Because of Jack, it was an easy give,” says Kelly.

Sister Gail nearly fainted when she heard the news.

ONE OF THE WAYS Boston is different from many cities is that it doesn’t have a single base of economic or cultural power. It’s not like Miami with real estate, or Houston with oil, or L.A. with entertainment. In Boston, there are five sectors that are the primary drivers of the city’s economy and culture: healthcare, higher education, tech, finance, and politics. And the symbiotic relationship these sectors have with one another is unique. (New York’s fashion industry doesn’t really need Wall Street, for instance, but here, Brigham and Women’s Hospital very much needs the students at Harvard Medical School, and vice versa.)

No one has navigated those sectors better, or longer, than Connors. For 29 years he was the head of what would become the largest ad agency in Boston, Hill Holliday. For the past 14, he’s been chairman of the board at Partners HealthCare, one of the state’s most important and largest employers. He sits on Harvard Medical School’s Board of Fellows, and on the board of Boston College. Part of the reason he’s been on those boards, and those of more than two dozen other corporate, civic, and nonprofit organizations over the years [see sidebar on page 109], is that he is this city’s fundraiser nonpareil, a genius at separating very rich people from very large sums of money.

This year Connors helped relaunch the Vault, which was once the most powerful lobby for business interests on Beacon Hill, and may be again. He’s also attempted to buy the Boston Globe (twice). He knows Speaker of the House Nancy Pelosi and has chatted with President Obama. The number of people who call Connors’s office every day — asking for advice, for favors — can reach 100.

In a city known for its transcendent Irish figures, Connors is the first to grab and hold power not by dint of political muscle (à la James Michael Curley), or by the scourge of a brutal reputation (Whitey Bulger), but by the art of enchantment, by all the mementos and birthday wishes and bullshit sessions that leave his targets enamored and indebted to him, too.

But just as there will never be another Curley or Bulger, there will never be another Connors. The tribalism that defined Boston for so long — where your grandparents were from, where you grew up, all the stuff Connors intuitively understood and exploited and which made him so much money — no longer counts for much.

Connors may be the last identifiable Irish-Catholic to run Boston, not because he will be the last Irish-Catholic to hold considerable sway within the city, but because the public won’t care that the next great Irish-Catholic is, in fact, Irish-Catholic. And yet today, in so-called retirement, Connors is more influential than ever. If he is the last of one era, he is also the first of another, more evolved one.