Is Jack Connors the Last King of Boston?

How Jack Connors rules by the art of charm.



What a group. That’s all Sister Gail Donahue could think. For 49 years she’d been a teacher and administrator at Catholic schools in the Boston Archdiocese, and now to have two well-known business leaders — Liberty Mutual’s Ted Kelly and EMC’s Joe Tucci — sitting across the table from her, here in her teachers’ lounge? I’ve read their names in newspapers, she thought. Wait till the sisters hear about this.

The man who had organized the meeting stood behind Sister Gail on that October day in 2009, wearing the preferred outfit of his nominal retirement: crisp white shirt, tie, gray pants. At 67, Jack Connors still moved with the insouciance of the self-assured. His hair was white but not so wispy that he couldn’t still part it; his shoulders remained broad, his build slim, his cheeks forever ruddy, as if he had just finished laughing at a joke he’d made.

Connors told the men how, four years earlier, Archbishop Seán O’Malley had said that some of the archdiocese’s schools were under threat of closure. The Archbishop had asked if there was anything Connors could do to help. Connors could do a lot. He not only raised millions; he also altered the way the archdiocese thought about schools. Why should neighboring parishes compete for the dwindling number of parents interested in a Catholic education for their children? Why not pool resources and build parochial academies?

This school, Pope John Paul II in Dorchester, was one of four such academies the church had built. Outside was only a mangled stretch of Columbia Road, but inside, as Kelly and Tucci had just seen on a tour, were refurbished floors, clean halls, bright rooms, and children of every color, religion, and income level.

What Connors needed now, he said, was for his guests to consider their own education, and how they had benefited from it. The room went quiet. He then asked the campus’s principal, Claire Barton Sheridan, and Sister Gail, its director of guidance and health, to speak. When it was Sister Gail’s turn, she cited what the money Connors raised had provided: books that weren’t 22 years old, hot meals, an office that handled tuition so that she and her fellow teachers could, well, teach. The academy teaches what she and Principal Sheridan like to call the “whole child.” Though the school has standard hours, the building’s doors are open from 6 a.m. to 6 p.m., which gives harried parents a chance to keep their children off the cruel streets, and gives their kids a place to learn about gardening, or physical fitness, or music. Ninety-seven percent of students in the Boston Archdiocese go on to college.

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, 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.

The luminaries who dominated the city during Connors’s lifetime — Billy Bulger, Tip O’Neill, Ted Kennedy — were all politicians. In a way, Connors is one, too. He’s always approached the city’s corporate culture as a ward boss might his constituents — by getting in front of as many people as possible.

From there it was just a matter of building relationships. Connors was never an ad man per se. He’s the first to admit he knows nothing about creating a good ad. But like a good politician, he could sell himself. And once people bought that, he gave them even more than he promised. He gave them his time and, as the years progressed, his myriad connections. His longtime friend and former client, one-time John Hancock CEO David D’Alessandro, puts it this way: “He got close to people and then he realized that what interested executives were their own careers, the charities they gave to, their families. And he would always find a way to get close to those issues.… Jack kept some clients longer than anybody else ever did. The work was good…. The work was fantastic. But you can get that work from somebody else. But you don’t let them go because you need Jack. Jack helps your career. Helps your family.”

This practice of intervening — for the greater good, for Connors’s own (for both) — has been a hallmark of his career. His relationship with D’Alessandro is a case study in Connors’s blurry line between good deeds and good business. John Hancock had been a Hill Holliday client for a couple of years when D’Alessandro’s mother died in 1986. D’Alessandro told no one but his boss, and drove the four and a half hours to upstate New York, where he’s from. There were two wakes for his mother, one in the afternoon and another in the evening, and in between D’Alessandro went with two of his aunts to a local Italian restaurant.

There, sitting at the bar, was Connors. He’d called D’Alessandro’s office earlier that day and coaxed his secretary into revealing the reason D’Alessandro was out of the office. Connors rented a private plane and had the pilot land in a nearby airfield. For two hours at dinner, Connors sat between D’Alessandro’s two aunts, making them giggle at his stories. “He took this pressure off of me, having to deal with my mother’s death,” D’Alessandro says. He never forgot it. Neither did his aunts. For years they asked D’Alessandro about the “nice Irish man.”

Such behavior wasn’t the only reason Hill Holliday kept the Hancock account. In fact, “That’s only one of maybe 100 things that have happened between us,” D’Alessandro says. Nor is the funeral story really remarkable. Says Connors’s friend Dennis Farrington, “Jack’s a professional mourner, a professional wedding attender.” But it shows how Connors puts in the time — because he wants to, yes, but also because he knows it means people are more likely to listen to him.

Take his role in the passage of the state’s universal healthcare bill. In mid-March 2006, the bill seemed dead. Speaker of the House Sal DiMasi wanted to implement a payroll tax for companies that refused to offer their employees insurance. DiMasi’s idea of a fair tax was $600 per employee. The business community wouldn’t budge above $62 an employee. Connors called DiMasi’s office one morning and asked if he could come by for a visit.

Connors had a vested interest in this visit, of course: Partners HealthCare would benefit handsomely from a bill that mandated every person in the state have insurance. But Connors’s ego is as great as his ambition; he knew he could play a decisive role in the bill’s passage, and didn’t want a deal to be frittered away on something as pedestrian as a payroll tax. The next morning he walked into DiMasi’s well-appointed State House office carrying a copy of Animal House.

He slid the disc into a DVD player; the movie was cued to a scene where John Belushi’s character demands that Delta House not quit in the face of Dean Wormer’s evil machinations. “Over? Did you say, ‘Over’? Nothing is over until we decide it is! Was it over when the Germans bombed Pearl Harbor?! Hell no!… And it ain’t over now!”

DiMasi chuckled. Connors turned to him. “With all due respect, Mr. Speaker,” he said. “Nothing is over until I say it’s over.”

Connors returned to his office and opened his Rolodex. He organized meetings among business, insurance, and Partners executives. Then he went to good-government types, like the Massachusetts Taxpayers Foundation. Four days later, Connors met with DiMasi again.

We have a compromise, Connors said. The business community would do a tax of $300 per employee. DiMasi liked it. Later that year the bill was signed into law. And lest anyone think that Connors was one to downplay his contribution, there was the dinner he hosted a few nights after the bill’s passage. About 20 people attended, including Governor Romney’s key staffers, several powerful business executives, and DiMasi. After the dinner, Connors gave everyone a gift. Many were small Steuben glass figurines that served as a metaphor for each person’s role in the bill. But Connors gave the last gift, the largest gift of all, to himself: a two-foot-tall peacock.

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.”

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.

That night Verret came home to a house full of flowers. His wife, Meg, had tears in her eyes. The note on the flowers read, “Meg: I don’t think we’ve given you the proper introduction to Hill Holliday.  — Jack Connors.”

In part, Connors gave the flowers to Verret’s wife for the same reason that, after hiring many ambitious women at Hill Holliday in the 1980s, he set up in-house daycare: He would do whatever was necessary to keep talented people. But there have also been gestures so large, that cost Connors so much, that explanations of self-interest aren’t really sufficient.

In the 1970s Hill Holliday had an art director named Paul Collins. Collins’s father was in the restaurant-supply business. That business went bankrupt, and Collins’s dad had used the family home as collateral — the family home that Collins and his wife and children were then living in. One day at work Connors noticed that Collins seemed particularly glum. Connors kept hounding him about it until Collins said, “My house is going on the auction block.” Come next week, Collins said, he didn’t know where his family would live.

The morning of the auction was cold, with a bit of rain. Connors arrived without a trench coat, and his suit was soon soaked through. He watched as the auctioneer began the bidding at $15,000. As the bidding approached $25,000, Connors looked around; Collins’s two kids were peeking out a front window, watching their own eviction. Connors knew he had to get the house. He threw up his hand again, the other bidder backed off, and the auctioneer banged his gavel. He handed Connors the key. Then Connors walked up and handed it over to a befuddled-looking Collins. “It’s yours,” Connors said. Though the agency didn’t have a lot of money in those days, Hill Holliday would write it off as a business expense, and Paul Collins and his family would stay in their home, making an easy monthly payment. Connors still keeps in his office a key from Collins, a gift with the inscription, “Jack: Our home is your home.”

On a recent July morning, Connors stood in the doorway of Charlie’s Sandwich Shoppe on Columbus Avenue. “Jack,” said Marie Fuller, who’s been a waitress at Charlie’s for 44 years. Connors walked over, so eager to kiss Marie’s cheek and shake the hand of her brother, Charlie’s co-owner Chris Manjourides, that he didn’t take off his sunglasses until Marie guided him to his seat.

Marie and Chris are two of the four members of the Manjourides family who operate the restaurant. They say they’ve never had a customer quite like Connors. He’s the only one to send a Christmas card every year. He also knows details about each of the four brothers and sisters who run Charlie’s, and always takes time to ask about them. On this day, he took a seat and looked at the photo from Disney World that hung on Charlie’s back wall. It was a shot of the Manjourides family celebrating their restaurant’s 80th anniversary. “How are you doing — all 27 of you or however many there are?” Connors asked.

Marie Fuller smiled. Three years ago, when she was planning the vacation, she got a call from Connors. He knew about the getaway — how, she doesn’t remember — and said that he wanted to help.

“No, Jack,” Fuller had said. But there was no dissuading him. He knew a guy at Disney and had already arranged for the entire family to have VIP treatment during their vacation. No need to wait in any line. Reservations at any restaurant. It would be his treat. The shot of the family at Disney World hanging on Charlie’s back wall? A reminder of “just how special” that trip for the Manjourides family had been, Fuller would later say.

And so, three years later, on that warm July morning, when Connors looked up at the photo and asked how the family was doing, Fuller not only smiled, but her eyes moistened a little. “We’re fine, Jack.”

She then brought him his water and told him it was okay if he parked out back, in the spot marked for family.

Generosity alone has never defined Connors, however. At Hill Holliday he was ruthless with competitors, taking business away — stealing it, really — based on connections that no one could rival. In the early 1990s, Fran Kelly, now the vice chairman of Arnold, worked for a Rhode Island agency that counted Cambridge software company Lotus Development as a client. Lotus brought in a new chief marketing officer, a guy with a very Irish name: Mark Flanagan. As soon as they found that out, Kelly’s colleagues began kidding him: It’s only a matter of time now before Connors goes after Lotus.

That’s exactly what happened. Because of Connors’s rapport with seemingly every guy named Flanagan, Sullivan, McDonough, or, hell, for that matter, Kelly, Kelly’s agency lost Lotus to Hill Holliday, which led Kelly to eventually join Arnold. “I like Jack; I respect him,” Kelly says. “But, you know, there’s a really steely side to him.”

Connors’s employees saw it, too. Many endured “Jack Attacks,” which became so legendary in business circles that Fortune magazine once named Connors one of “America’s Toughest Bosses.” Give him a bad projection and Connors might kick the chair of the offending employee. Or he might scream loud enough for the whole office to hear. Whatever the case, Jack Attacks were so commonplace that “one year at a Christmas party, we wrote a song about it,” says Peter Rizzo, who worked at Hill Holliday in the 1980s. It was set to the Rolling Stones’ “Jumpin’ Jack Flash.”

In that era, Fenway Franks was a Hill Holliday client — a very demanding one. One Friday, Connors received an angry call from Fenway Franks CEO Jack Satter, describing how John Verret, the man on the account, had screwed up. Connors called Verret into his office, seething. “For what you’re making I could get a line out the street,” Connors screamed. “If I wanted to hire assholes, I could hire three assholes to do your job!”

Verret tried to explain that there had been a simple misunderstanding. But Connors wouldn’t listen. Finally, Verret said, “Fine, Jack. Just do what you want.” He got up to leave the office.

“You’re goddamn right I’ll do what I want!” Connors replied as Verret walked out the door.

The next day, a Hill Holliday staffer was getting married. Verret and his wife walked into the church just ahead of Connors. Waiting to be seated, Connors tapped Verret on the shoulder. “Could you forgive a certain asshole for the way he treated another asshole?”

Still, it was his charm — even more so than his intensity — that helped Connors transform the company. In 1980 Hill Holliday found out that Wang Laboratories, the company with the first successful word processor, was looking for an ad agency. A secretary for Wang executive John Cunningham called Connors one day to say that Cunningham had heard a speech Connors gave at a career-counseling seminar at BC. Impressed, Cunningham wanted Connors and Hill Holliday to bid for Wang’s business. Connors was thrilled, but he also knew he had made no such speech. He showed up at Cunningham’s office in Tewksbury anyway, only to have Cunningham realize Connors was not the guy he’d heard at BC. The secretary had contacted the wrong executive. Connors, not wasting the opportunity, sat Cunningham down and started talking. You’re Irish, too, how about that? And where’d you say you grew up? Well, that’s only a mile and a half from me. Soon, Cunningham liked Connors more than that guy he’d heard, whoever he was. Hill Holliday got the Wang account.

That led to other major accounts: Nissan, Bank of Boston, John Hancock. By the time Interpublic bought Hill Holliday in 1998, Connors was overseeing a staff of 600 in four cities — New York, Fort Lauderdale, Framingham, and Boston — with company billings reported at $600 million annually.

And then Connors did something to make even more money.

In 1995 Connors got a call from a Dr. Jean Mooney, who years earlier had helped one of Connors’s sons with a learning disability. Mooney called Connors that day about her own son, John. His company, which put on medical trade shows, had relocated to Hartford, but he hadn’t wanted to leave Boston. His mother asked if Connors would meet with John and maybe help him find a job. Connors reminded her that he worked in advertising. She said he was the only one she knew to call.

A few days later, John Mooney met with Connors in his office. Mooney described how his client work included the American Medical Association and its annual conference in Chicago, for which doctors flew in as a requirement for reaccreditation. As an aside, Mooney said it would be smart if somebody created a traveling medical trade show; you could go to the doctors instead of them coming to you. Connors stopped him short. He asked why he and Mooney couldn’t do that.

Mooney balked. “I can’t start a company. I’m only 32.”

Connors laughed. “I started this when I was 25.”

The two left the meeting that day with Mooney saying he’d have to consider his options. Six months later, Connors got a call from Mooney. He asked if Connors was still interested. “Of course,” Connors said.

Connors fronted a couple million to create a company called M/C Communications. Mooney parked his trade show in various cities. Connors, who by this time was the chairman of Partners HealthCare, convinced Harvard Medical School it could earn more money by sending its professors to the trade shows, which heightened the shows’ appeal. The firm’s sales force then asked pharmaceutical and medical device companies to display their wares at the shows, for a substantial fee. By 2004 M/C Communications had shows in 77 cities. That’s when the Boston-based equity group Bain Capital got involved. That year, it acquired M/C Communications for an undisclosed sum, though it’s been reported at around $450 million, a figure that Connors himself does not dispute. “For John, and for me, it was the biggest payday ever,” he says.

M/C offers an example of Connors’s business acumen — but it also shows how entangled his interests have become. Connors sold M/C while serving as chairman at Partners. Yet he never directly disclosed his stake in M/C to the Partners board, even though his company had relationships with numerous Harvard Medical School professors — professors that are affiliated with Partners’ hospitals.

Last year, the Globe ran a story saying that Connors had failed to disclose this potential conflict of interest. That story, however, only compounded how intertwined Connors’s business interests had become. The piece appeared at the same time Connors was attempting to buy the Globe.

Three-time Pulitzer Prize winner Steve Kurkjian had spent about six months reporting the story, part of a larger series called “The Partners Effect,” which examined the effect of the state’s largest healthcare provider on the rates everyday families paid for medical insurance in Massachusetts. The Globe’s Spotlight Team began publishing stories on Partners in late 2008, and continued through the spring of 2009. By the time Kurkjian’s story on Connors and M/C Communications ran, on May 31, 2009, the Globe itself was facing closure. The New York Times Company, the Globe’s owner, had threatened to shut down the paper unless its unions agreed to a series of cuts in pay and benefits. In the midst of this threat, potential bidders began speaking to the paper. Connors was one of them. In other words, he wanted to buy the paper at the very time it was investigating him — for an alleged conflict of interest.

All of this had a curious effect on Kurkjian’s piece. The tenor was so careful that it muddied the story’s point. It takes a couple of reads to figure out that Connors probably should have told the other Partners trustees about his stake in M/C Communications. “That story kind of landed like a thud,” says one person who worked on the series for the Globe. (Connors said in the piece that he told Partners executives about M/C, who thought he didn’t need to disclose it to the board.)

The other strange thing about the article was its placement. One of the most powerful men in town chairing arguably the most influential board in the state had failed to report his interest in a $450 million sale — and the story runs inside the paper? “I heard thirdhand that Jack felt that he had won on that one, that he had worked us over,” says another person assigned to the series. “I didn’t think that was the case.”

Connors himself won’t comment on the piece. About his alleged conflict of interest, he says he disclosed everything he needed to disclose to the Partners board. Globe editor Marty Baron won’t comment on the story, either. But another person at the paper that was close to the Partners series says, “It was such a terrible spring last year…. We were in a crisis. We weren’t going to beat the hell out of someone who might save us.”

“Just so you know, this entire morning will be scripted,” Connors says, half smiling. We’re standing outside St. Mary’s Chapel at BC on a dewy Tuesday morning in June. We’ve just left Mass — Connors goes about five times a week — and he wants to show me what he does these days, now that he’s made two fortunes and doesn’t see the point in a proper Jack Attack. We get in his black Lexus and head to Dorchester.

A few years ago, he got a call from Boston Mayor Tom Menino. The mayor described how inner-city 11- to 14-year-olds “were too old to be young and too young to be old,” and therefore at risk of violence. To keep these kids out of trouble, Connors and Menino built a summer camp on Long Island, off Quincy. Fifty percent of the kids had never swum in the ocean before, even though they lived three miles from it. Camp Harbor View just completed its fourth season. Enrollment has increased every year. Full-time staffers check up on the kids throughout the year. Some former campers are now counselors-in-training. It’s all thanks to Connors, who has raised $25 million thus far. The camp has exceeded even the mayor’s ambitions. As Menino would later say, “When Jack does anything, he does it all the way.”

This morning’s trip is to Pope John Paul II Catholic Academy. The car ride, these post–Hill Holliday years — they’re really about Connors’s legacy. When Connors discusses that topic, which isn’t often, he’s cryptic. He’s savvy enough to know that saying “my legacy” is counter-productive to the very pursuits you secretly want the legacy to comprise; it also makes you sound like an ass. When he talks about it at all, he sounds like a politician. He says he doesn’t care what people think of Hill Holliday. He wants to be remembered for coming here — to Roxbury, Mattapan, Dorchester, the places where “there’s nobody else standing in line to help” — and giving away his money.

When then-Archbishop Seán O’Malley approached Connors about the project that would ultimately become Pope John Paul II, Connors wasn’t exactly a beloved figure within the Church. A few years prior, Cardinal Bernard Law had called Connors on a Friday to tell him that the Globe was about to go with a story for that Sunday’s paper that said certain priests in the archdiocese had sexually molested minors. Law wanted Connors’s advice. Should he talk to the paper? Connors asked how many cases there were. Law said one or two. In that case, Connors said, he could wait until Monday to respond.

Of course, it wasn’t one or two cases. And as the sex abuse scandal unfolded, it became international news. Roughly a month later, Law called Connors again, asking if he should respond to queries from the New York Times. This time, Connors told Law he couldn’t offer any advice. “You lied to me.”

From that point on, Connors became one of Law’s most vociferous critics, even asking for his resignation. Leaders within the archdiocese remembered that. And so when O’Malley came to Connors for help in rebuilding Catholic schools, Connors said he’d do it, on one condition: He wanted to use his ideas, not the Church’s. “Because I have never volunteered for something where people hated me,” he says as he drives through Jamaica Plain.

Five years later, the approach of pooling parishes’ resources into one neighborhood academy has earned raves from O’Malley. “Jack is an example of discipleship in action,” O’Malley says. The academies were built in some of the state’s poorest areas — Brockton, Mattapan, and Dorchester — because, as Connors says, “If we fail these kids, then the [parish] closings are going to accelerate.” There are now four academies, and Connors, a year after the $2 million gift from Ted Kelly and Joe Tucci, has raised close to $60 million.

Driving on Columbia Road now, we see the school. It’s red brick, three stories, built in 1909. Around us are three-decker homes, some with gated windows. Connors pulls into the narrow parking lot and finds the one available spot, directly in front of the school. “Look at this, the luck of the Irish.”

He heads out and strides to the front door. But it’s locked. Connors doesn’t have a key.

“That wasn’t part of the script,” I say.

Connors looks up at the sky, and then mock yells, “We rehearsed it!” We begin walking away, looking for a side entrance, when suddenly the door swings open. Someone had noticed it was Connors at the door and rushed to let him in.

With Connors, it still happens that way.

First published in the print edition of the October 2o10 issue.