The Invisible Hand of Jack

He has worked this town for the last 40 years, from healthcare to the church to big business. Now, in retirement, he's building a camp for kids and showing Boston's power brokers how to lead with their hearts - and their wallets.

(Photo by Tanit Sakakini)
By Steve Bailey
June 3, 2007

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Jack Connors and I are sitting on our usual bench at Castle Island. Lunch is the usual, too: couple of hot dogs each, mustard and relish, and we split an order of onion rings, though neither of us needs them. We talk about the governor’s race. We gossip about what’s happening downtown and at the Globe. We talk about how he feels about retiring from the ad agency he spent a career building.

We’ve shared this bench for years now. But I’m not so naive as to think I’m the only one Connors brings here. He has been coming here for decades, starting with the great Globe editor Tom Winship and former Globe president John Giuggio just after he won the newspaper’s ad business. Partners HealthCare chief executive Jim Mongan has eaten hot dogs at Sullivan’s, as has political strategist John Sasso and many more. But who really knows but Connors? And he’s not telling.

It’s a warm, lazy day, and the place is alive with moms and their strollers, old folks in their folding chairs, and dogs out walking their owners. As we finish our hot dogs and start walking, I’m telling him about my weekend trip to Georges Island with my wife, Beatrice, and our little one, Mona Lee. In all my years in Boston, it was my first time to Georges Island, and it was fabulous. Just imagine what it could be if some rich guy would put a camp out there for kids, with sailing, camping, the works. You know any rich guys, Jack?

In 10 minutes we are in his car, barreling toward another of the Harbor Islands. Connors is telling me about his vision to build a summer camp – not on Georges Island, but on the end of Long Island, for hundreds of kids from Boston. Load them all on school buses in the morning. Bring them out here to this perfect spot he has found on the harbor. Run them ragged all day and then take them back home on those same buses. What he lacks in detail, he makes up for in enthusiasm. It’s an idea drawn in equal parts from his boyhood days at summer camp a half century ago and what he’s been reading every day about the epidemic of killing in the city’s neighborhoods. Ten million is what it will take, he figures. He’ll put up the first $2 million, then find a bunch of rich pals to pony up the rest. It won’t take long, he says. No problem.

As we cross the rickety old bridge to Long Island, a place inhabited by hundreds of homeless men and women bused from the city every afternoon, we have to figure out how to get past the security checkpoint just on the other side of the bridge.

“I could tell them I’m from the Globe,” I offer.

“Geez, don’t do that,” Connors winces.

I should have known better. The guy sitting beside me is a born salesman, and it took but a minute of a little Irish cock-and-bull story and we are on our way. He is laughing out loud. This guy, a legendary Boston power broker worth hundreds of millions, this guy whose expletive-laced rages – Jack Attacks – once landed him on Fortune magazine’s list of toughest bosses in America, is having a blast as he nudges his black Mercedes through the trees and down the narrow winding road. And, suddenly, we’re there: Welcome to Jack’s Camp.

Or at least Jack’s Camp in Connors’s mind. Where the rest of us would see a huge empty field with a spectacular view of Boston’s skyline across the harbor, Connors sees kids playing baseball and basketball, doing arts projects, and eating lunch. He climbs the huge boulders to show me where the kids will swim. Where I see a rocky beach, he sees potential. I talk about the problems; he talks about the chance to make a difference. “Just imagine,” he says. “Just imagine.” And so I do.

On the way out, we have one stop to make. At the administration office of the homeless shelter, Connors hunts down someone – anyone – who will accept a donation. First upstairs and then down to the basement; no one seems to know what to make of this insistent guy in a suit trying to shove a $100 bill into someone’s hand. But Connors won’t leave until someone takes it. After all, this good Catholic boy has to atone for that fib he told to get us past the security guard an hour before. A small price to pay for forgiveness.

Jack Connors is the last man standing. For decades, he has been the face of corporate leadership in this town, an often derided but increasingly rare commodity as Boston has seen one home-grown company after another turned into a branch office for some national or global behemoth. His influence has been predicated not on running the biggest company in town – his Hill, Holliday, Connors, Cosmopulos wasn’t even the biggest ad shop in Boston when he sold out to one of those global giants – but a network of relationships unparalleled in Boston. That network has made a poor boy from Roslindale a fabulously rich and powerful figure. But it has also given him the chance – the obligation, he would say – to give back.

Most of Connors’s generation of business leaders have retired and moved off the public stage. Bankers Terry Murray and Chad Gifford and former John Hancock boss David D’Alessandro, to name three, sold their companies and have largely faded away. But Connors has no intention of following them. Since officially retiring as chairman of Hill Holliday at the end of last year, he has literally stepped up, not down: He moved his office from the Hancock Tower’s 39th floor, where he had held court for 27 years, to the 60th floor, atop Boston’s tallest building – a building now dominated by the new masters of the financial universe, private equity managers. Hill Holliday itself may be willing to move from Boston’s symbolic center of gravity for cheaper digs elsewhere, but not Connors. The message is unmistakable: I’m not going anywhere.

Connors has a clear and ambitious vision of what he wants to accomplish in his new life. Put simply and without apology: He wants to set an example for corporate Boston, his peers and those who follow, that their responsibility extends beyond the bottom line. Connors, who at 64 goes to church nearly every day, takes his inspiration from the Book of Luke. “ ‘To whom much is given, much is required,’ ” he says. “That is all that is going on here.”

“I am not selfless,” says Connors, who splits his time among Boston, Florida, Cape Cod, and Vermont. “I have fancy houses. I am not giving it all away. Shrouds don’t have pockets, though some guys think they do.”

Post-Hill Holliday, Connors remains a man with his hand still firmly on the levers of power that will be key in executing the job ahead. He is chairman of Partners HealthCare, the 800-pound gorilla of the state’s hospital industry. He has taken on the job of remaking the parochial schools for the Archdiocese of Boston. He is chairman of the Board of Fellows at Harvard Medical School. The only person to ever twice be chairman of the board at Boston College, his alma mater, Connors is no longer on the board because of term limits, but his influence is undiminished. Connors, the businessman, started, built, and sold not one but two companies for fortunes and has now launched yet another healthcare company. He tried and failed (for now) to buy this newspaper from the New York Times Co. He sits on a fortune estimated at $500 million and gives away millions a year through the Connors family office. And in his spare time, he is getting his camp for inner-city kids up and running in time for summer.

What has not changed is what has always been at the core of the often invisible hand of Jack Connors: the remarkable network of relationships. Think of it as a competitive advantage built over 40 years of working the town, making or receiving 80 to 100 calls a day, doing favors, little and big, for people big and small. The call volume is down to maybe 50 a day, says longtime assistant Julie Joyce. But now the calls aren’t about nailing down some advertising account. They’re about getting a summer camp built, a grammar school rebuilt, or a friend’s son into BC.

You tell me: Who is going to say no when Jack comes calling?

Connors’s plate is overflowing in this, the second season of his life. Apart from his family and Hill Holliday, Connors has no greater passion than Partners HealthCare. The 1994 combination of Massachusetts General Hospital and Brigham and Women’s Hospital is widely considered the most successful of the big academic hospital mergers around the country. Having Connors looking over Partners as chairman for the last dozen years has not hurt. Critics of Partners believe its growth is driving up healthcare costs and squeezing smaller competitors, particularly the community hospitals. Connors isn’t buying it. “It is the best thing I have ever done aside from raising a family,” he says. “To be a member of a team that has taken the hospitals in this state from shutting down hospitals and losing a lot of money to the point where they are the heartbeat of the economic engine of this state, it has been the ride of a lifetime.”

It even inspired him to build a new healthcare company. Dovetail Health in Needham is designed to provide a safety net for senior citizens living on their own by offering care at home. Run by chief executive Stever Aubrey, it is financed entirely by Connors. “I am investing in myself again,” he says. “When I look at my alleged success, the thing that I most made money on was myself.”

Connors is also digging in again at the Catholic Church after a very public falling out with Cardinal Bernard Law over the clergy abuse scandal. Connors was chosen by Cardinal Sean O’Malley to restructure the archdiocese’s school system and turn around its finances. The plan is to reverse years of declining enrollment by building new schools, refurbishing others, and putting the schools in the right places. “You have the coffee stores where there is no traffic,” says Connors. His first job is to raise $12 million for the rebuilding of two Brockton schools, a model for a new regional approach to Catholic education.

As if all of this were not enough to fill his retirement days, last year Connors and Jack Welch, the former chief executive of General Electric Co., joined forces to make a pitch to buy The Boston Globe from The New York Times Co. In typical Connors fashion, Welch got the headlines, but it was Connors who brought Welch into the deal, because, he says, he wanted to improve the paper. “Could it be better? It was better,” he says. “Circulation is down, so they cut back on the product. I have a counterintuitive notion. You invest in the product. You make the product better. I think it is disappointing that the Globe has been forced to cut back, cut back, cut back. That is not how you build. I didn’t build things by cutting back.” The deal has gone nowhere because the Times Co. has insisted it does not want to sell the Globe. Is it over? “When you are me,” Connors says, “you never say it is over. It is not over till we say it is over.” (When I asked him to respond to Connors’s comments, Globe publisher Steven Ainsley declined.)

In the meantime, when Connors is not taking in money, he’s giving it away – in piles. The Connors Family Foundation donates an estimated $7 million annually, the biggest gifts going to places closest to the family’s heart: Boston College, Mass. General, Brigham and Women’s, Harvard Medical School, and Connors’s favorite, the Mary Horrigan Connors Center for Women’s Health and Gender Biology at Brigham and Women’s, named for his mother and where his eight grandchildren were born.

His ambitions weren’t always so grand, not in 1970, when the next paycheck was not always a given. Connors was the president of a two-year-old ad shop on Newbury Street when he got a call from a sheriff’s deputy. The deputy didn’t know Connors but had heard he was a good guy and thought he would want to know that the sheriff’s office was about to padlock a Cambridge retailer by the name of National Sales. If those guys owe you any money, the deputy suggested, get it back today. Tomorrow will be too late.

In fact, National Sales owed Hill Holliday $20,000, a lot of dough in those days. The commissions in year one had totaled all of $37,000, and if the partners took home 80 bucks a week, it was a good week. Connors piled his partners, Steve Cosmopulos and Jay Hill, into Cosmopulos’s station wagon and headed to Cambridge. Connors’s advice to his partners: Let me do the talking.

He told the owner of the company, which sold everything from washers and dryers to stereos and cameras, they were in a pinch and needed to be paid. The guy, of course, told Connors he didn’t have the money. “Well, what can you let us have?” Connors asked. They settled on $4,000, but Connors wanted more. What about some TVs, some cameras? “I can’t let you do that,” the guy said. But Connors kept talking, and eventually they settled on one TV for each of them.

The boss directed them to the storeroom and signaled for the guard to let them in. “What did he say?” the guard asked Connors. Connors told him they were there to take some inventory to another store. Then the three ad guys started loading TVs, cameras, anything that would fit into Cosmopulos’s station wagon. When that car was full, Connors called his office and told someone to bring over Hill’s station wagon, which was parked in the alley out back. The keys were in the ignition, he said. The guy showed up shortly, but with a different car; he had taken the wrong one. No matter. They loaded it up and drove, slowly, back to Newbury Street. As they turned back into the alley behind their office, there was a guy in the street, furious because somebody had stolen his car. Connors again did the talking, trying to calm the guy down. I wasn’t trying to steal your car, Connors says. It was a mistake. He walked the guy around the car. Is your car OK? No need to call the cops, pal. Why don’t you just go in the back and pick out a color TV set? And so he did. And Connors and his partners took home the rest.

What Connors likes to call the “cowboys and Indians days” are gone if not forgotten. Connors and his three partners – Hill, Cosmopulos, and Alan Holliday – had all left the Boston office of the big New York firm BBDO Worldwide to strike out on their own. The idea was for each of them to put up $1,500 and be equal partners. The problem: Connors only had $500, but he got the other $1,000 from his dad, and he was in. Although he was considerably younger than the others, Connors got the title of president, he says, because he couldn’t write and couldn’t draw. They were the creative ones. He was the salesman, and the fancy title would help.

One of his first jobs was to go to the bank for a loan. How long was their $6,000 seed capital going to last, after all? Three banks and three rejections later, he needed to get smarter, so he did some research and found that a banker named Dick Driscoll at New England Merchants National Bank had gone to Boston College. He went into the bank’s Prudential branch and asked Driscoll for a $10,000 loan. Driscoll asked to see the company’s pro forma, or business plan. “What’s a pro forma?” Connors asked. But he got his loan, an early example of Connors understanding the value of networks, the BC network, in particular.

Connors & Co. weren’t exactly an overnight success. Ten years into the business, Connors, Hill, and Cosmopulos – Holliday left within a year – were still not making much more than $60,000 a year each. The break came when Connors got a call from the assistant of a top executive at Wang Laboratories, the hot mini-computer maker founded by Chinese immigrant An Wang. The executive, John Cunningham, had been impressed by a speech Connors gave at a career counseling seminar for BC alumni and asked if Connors was interested in competing for Wang’s advertising account.

Connors showed up at Cunningham’s Lowell office, but Cunningham immediately realized it was not the same guy he had heard speak. Cunningham’s assistant had called the wrong guy. Connors hadn’t spoken at the career seminar at all, but he made his pitch anyway. So Cunningham heard out the guy from BC – a guy, who, what do you know, is also Irish Catholic and turns out to have grown up just a mile and a half from Cunningham – and ultimately hired him. The way Cunningham saw it, Wang’s gang of friends were mainly Chinese, they played mah-jongg and tennis, and Cunningham didn’t play either. Maybe it was time for him to build his own gang, starting with this sharp Irish ad guy from BC. Hill Holliday was on its way.

Over the next two decades, Jack Connors at Hill Holliday and Ed Eskandarian at Arnold Worldwide came to dominate the Boston ad scene. Hill Holliday’s clients included Anheuser-Busch, Dunkin’ Donuts, Liberty Mutual, AOL, Novartis, CVS, and Verizon Wireless. In 1998, Connors sold Hill Holliday to Interpublic Group for more than $115 million, with the Connors family share somewhere north of $100 million. He continued to run the agency, gradually turning over responsibility to his handpicked management team, headed by chief executive Mike Sheehan.

“I’m in the relationship business, no question,” says Connors. “There were years when the creative was great, and there were years when the creative sucked. My job was to keep the client through all of those years.”

If his sale of Hill Holliday made Connors rich, his sale of M/C Communications made him far richer. In 1994, Connors had hired a fellow BC alumnus named John Mooney, who had this big idea. Mooney’s idea was a medical trade show for doctors, to provide continuing education for primary care physicians and marketing opportunities for managed care companies. When Connors sold Hill Holliday to Interpublic, he bought back M/C Communications himself for $12 million. In 2004, Connors and Mooney sold the trade show company to Bain Capital for $450 million. Connors’s share: $250 million, more than twice what he made on Hill Holliday in 30 years. “How silly is that?” asks Connors.

An old Jack Connors maxim is you make money with friends, not enemies. You get things done in town with friends, not enemies. “I never made any dough hating anyone or being arrogant,” he says. “People vote for things they like, and they voted for me a lot because I was sort of easy to like. I get along with a lot of people.”

But not always. Consider the never-before-told stories of Anne Finucane and David D’Alessandro, two of Connors’s closest friends in Boston.

Finucane is the Northeast president and chief marketing officer for Bank of America, making her one of the most powerful women in the business community here. Like so many, she got her start with Connors and in 14 years rose to executive vice president. But it ended badly. In 1994, Finucane became the target of a classic “Jack Attack” in front of some other executives, and she left a few months later. She eventually went to work for Terry Murray at Fleet Financial, running the advertising and marketing side of the business. And guess who landed the ad account?

This year, Hill Holliday won a big piece of the Bank of America account, a huge achievement for a Boston ad agency. And if you ask Finucane, she lists Connors, Murray, and Gifford as her mentors. Connors “hasn’t been successful by making enemies. That is his big thing,” Finucane says. “With some distance, he still had the best agency in town. When I left, he was my first client. We are very good friends.”

The falling out between D’Alessandro and Connors was more painful – and less easy to repair. There were no two closer CEOs in Boston than these two. When D’Alessandro came to Boston as head of marketing and communications for John Hancock, he talked with Connors about how to navigate the business culture and eventually gave his ad business to Connors. Hill Holliday produced a landmark ad campaign called “Real Life, Real Answers” that boosted the already soaring profiles of both Hancock and D’Alessandro. In addition to business, Connors and D’Alessandro shared a set of progressive political values and weren’t shy about pushing them. They endorsed higher taxes, stood up for striking janitors, and famously helped broker a deal for a new Fenway Park – though the Red Sox owners have since shown there is plenty of life left in the old one.

The friendship, however, nearly collapsed three years ago. Connors, the chairman of Partners HealthCare, had brought D’Alessandro onto the board. With the sale of John Hancock, D’Alessandro saw the chairmanship of Partners as a platform for continuing his civic role in town. He felt he had an agreement with Connors to be his successor, and twice passed up a chance to be chairman of Boston University in favor of the Partners job. Except it didn’t happen. Neither Connors nor D’Alessandro will talk about it, but other executives involved in the dispute say Partners chief executive Jim Mongan wasn’t comfortable with D’Alessandro as chairman, and it was left to Connors to relay the message. Others don’t think Connors wanted to step down anyway. D’Alessandro felt that if Connors were really his friend, he would quit the board. Connors didn’t quit, and the whole affair got personal and ugly. It took time, but today the two are friends again.

Like a lot of us, Connors is who he is because of where he came from. And more than most, he has never forgotten where he came from.

“I am a Boston guy. I am a homeboy,” he says. “I live less than 2 miles from the hospital where I was born. I live less than 4 miles from the house I was raised in. I live less than 10 miles from the high school I went to. I live 4 miles from the college I went to. I am a local.”

Connors was raised in a two-family house in Roslindale, and his family moved to Dedham when he was 11. His dad repaired heating and air-conditioning systems in big downtown buildings; his mom was a secretary. He worked his way through Boston College, hawking hot dogs at Fenway and driving a Checker Cab. “Peanuts! Hot Dogs! Ice cream!” Connors bellows, still the kid at Fenway all these years later. His hackney license – No. 5337 – sits on a bookshelf in his office as a reminder of his hack days. A taxi meter, a gift from D’Alessandro, sits nearby.

“I learned as much driving a taxi, selling hot dogs and scorecards as any academic experience I had,” he says.

Connors talks about the day that changed his life. He had started his career as a salesman for Campbell’s Soup Co., selling Swanson TV dinners and other frozen foods. This was 1964, and he was making $104 a week. His boss brought him in, told him he was doing a fine job, and gave him a $4 raise. “And there is plenty more where that came from,” the boss told him. Time to move on, Connors thought.

The next stop was BBDO, one of the largest ad agencies in the country, where Connors was the junior member on the agency’s largest account, the Dodge car and truck account. After two years working in New York, he was summoned to a meeting in Detroit, where his boss announced that Connors, one of the company’s youngest executives, was being promoted to run the client’s largest region. “It was the next phrase that literally changed my life,” says Connors: “ ‘And if he keeps his nose clean, he will be a vice president in Detroit by 30.’ . . . In other words, if I worked my ass off, the brass ring was a life sentence in Detroit.” The next day, Connors quit. He and his wife, Eileen, who was pregnant with their first child, made Boston their permanent home.

And why not. Connors has prospered here beyond anything he imagined. He talks about his mother, “a real force in my life,” who died when he was a junior in college. She was a secretary for the chief executive of United Fruit Co., but she was fired when colon cancer made it too painful to go to work. “I contribute some of my success to being nice to the secretaries,” he says. He talks about his grandfather, a Boston cop, who was fired in 1919 when Calvin Coolidge, then Massachusetts governor, dismissed half of the city’s police force to break the police strike. When Connors was in the State House last year, helping to negotiate the state’s landmark healthcare bill, he refused to meet in the Coolidge Room of the Senate president’s office. He is not one who forgets.

“Stay humble. Don’t forget who you are,” he says. Says Connors’s son, John Connors III: “He knows he has been lucky. He knows it could have dropped the other way.”

It is those values that Connors has carried with him all these years. And now he wants to impart them to others.

“I enjoy giving help,” he says. “It was truly a lot of fun making money. It was a hoot, dodging bullets and pulling a deal off and beating guys to the punch. It became sort of a sport. You know, I was a terrible athlete. With this, I became sort of a silver medalist in my sport. It is more fun giving it away.” He adds: “There are seasons in people’s lives. One of my seasons, a very long season, was making money. The second season is giving it away.”

Which takes us back to Jack’s Camp.

The plans were first confirmed in February by Mayor Tom Menino, with Connors, as usual, well in the background. Scheduled to open in July, the camp this summer will offer 600 inner-city kids, ages 11 to 14, everything from ball fields to a beach to lessons in the performing arts.

But weeks before news of the camp broke, Connors was working his network. On a frigid morning in January, Connors picked up House Speaker Sal DiMasi at the State House. He wouldn’t tell him where they were going. On the way, Connors told DiMasi about his vision for a summer camp. By now, the Irish guy in the black Mercedes was a familiar figure at the security checkpoint just across the Long Island bridge. It was 11 degrees, and the wind was howling off the harbor when Connors dragged DiMasi out to the rocky water’s edge to explain he needed a guy with a barge to haul in tons of sand to make a beach. And, by the way, Connors said, I don’t want to pay for it.

“If you let me get back in your car,” the speaker pleaded, “I’ll do anything you want.”

Who, after all, is going to say no to Jack Connors?