Bob Baker

An hour of banter, laced with laughs in March of ’71 and pals-for-life was a given. The occasion was the Ad Club of Boston’s lunch for newly elected members of the board of directors. Jack Connors was founder of up-and-coming ad agency Hill Holliday Connors Cosmopulos; I at the time was creative director of K&E–Boston.

Jack, who passed away on July 23, was a certifiable force of nature, an iconic figure of such relevance in the advertising world and as an institutional influencer and philanthropist that a 2010 Boston Magazine cover story on him was titled “The Last King of Boston.” The Boston Herald called him “Soul of the City;” Cardinal Sean O’Malley said, “He wasn’t a celebrity, he was a hero.”

Our shared sense of humor and what I call “sense of human” only strengthened the bond when I made a move that defied conventional wisdom, but appealed to the love of “boldness” in Jack. After 10 years of award-winning success on the Boston ad scene, I decided to “quit working the job of life and begin playing the game of life” (my mantra of sorts). In 1974, I set up my creative shop in a place called Freedom… a.k.a. Marblehead.

From there on out, our friendship flourished in so many fun ways — unfortunately space allows only a sampler of “touch points” here.

When I was creative director of K&E, I won Best of Show in New England’s top creative competition, the 1971 Hatch Awards, for my Vermont tourism campaign. Thus, when the trade press in 1975 announced that lowly one-man shop Baker Advertising in Marblehead had been appointed agency of record for Vermont tourism AND economic development, it was quite a coup. Just days later, a letter from Jack on HHCC stationery: “Nice going, you hot (bleep). I will now advise my financial managers to once again invest my millions in Vermont.”

One of the joys of being on my own is the freedom to explore ideas of all description. In 1980, I asked Jack if I could run my MagaBooks publishing idea by him. He invited me into his Hancock Tower office and I ran it by him. “Wow! How come nobody’s ever done that?! Let me give you my lawyer to help you protect it.” To my discredit, I never took him up on it.

1998 was a big story… in every sense. Jack sold Hill Holliday to Interpublic for very big bucks. A few days later, on the front page of the Boston Globe Business section, there was an unflattering photo of Jack Connors. I flipped a mental coin that said MYOFB on one side and “Warn your buddy!” on the other. I wrote Jack a letter something like: “Jack, I may infuriate you and lose our friendship, but I’ve gotta beg you to lose a ton of weight… and save your life! PLEASE!”

Four or five evenings later, the phone rings. “Bob, it’s Jack. I want to thank you, Bob. Only a true friend would take the risk of such loss to do the right thing.” That was a pivotal point in our friendship. Everything was good pals before then; now it took on an aspect of brotherliness.

Jack’s party celebrating his retirement from Hill Holliday, held at the Charles Hotel in Cambridge in 2006, was a master class in one of Jack’s Ten Commandments: Thoughtfulness. In addition to A-Listers aplenty among the 300 guests, there was a nice representation of people (like myself) you might not expect to see there. Dick Driscoll, the State Street Bank loan officer who had given Jack a startup loan for HHCC in 1968; Jack’s barber; the parking-lot attendant who gave him a rousing hello every morning. But the knockout… the heartwrencher… Jack’s co-greeter on entering the party, one of Jack’s closest longtime friends, former Mayor Kevin White… erect and immaculately presented in navy blue suit… but wan and barely audible, a captive of Alzheimer’s. Jack’s hand on Kevin’s shoulder welcoming and smiling proudly. A scene of soft radiance.

Jack would come visit me at my creative cave in Marblehead and we’d lunch at favorite restaurants the Three Cod in Marblehead or the Tides in Nahant. A sign of the extent he’d go to for a friend was when I was recovering from surgery at the Brudnick Center in Peabody in 2018. I checked my home phone voicemail and there was a message from Jack’s office saying he was en route to Marblehead to see me! His office contacted him, and he went out of his way to come see me at Brudnick.

My emails to one of the 17 busiest people on planet Earth were always responded to the same day, or at the latest, next morning. And his responses were typically so generous: “Merry Christmas, Bob. You are such a gifted writer, and an even better friend.” His response to a nostalgia piece I wrote about the creative breakthrough of VW advertising and my fun involvement in it in the ‘60s: “Thanks for the walk down memory lane. You remain a gift to the English language. Love you. Jack”

The last email I got from Jack was his June 25 same-day response to mine asking if he’d pass a resume and cover letter from a daughter of a good friend of mine interested in medical research on to HR people he might know. “I’m off duty now till mid-July. But when I get back, I’ll jump on this and see what we can do.”

It’s a pretty long jump from Heaven, but if anybody can pull it off, it’s my pal Jack. Love ya, buddy.

Bob Baker has been an ad man for 60 years and a Marblehead resident for 59.