Shirley Leung

Who is Jack Connors backing in the governor’s race?

In this gubernatorial race, will Jack Connors swing Republican?

That’s the buzz around town about the Boston powerbroker who has been a big giver to Democrats over the years.

Connors supported Deval Patrick in the last election, but hasn’t said whom he will back this time. If a Republican wants to take the corner office, he will need influential Democrats such as Connors.


Connors, the retired chairman of advertising giant Hill Holliday, is remaining mum. He supported a Republican before — Mitt Romney in 2002. (His last donation to a gubernatorial candidate was to Steve Grossman last summer, before the Democrat had announced.)

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Connors ducked my calls on this topic — a rarity for someone who loves to gab to the media. Well, it is high vacation season, and he was in Maine last week, but I’m pretty sure they have cellphones up there. Perhaps he was too busy hanging out with the Bushes?

The whispers about Connors’s political allegiance amped up earlier this month when John Connors, Jack’s son, told the Globe he’s backing Republican Charlie Baker. Does that mean the old man isn’t far behind, or, is his son doing his bidding?

More fuel for the fire: a $1,000 donation to the Massachusetts Republican State Committee from a John Connors of Hill Holliday, according to the latest campaign donation reports.

The younger John Connors explained to me that the $1,000 check is from him. There’s reason for some confusion: he doesn’t work at Hill Holliday any more, but rather runs his own advertising agency in Waltham, Boathouse Group. Yet somehow the GOP listed his employer as Hill Holliday, his father’s old firm.


So what is dad up to?

“I have no idea what he is doing,” said the younger Connors, who was kind enough to phone in from his vacation in Ireland.

Connors, who is 47, knows Baker through his wife, Lauren Baker, who was John’s boss two decades ago at Hill Holliday. Lauren worked for John’s father until 1999; the younger Connors left Hill shortly afterward.

The son has donated mostly to Democrats, so when he started to raising money for Baker this summer, people kept saying: “Have you asked your dad about that?”

He thought it wise to debrief him.


“ ‘You gotta to do what you believe in,’ ” Connors recalled his dad saying to him, but not without a tongue-in-cheek warning: “ ‘You are out of the inheritance.’ ”

John Connors told me he believes Baker can bring prosperity to all of Massachusetts, not just Greater Boston. And in our polarized political world, Connors doesn’t want to vote based on whether a candidate bleeds red or blue.

“It’s become much more about the person than the party,” said Connors, who has raised more than $20,000 for the Republican.

His father and Charlie Baker have known each other for two decades — again thanks to Lauren. I can see the two bonding over healthcare issues — Baker, former CEO of Harvard Pilgrim and Connors, chairman emeritus of Partners HealthCare, the goliath hospital system.

Baker told me his conversations with the senior Connors always begin and end this way: “Please say hi to your wife.”

While the candidate himself thinks of Connors as a friend, he doesn’t believe the business leader is ready to declare a favorite.

“I don’t think he’s made any decision,” Baker told me recently, as he and Lauren greeted potential voters at a festival in Quincy.

One person who has made up her mind is Connors protege Karen Kaplan, Hill Holliday’s current CEO and chairman. She backed Baker in his losing bid against Patrick in 2010. Kaplan has known Baker for 30 years, and their children practically grew up together on the North Shore, including dinners together on Sundays.

“For me, I think he’s a remarkably balanced and prepared candidate,” said Kaplan. “I do think the business community is pretty excited about him.”

Whether Jack Connors will go public with his choice likely depends on what happens with Partners’ efforts to add three hospitals, including South Shore, to its already bulging portfolio. Attorney General Martha Coakley, herself a candidate for governor, has given her blessing to the takeovers — with some restrictions — but critics are trying to block the deal, arguing the hospital chain will still be too powerful.

A judge will review the settlement in late September, after the gubernatorial primary. If the case drags on and Baker faces Coakley in the general, the timing could put Connors in a tough spot to fly the GOP flag.

Shirley Leung is a Globe columnist. She can be reached at Follow her on Twitter @leung.