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Much of the establishment backed Charlie Baker during the pandemic. There has been one exception

Greater Boston Chamber surprised other business groups by repeatedly pressing Baker for more details on reopening

The Boston Chamber of Commerce and Jim Rooney, its chief executive, have publicly prodded the Baker administration to be more clear and forthcoming about the reopening process.
The Boston Chamber of Commerce and Jim Rooney, its chief executive, have publicly prodded the Baker administration to be more clear and forthcoming about the reopening process.Essdras M Suarez/ Globe Staff/file

During three months of a pandemic, much of the establishment has fallen in line behind Charlie Baker.

There has been one big exception: Jim Rooney and the Greater Boston Chamber of Commerce.

Over the past few weeks, the chamber and Rooney, its chief executive, have publicly prodded the Baker administration to be more clear and forthcoming about the reopening process, raising eyebrows in the city’s tight-knit business community that tends to work behind the scenes and air grievances privately.

Rooney’s criticisms have been constructive in tone, devoid of the negative or personal attacks that are now so common across the country. But they still stand out as one of the few points of rebuttal to a governor with soaring popularity, especially in how he has handled the COVID-19 public health crisis.

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Rooney’s forward approach casts a light on a relationship with Baker that goes back more than four decades, to the dorms of Harvard University, and up through the ranks of government and corporate life to the peak of power in Massachusetts.

Since becoming the chief executive of the Greater Boston Chamber of Commerce in 2015, Rooney has been unafraid to challenge Baker in public — pushing for an increase in the gas tax, for example, last year. Still, Rooney, who was in Harvard’s Class of 1979 with Baker, calls the governor a “longtime friend.”

Rooney said the issues that the chamber has raised about Baker’s plan to reopen the economy reflect the concerns of his members. Unlike some restaurateurs and small business owners, the chamber is not pushing Baker to reopen the economy at a faster pace; rather Rooney has hammered away at the need for more clarity around child care and public transit options that will enable more people to return to work when the time is right.

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“I hear what is on their minds. Hopefully this is valuable information,” Rooney said, adding that others "may think ‘Oh, Jim and Charlie are fighting.’ We’re not.”

Does Rooney get under Baker’s skin? No one who knows both would talk publicly about this.

However, Baker has talked directly with many leaders during the reopening planning but not Rooney.

The governor declined an interview to discuss his relationship with Rooney but issued a statement through a spokesperson that reflects his typically restrained public remarks: “Governor Baker has known Jim professionally for many years and appreciates the Boston Chamber’s viewpoint as the administration always works to hear from a variety of stakeholders.”

Since the chamber’s disapproval, others have also begun to call out Baker. In separate appeals, Congresswoman Ayanna Pressley in a series of tweets and a group of rank-and-file Beacon Hill legislators led by Cambridge Representative Mike Connolly urged the governor to delay the reopening because the virus isn’t under control.

Meanwhile, Jon Hurst, president of the Retailers Association of Massachusetts, has repeatedly criticized the administration for restricting mom-and-pop shops. Unlike many of the big companies in the chamber, small retailers can’t really work from home. Hurst’s organization also doesn’t have the same clout on Beacon Hill as the chamber, nor the roster of marquee names that form the core of Boston’s business community.

Those who know both Baker and Rooney insist there is no rift.

“They think highly of each other and they respect each other,” said Tom Glynn, who ran the Massachusetts Port Authority under Baker’s first term and was Rooney’s boss when they worked together at the Massachusetts Bay Transportation Authority. “They each have too much integrity to let friendship get in the way of their responsibilities.”

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Hill Holliday CEO Karen Kaplan, who co-chaired the chamber’s search committee that selected Rooney for the top job and is a longtime friend of Baker and his wife, Lauren, said the governor welcomes different points of view.

“Charlie likes input,” said Kaplan. “Jim has a point of view, and he likes to share it. … I don’t see that as a negative. I don’t think Charlie sees it as a negative, either.”

Tom Finneran, the former House speaker who has known both Rooney and Baker for a long time, said the two have “more in common than there is in conflict."

“If there is any friction whatsoever, they are CEOs with two different constituencies," added Finneran. "It would be insane to think they would sing together like they’re in a choir.”

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In the 1990s, Baker was a rising star on Beacon Hill, moving up the ranks to become health and human services secretary for Governor Bill Weld and later serving as his administration and finance secretary, as well as for Governor Paul Cellucci.

While at Harvard, Rooney logged nights as a track laborer at the MBTA, and after graduation went to work for the agency. He rose to run the T briefly as its acting general manager before becoming a top administrator at the Central Artery Project, starting in 1994 and then at the Massachusetts Turnpike Authority.

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By the mid-1990s, the costs of the Central Artery Project — a.k.a. the Big Dig — had escalated significantly. It was up to Baker and Rooney, among others, to figure out how to pay for it all, while not starving other highway work around the state.

For the next three years, the two met frequently and traveled to Wall Street and Washington to meet with rating agencies, investment banks, federal highway officials, and members of Congress.

Their task was made all that more difficult because of the directive from two successive Republican governors: no new taxes.

Eventually, they hammered out legislation in 1997 that would, among other measures, use revenue from tolls within Route 128 to help pay for the extra costs.

“Both are talented, smart, and focused on the task, both then and today,” said Joe Sullivan, lead negotiator for the House of Representatives during those talks. “Their ability to work together at that time, during that challenge, was something that benefited our state and allowed us to finish the plan that ultimately finished the project.”

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Rooney’s and Baker’s paths would intersect publicly again in 2015. Baker had just become governor, while Rooney had been the longtime chief of the Massachusetts Convention Center Authority and was pushing for a $1 billion expansion of the South Boston convention center.

Baker, who had been lukewarm about a bigger center, held off issuing the bonds to finance the project. The expansion was Rooney’s baby, but by that March, he was offered the position at the chamber. During the interview process, Rooney had sought out Baker’s opinion, and wanted to gauge how they would work together if he became the chamber CEO.

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“He encouraged me to do it,” recalled Rooney.

One month after Rooney took the chamber position, Baker shelved the Southie center expansion, citing the $1 billion expense. Some observing the process at the time theorized that Baker would have been more open to the project had Rooney remained in charge.

“If Rooney had stayed at the convention center, Charlie would have been much more sympathetic to the expansion,” said Glynn, the former Massport CEO.

Some in the business community privately suggested Baker’s decision to put the expansion in limbo is a factor in Rooney’s rather blunt tactics with the administration.

Rooney said there’s absolutely no connection. That was a previous job, a prior career.

“It’s history," he said.

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Rooney took over the chamber when it was at a crossroads.

His predecessor, Paul Guzzi, was the consummate Boston insider, a conciliator who preferred to influence policymakers behind the scenes during his 19-year tenure. When the chamber board hired Rooney, he pledged to remake the chamber to reflect the changing Boston business scene. He courted millennials who wouldn’t normally attend the suit-and-tie breakfasts that are the chamber’s stock-in-trade, and made the group more welcoming to women and people of color.

“When he came in, he was able to see the future of the chamber had to be different,"said Gloria Larson, the former president of Bentley University who sits on the chamber board and worked with Rooney when she chaired the convention center authority board.

On occasion, the Rooney-led chamber staked out positions that differed from those held by other business groups, or Baker. The roughly 1,300-member chamber was an early supporter of a bill that would allow transgender people to use the bathroom for the gender with which they identify, for example, and also of legislation aimed at encouraging pay equity for women.

Then there was the transportation debate last year, when the chamber and the administration were at odds, as Rooney tried to corral a diverse range of business interests behind new sources of revenue to improve the state’s public transit and roads.

The toughest part? Reaching consensus on the gas tax. Some prominent groups, including Associated Industries of Massachusetts and the Mass. High Technology Council, said they saw no need to raise the gas tax, essentially siding with Baker, who was pursuing a different approach with neighboring states that would funnel fuel surcharges to transportation projects. The House ended up supporting a 5-cent gas tax hike in March; the issue is now before the Senate.

At AIM, chief executive John Regan said he has found, over time, that working behind the scenes is more effective: “We try as often as we can to be extremely collaborative, to try to figure out how and where people are coming from and make the best case that we can on behalf of our members. All of that is behind closed doors and privately, not to back anybody into any corners.”

Case in point: During the COVID-19 pandemic, business groups aired concerns to Baker’s economic development secretary, Mike Kennealy, on his frequent conference calls, and in private meetings with a Baker-appointed reopening advisory board. But few would take on the governor publicly during the past three months.

Rooney and the chamber took many other business groups by surprise in early May when they issued two policy briefs that challenged the governor to provide more information on his reopening plan — both within two weeks of Baker’s target date for reopening. In particular, Rooney wanted more details on virus and antibody testing, child care, and transportation.

“Just telling people you’re doing a good job and supporting whatever they say, I don’t think it’s helpful,” Rooney said. “I try to do it without taking trivial shots."

But the chamber was conspicuously absent from a recent administration press release extolling several business groups and their members about work-from-home policies. Rooney explained he didn’t respond in time to participate.

The chairman of the chamber’s board, Paul Ayoub, a real estate lawyer at Nutter McClennen & Fish, said Rooney’s approach to the pandemic is no different from a number of issues the group has tackled.

“The chamber doesn’t ask everyone to agree with us,” said Ayoub. “The most important thing is to have different views come forth and from that gain a collective wisdom. ... What [we] are trying to do is what everyone is trying to do, and that is to find the best path forward for everybody involved. We are all in this together.”