With double duty, Phil Eng living out a leadership experiment

In the span of a few hours last week, Phil Eng switched roles in front of lawmakers without ever leaving the witness table.

When Eng began presenting on spending plans to the Joint Committee on Ways and Means at the University of Massachusetts Amherst, he was speaking as the state transportation secretary. An hour later, he picked up the microphone in his other capacity — general manager of the Massachusetts Bay Transportation Authority.

"Hello again, and good afternoon this time," he quipped before launching into testimony about the transit agency that serves eastern Massachusetts and whose service levels are a topic of constant debate.

"Last year, I came before you as general manager of the MBTA," he said. "And this year I have the privilege now, honor, of representing both MassDOT and the MBTA."

Eng, 64, is living out a leadership experiment at the state Department of Transportation: overseeing both the transit system and serving as the governor's statewide transportation point person. He has held both roles since October, when Gov. Maura Healey tapped him as interim secretary after a leadership shakeup.

At first, Healey framed the arrangement cautiously, saying she believed Eng was "capable of managing both" roles. Eng said his commitment to the responsibilities "is not going to waiver." But in recent public appearances — from the budget hearing to a speech before business leaders and a political breakfast in South Boston — the tone has shifted toward embracing potential advantages of the unusual structure.

That shift was on display Sunday at the annual St. Patrick's Day Breakfast, where Massachusetts leaders trade jokes and barbs. Healey was ribbed over turnover in her Cabinet, including multiple transportation secretaries during her first three years in office.

"So some of you may have heard from the press, there's been some little fodder about the turnover in our Cabinet lately," she said. "So look, I'm really excited to announce our new Cabinet, first delivered here this morning to you, all new members: 12 Phil Engs."

Behind her, a photo-shopped slide showed a dozen versions of Eng in different poses. It was the latest example of publicly celebrating a person who has earned the support of many lawmakers while also drawing hundreds of millions of dollars in support from the Legislature to boost the MBTA, its services and its workforce.

Jobs continue below the fold — post a job

Jim Rooney, who introduced Eng at a recent forum hosted by the Greater Boston Chamber of Commerce and once served as acting MBTA general manager himself, does not expect the arrangement will be long-term. Rooney is president of the chamber, whose business members rely on the T to get workers to their jobs.

"These are two of the most challenging jobs in state government," Rooney said. "All day long, you're dealing with issues that are being thrown at you, and there's so many dimensions to it."

Because of the demands of each job, Rooney said he doubts the dual structure will become permanent, predicting responsibilities would split again "sometime later this year" or early in the governor's second term, if Healey is reelected.

He added that although Eng has refused to accept the transportation secretary's salary — on top of the $586,000 he makes leading the T, the highest-paid state employee outside the UMass system — there could be "legal or ethical issues" with the arrangement long term.

Still, Rooney said Eng's experience across highways and transit makes him unusually suited to juggle the roles.

"Phil is an incredibly talented person who has the experience and background in all of the dimensions, whether it's transit or highway," Rooney said.

Join Senate President Spilka, Speaker Mariano, Senate Majority Leader Creem, Event Hosts Senator Payano, and Representatives Consalvo, Garballey, and Williams, other leaders of legislature, advocacy,and  medicine for Virtual 17th Annual Prostate Cancer Awareness Day, held on March 24th, 10 am to 2 pm. You will take part in expanding a Massachusetts model of national leadership in prostate cancer awareness, medical education, research and reducing health disparities. You will learn about the cutting-edge advances in prevention, diagnosis and treatment – and Prostate Cancer Resource Project, bringing the best available quality care to Massachusetts men and supporting them every step of their medical journey. This event is organized by AdMeTech Foundation, in cooperation with the Prostate Cancer Action Council.

Eng has framed the dual role as a continuation of the career path that shaped him.

Speaking to business leaders earlier this month, he described a 40-year career in public transportation that began as a young engineer in New York City. Early in his career, he said, he was responsible for inspections across more than 2,000 bridges, including the East River crossings.

"I had a chance firsthand to see not only what that does when you don't invest in your infrastructure," Eng said, recalling the maintenance gaps he encountered, "but really watching the leadership… how do you take those inspection findings and evaluate them properly, and then how do you actually keep hundreds of thousands of vehicles and trucks and people moving and still fix the system?"

Eng moved through design, operations and maintenance roles before eventually serving as president of the Metropolitan Transportation Authority's Long Island Rail Road and interim president of New York City Transit.

That range of experience, he said, shaped his view that transportation decisions must balance the needs of both dense urban networks and smaller communities.

"You kind of have to really start to put it in perspective that every single thing we do is important to every single public that we serve," Eng said.

He also became accustomed to juggling overlapping responsibilities.

"For a period of time, I had three roles there," he said, adding that while working at the MTA he continued assisting the state transportation department build the Kosciuszko Bridge, connecting Brooklyn and Queens.

"So I've always been taking on extra roles," Eng said.

At Mass General Brigham, our leaders bring together the brightest minds to solve the toughest challenges in healthcare. From academic medical centers to community hospitals, mobile health centers and more we deliver compassionate, patient-centered care. The high quality care we provide is built on innovative research and visionary leadership throughout the system.

That experience shapes how Eng describes the advantages of leading both the MBTA and MassDOT.

One of the biggest barriers to progress, he said, is agencies operating independently even when they share the same mission.

"I've had the pleasure of learning over the course of time the importance of agencies working together and supporting one another," Eng said. "And then defining win-win solutions, versus saying 'I'm only worried about my own needs.'"

In an interview with the News Service in December, Eng said he is on the T, or some form of transit, nearly every day and regularly visits stations and work sites.

His commute often begins in East Boston, boarding the Blue Line and switching to the Green or Orange Line to reach the agency's downtown offices. Sometimes he takes the ferry.

Now leading MassDOT as well, Eng said he also wants to spend more time on the roads.

"A transportation network — it's not just the MBTA, it's not just MassDOT, it's the entire network," Eng said. "Because no matter where you live, you need to rely on those different modes."

Since moving from Long Island to the Bay State in 2023, Eng has pushed to change internal culture at the MBTA — encouraging employees to flag safety issues and accelerating infrastructure repairs.

"I don't want us to just do things the way we've done it," Eng said. "I really do want to think outside the box."

Money helps, and Eng's timing was perfect in that regard. A surtax on high earners approved by voters in 2022 has helped Beacon Hill dump significant amounts of new money into the T and transportation at large. 

Bill Bernadino, vice president of the Boston Carmen's Union Local 589, called Eng a "gift from God" during an event last year to mark the signing of a bill to protect transit workers from assaults.

Previously, employees had been reluctant to speak up about safety concerns, and departments often worked separately, said Caitlin Allen-Connelly, executive director of Transit Matters.

"He wasn't afraid to call people out and to really start to put forward a new culture where people felt empowered to talk about problems," Allen-Connelly said. "He's a very approachable person and culture change takes a while."

Legislative leaders said those changes have helped build trust.

"The Secretary has done a very good job of being visible, accountable, and straightforward with T riders and the public," said Transportation Committee Chair Rep. James Arciero.

Sen. Brendan Crighton, the Senate co-chair of the committee, said Eng's responsiveness has helped lawmakers track projects affecting their districts and constituents.

"He's one of the few people that will always pick up my call," Crighton said.

Rooney said Healey may be hoping Eng brings the same organizational changes to MassDOT.

"Systemic, organizational and bureaucratic and cultural practices and changes that he brought to the T that it seems as though he's trying to bring to the entire secretariat," he said, are a "good thing."

The dual role also exposes Eng to broader transportation questions than the MBTA job alone.

"Phil by and large has been charged with and focused on fixing things," Rooney said, pointing to work fixing subway infrastructure, rebuilding staffing levels and addressing safety issues flagged by federal regulators.

"The role of the secretary begins to take on a little more visionary aspects to it," Rooney said. 

That difference can create tension for someone doing both jobs.

"Someone needs to wake up every morning thinking about that," Rooney said. "And when you're waking up every morning thinking about service and training and hiring and fare collection systems and buying trains, it becomes harder."

At the same time, being secretary places Eng in broader policy discussions, and puts him in a room with other Cabinet secretaries, "all of whom need mobility and transportation" for the sectors they oversee.

While much of his public profile has been tied to repairing MBTA infrastructure, he spent much of his speech to business leaders discussing statewide projects that fall more squarely within the secretary's portfolio.

"On the MassDOT side, the ability to now lean in on West-East rail … and see, how do we move that along quicker?" Eng said.

He also highlighted the replacement of the Cape Cod bridges and reconstruction work on the I-90 interchange in Allston as projects with potential to reshape regional transportation.

"As an engineer, there's nothing more fun than being involved in those types of projects," Eng said. "One could only dream of being involved in one of these in your career... And we have many more."

Rooney said the structure works partly because experienced deputies oversee day-to-day management.

Rooney cited Luisa Paiewonsky, director of MassDOT's Megaprojects Delivery Office, and Jonathan Gulliver, Highways Division administrator and  undersecretary of transportation.

"If I had Luisa in charge of those two big projects, I'd feel pretty good about it," Rooney said of the Cape Cod bridges and I-90 redevelopment. "Gulliver, he's a pro... I'm sure Phil can lean on him quite a bit for the day to day."

Even as Eng outlines ambitious plans, riders on the MBTA network he oversees continue to experience regular disruptions.

Norfolk County Treasurer Michael Bellotti of Quincy echoed frustrations among riders who have not felt the service improvements officials describe.

At Sunday's breakfast in South Boston, Bellotti joked that the three options on the new MBTA spring schedule are "late, very late and canceled."

"Just kidding," he added. "I take the Red Line a lot, and you know it's a good day when the train breaks down near your train station."

Transit riders have faced repeated disruptions tied to infrastructure upgrades over the past three years, with more interruptions ahead. Though service has improved from the safety crises of a few years ago, a disconnect remains between riders' daily experiences and Healey's claims to have "fixed the T."

A major project at Columbia Junction — where the Red Line's Ashmont and Braintree branches merge — requires nightly service changes as crews install a digital signal system to improve reliability and flexibility.

The phased schedule avoids a full shutdown but will still slow trains and force transfers during evening hours for several weeks this spring.

The MBTA and Keolis Commuter Services also announced Monday that commuter rail trains will not serve North Station on three upcoming Fridays for signal upgrades, and for four days during the last weekend of April.

Public comments at recent meetings highlighted ongoing frustrations, with riders describing delays, equipment problems and breakdowns on commuter rail lines.

Last week, a commuter rail train derailed at South Station during a slow-speed incident involving the Providence Line. About 350 passengers were on board, though no injuries were reported.

Eng acknowledged the challenges.

"We know on any given day one thing goes wrong, and it affects a lot of people," he said. "That's why we're rebuilding our infrastructure."

For now, supporters say Eng's credibility may be what makes the unusual leadership structure politically workable.

"You love to see somebody like Phil succeed, because he is so authentic and so committed," said Kate Dineen, executive director of the advocacy group A Better City.

"What we've seen him do here in Massachusetts in a relatively short time is to build trust, both within the MBTA and now MassDOT and within the public," she said.

Rooney said that trust has been reinforced by Eng's willingness to make bold commitments — and deliver.

"If you put out there that you're going to deliver something, you damn well better deliver it," Rooney said, recalling advice he once gave Eng before the transit chief publicly promised to eliminate the MBTA's slow zones.

"And he did it," Rooney said. "So that's what generates trust and confidence."

That credibility has helped stabilize a system long plagued by reliability problems, but it also raises expectations for what comes next.

"It's not by any means, mission accomplished," Dineen said. "But it's very clear to everybody that Phil Eng has moved the system in the right direction."

Sam Drysdale and Katie Castellani are reporters for the State House News Service. Reach them at [email protected] and [email protected].

KELLER AT LARGE: 8:30 a.m., WBZ-TV. Political analyst Jon Keller's guest is Gov. Maura Healey. 

@ ISSUE SIT DOWN: 9:30 a.m., NBC 10. Reporter Matt Prichard interviews Rep. Maggie Goodlander, a New Hampshire Democrat.

ON THE RECORD: 11 a.m., WCVB. The guest is Highway Administrator Jonathan Gulliver.

Do you have an open job you'd like to feature here? Click here to place a job board order, or email Dylan Rossiter at [email protected].

Director of Government Affairs, Jewish Community Relations Council of Greater Boston

Chief Administrative and Financial Officer, City of Holyoke

City Auditor, City of Holyoke

Director of Senior Services, Town of Amherst

Chief People Officer, Boston Public Health Commission

Director of Finance and Operations, Massachusetts Advocates for Children

Director of Decarbonization and Energy Transition, Boston Green Ribbon Commission

Director of Advancement, Strategies for Children

VIEW ALL JOBS