Oliveira, senator for all seasons, even dark ones. (WMP&I)

SOUTH HADLEY—Despite a life of activism in politics, State Senator Jake Oliveira’s state electoral career only just began. He took office as a state rep in 2021 and matriculated to the State Senate two years later. However, his sophomore term in Beacon Hill’s upper house will differ from his previous two in the legislature.

There was a Democratic president in Washington for the last four year. Now, Donald Trump anarchical and vengeful second term is reverberating into Massachusetts. Oliveira has particular concerns about the impact on the Hampden, Hampshire & Worcester Senate district, especially in the realm of health care. Still, he has a lot on his to-do list above and beyond blunting the chaos from the feds.

“People can’t turn a blind eye to what this administration is doing,” he said. “They need to continue to advocate. They need to continue to be present and contact their federal officials to ensure that we have voices in Washington, DC that represent our needs.”

Vengeance is a less obvious threat to Western Mass—in contrast to the City of New York. Rather, Trump and Elon Musk’s broader agenda of hollowing out health care and education while abusing—or even erasing—minority groups stalks the 413. Bay State Health Systems is the largest employer in its district. Out all of its revenue, 71% comes from Medicare and Medicaid. Among Oliveira’s constituents are hundreds of employees at the region’s colleges.

Beyond the threats from Washington, there are ongoing needs, too. Massachusetts may be better able to withstand both the chaos and tend to other issues, thanks to its bond rating. Yet, voters still expect progress on transportation, like East-West rail, and funding for education.

Oliveira, 38, spoke to WMP&I in February, just before the heat on the chaos and damage of Trump’s new regime was coming into focus. Democrats on all levels have faced criticism for not doing enough. It was torrent that did not appear to break until this month as US Senators began taking action and sounding the alarm more overtly than ever.

On Beacon Hill, the response has been mixed. Senate President Karen Spilka has developed a war room of sorts. By virtue of her position, Attorney General Andrea Campbell has taken on the most prominent role. Like now-Governor Maura Healey had been during the last go-round, Campbell, as the commonwealth’s top-ranking legal office, has turned to the courts to curb Trump’s serial lawlessness.

Speaking to WMP&I over lunch in South Hadley between official stops, he applauded Campbell’s efforts. However, he also pointed to his own interactions with constituents. For example, shortly after the election, Belchertown family with a trans child expressed their deep fears about the then-impending administration. Oliveira’s usual affability and folksiness dissolved into anger he rarely displays, save the campaign trail, if even then.

“The rhetoric that they’re using to just make people feel less than is what I find the most disturbing,” he said.

Oliveira’s district in green. (via malegislature.gov)

Oliveira’s district is largely safe seat for Democrats. It includes parts of Chicopee and Springfield and all of Belchertown, East Longmeadow, Granby, Hampden, Longmeadow, Ludlow, Palmer, South Hadley, Warren and Wilbraham. Among these communities are some Trumpy confines, including Oliveira’s native Ludlow, where he was once a School Committee member. This has not deterred him, though.

“I’m ready to go to bat for Western Massachusetts to ensure that this administration does not roll back the protections that we have.”

Oliveira had been active in Democratic politics and public education—he worked for the state university council—long before he veered into the legislature. He ran for the House in 2020 after longtime Ludlow Rep Thomas Petrolati called it a career. One term later, Eric Lesser retired from the Senate. Oliveira succeeded him after a spirited if hardly close primary.

The transition has been positive, Oliveira said, noting that senators get a few more staffers—and more responsibility. Going from the House, where he had one staffer, to the senate, where he has upwards of five, provides perspective.

“You have an appreciation for every role in your office, and you have an appreciation for the job itself, because you live and have done every single role within the office,” Oliveira said.

Moreover, the looming threats aside, Oliveira has pointed to tangible progress in several key areas. He extolled the potential for rail service to Palmer follwoing the state’s selection of site for a train station. The state has not yet allocated full funding to build the facility. There are other hurdles from the fickleness of federal money to local complaints about the site choice.

Amid all the darkness, 2025 did bring a bit step forward for rail in Palmer. Above is the site for the new station. (via MassDOT/palmertrain.org)

Still, Oliveira said he was working with the town’s stat rep, Republican Todd Smola to make it happen.

“We are both committed to making sure that in the next few fiscal years, whether it’s bonded funding or direct funding that Palmer is prioritized,” the senator said.

As the only station that could exist between Springfield and Worcester for the foreseeable future, it will necessarily play a part in the expansion of rail service between Massachusetts’s capital and its occident. That effort is itself slow-going with service not beginning until 2029. It will start with only two additional round trips, complementing the existing Boston to Chicago Lake Shore Limited.

Yet, Oliveira does not expect things to stop there. As others have, he liked the service to the explosive growth the Portland, Maine to Boston Downeaster has seen.

“That’s why the track improvements are the most important part of this, because you’ve laid down the infrastructure to make it reality so you can build on it in the future,: he said. “I don’t see this as stopping at 2029.”

They swear they were busy last year. (WMP&I)

On the legislative front, Oliveira touted victories last session. The legislature came under heavy criticism in 2024 after it hit the end of formal session without finishing dozens of keys bills. It was a frustration Oliveira says he shared. However, he also said that after the House and Senate reopened formal session, it became especially productive.

Among the things he touted was Ollie’s Law, cosponsored with Longmeadow Rep Brian Ashe, that regulates canine daycare center. (The eponymous Ollie was killed by other dogs where had been kenneled). The senator also highlighted a prescription drug affordability bill that became law. The Municipal Empowerment bill did not become last session. Yet, Oliveira said he added language to Governor Healey’s bill to ease procurement for municipalities.

“The other big thing that I’ve been advocating for, for literally my entire adult life and student life, that we got over the finish line this time is free community college,” Oliveira said.

Beacon Hill vastly expanded access to community college by making classes for many students tuition-free. The region’s community colleges have seen jumps in enrollment. Oliveira also said the legislature provided wraparound services to help this new student population.

Funds from the Fair Share Amendment, or Millionaires Tax, funded the community college expansion. The amendment to the state constitution required the funding go exclusively to transportation and education. However, it left the split up to the legislature.

Since its enactment, there has been a slight skew toward education. Some have called for more to go to transportation. Oliveira did not explicitly endorse that move, but he indicated it may be appropriate.

Oliveira as a Senate frosh in 2023. What will his sophomore term bring? (WMP&I)

“When you look at where Massachusetts ranks as a state in comparison to other states and rankings, we’re number one in education, number one in health care, we’re not number one in transportation, and that is something that is not a point of pride of ours,” he said.

Still, he does not want to over-correct either and has filed legislation to address the long-term stability of special education.

Even with the bombardments from Washington, Oliveira said he had lots to look forward to this session. Despite—or perhaps because of—the overwhelming Democratic advantage in the legislature, there is a fair amount of collaboration across party lines. They made progress, however incremental, on housing last session and he expects costs to feature prominently as well.

“I’m excited that we have legislators that aren’t there just to go on social media or to run to the press to state their position, but are actually there to roll up their sleeves and get things actually done to improve the quality of life,” he said.