As a 23-year-old junior staffer on Barack Obama’s 2008 presidential campaign, Eric Lesser was tasked with being the future president’s “bag man.” Lesser made sure everyone’s suitcases got from one place to the next as the campaign hopped from city to city. One April morning, he loaded up the U-Haul for a drive from Philadelphia to Harrisburg, Pa., with suitcases and other precious cargo — matzah, macaroons, bottles of Manischewitz and several Maxwell House Haggadahs. 

The campaign was on a whistle-stop tour through Pennsylvania, where Obama would lose to then-Sen. Hillary Clinton a few days later. Given the intense campaign schedule, Lesser knew he wouldn’t make it home to Longmeadow, Mass., for the Passover Seder. So he organized one on the campaign trail.

Twelve hours later, in a windowless basement multipurpose room in the Harrisburg Sheraton, Lesser and other Jewish staffers commenced the Seder. A handful of senior campaign aides, including Obama confidant Valerie Jarrett and current White House Press Secretary Jen Psaki, joined them around the table. 

”Then a Secret Service agent pops his head in and peeks under the table and looks around,” said Lesser. “And then I hear this voice, a very familiar voice going, ‘Oh, is this where the Seder is?’ And it was Obama.”

Once seated, Obama asked attendees about their families’ traditions and their favorite parts of the festive holiday meal. At the end of the Seder, when everyone said “Next year in Jerusalem,” Obama added, “Next year in the White House.”

And so it happened: For the eight years of Obama’s presidency, the original group of campaign staffers continued to meet in the West Wing for a Seder. But by 2016, the group had grown and changed. Younger staffers like Lesser now brought spouses and children. Lesser had finished a stint working in the White House, graduated from Harvard Law School and was serving as a Massachusetts state senator; like a good politician, he showed up to the 2016 Seder with something local — shmurah matzah made in Massachusetts. 

Now, as a candidate for lieutenant governor in Massachusetts, Lesser has more on his plate than handling bags and planning a Seder. 

”I think that there’s a collective feeling in Massachusetts that it’s a great place to live. People are very proud of Massachusetts and our reputation as being leaders on so many issues,” Lesser, 36, told Jewish Insider in a recent interview at a café in downtown Boston. “But it’s really hard to live here. And that’s going to be the heart of my campaign.”

The argument at the heart of the Western Massachusetts native’s campaign is that Boston isn’t the only part of the state that deserves a chance to prosper. “The overall message that I’m going to focus on is that different regions of the state can work together and complement each other,” he explained. 

The Democratic frontrunner for governor is Attorney General Maura Healey, who officially entered the race last week after months of speculation. She has worked in the Boston area her whole career, and Lesser thinks a lieutenant governor from further west than Worcester will even out the ticket. 

“I think that providing a little bit of a sense of regional equity and balance to a ticket is really important,” said Lesser. “The area of the state I represent, the greater Springfield area, is a big area, but it’s often invisible to decision makers on Beacon Hill.”

Lesser enters the race as a four-term state senator, first elected in 2014 at age 29 — then the youngest state senator in Massachusetts. He has joined a crowded field of Democrats vying to become the state’s second-in-command. Other contenders include Salem Mayor Kim Driscoll, fellow Western Massachusetts state Sen. Adam Hinds, state Rep. Tami Gouveia and entrepreneur Bret Bero.

Then-Democratic presidential candidate Illinois Senator Barack Obama (C) checks with staff member Eric Lesser before boarding his campaign plane in Jacksonville, Florida, November 3, 2008. (Credit: EMMANUEL DUNAND/AFP via Getty Images)

Charlie Baker, Massachusetts’s popular Republican governor, has announced he will not seek a third term, creating the best statewide electoral environment for Massachusetts Democrats in years. (Massachusetts is one of six states with an entirely Democratic congressional delegation.)

“People don’t realize we’ve had one Democratic governor in 32 years here in Massachusetts. That’s it,” said Doug Rubin, a Boston-based Democratic strategist. “I think this is a unique opportunity for Democrats to step up.” 

While Democrats elsewhere in the country fret over a midterm election season characterized by growing inflation and plummeting approval ratings for President Joe Biden, Massachusetts Democrats see an opportunity to take the governor’s mansion. The only Republican candidate for governor, Geoff Diehl, is running a Trump-inspired campaign, a move that almost certainly will not gain support in a state where former President Donald Trump earned just 32% of the vote in 2020. (Baker, a moderate Republican, won 66% of the vote in his 2018 reelection — the same percentage Biden received in 2020.)

Healey’s two competitors, Harvard political science professor Danielle Allen and state Sen. Sonia Chang-Díaz, are both running as progressives, while Healey has avoided that term since she entered the race.

Lesser, for his part, has “always identified myself as a progressive,” he said. ”I was a supporter and a co-sponsor of the police reform that we did in Massachusetts last year, which is one of the most aggressive reforms in the entire country. And I did that in an area that’s more purple, but I believed in it, and it was the right thing to do.” 

He intends to win over those skeptical voters by “focusing on those core issues: People feel the prices are going up, they feel rent checks going up, they feel housing going up.” 

“Families are really stressed about childcare,” explained Lesser.

In Massachusetts, the governor and lieutenant governor do not run on a joint ticket; they are elected separately. (If elected, Lesser would be the first Jewish individual to serve in either position.) The lieutenant governor role is viewed by many as a jumping-off point for higher office. The most successful person to do that was John Kerry, who served as lieutenant governor in the 1980s.  

Lieutenant governor hopefuls are “thinking about being in a position where they can cultivate a statewide following and improve their political fortunes,” said Jerold Duquette, a Western Massachusetts resident and political science professor at Central Connecticut State University.

Lesser’s political ambitions took hold his freshman year of high school, when he notched two achievements: being elected high school student body president (a position he held for four years straight) and becoming the youngest member of the Longmeadow Democratic Town Committee. 

“We had to give him a ride,” said Candy Glazer, who chaired the committee for 25 years, “because he wasn’t old enough to drive.” 

One day, Lesser walked into a school assembly to see several teachers lined up in a row, as if in a firing line. 

“These teachers aren’t coming back,” the principal said, the result of statewide budget cuts. ”I remember as a 16-year-old, sitting there and feeling really angry that 14-, 15- and 16-year-olds were paying the price for frankly, bad decisions made somewhere else,” recalled Lesser. 

He undertook an effort to override the budget cuts by getting town residents to vote to raise their own taxes and better fund local schools. He canvassed door-to-door with other students, parents and teachers. But it wasn’t enough. 

“The first vote failed. But something really instructive happened that I’ve always kind of kept with me, which is [that] after the first vote failed, the pink slips went out, and it became very formalized, what was going to happen,” said Lesser. “I sensed that the community’s feelings changed when people saw the stakes, that it was going to be these teachers. So we put another measure back up.”

The second vote passed, and 40 teachers got to keep their jobs.

“I remember him being at the community house watching the votes come in and seeing how happy the teachers were that they could rip up the pink slips,” said Glazer. “That was something that was very unusual for a teenager to do and just caught my attention. And we’ve kept the political friendship through the years.” 

Lesser’s early political activism also owes a great deal to the Jewish community in Western Massachusetts. Born in Queens, Lesser and his family moved to Longmeadow, a town of 15,000 outside Springfield, when he was 7. 

“I remember the very first night we stayed over in the house — it was so quiet, and you could hear bugs,” said Lesser. “We were sort of scared because it felt like a very foreign place.” 

The Lessers eventually adjusted. His parents opened a small medical practice, where his father was a doctor and his mother was a social worker. That upward mobility for his parents, who both grew up working-class, was a big reason for the move. And a desire to help other people in Western Massachusetts achieve that same success has animated Lesser’s time in office. 

“We’ve got a high quality of life. We’ve got a comparatively better cost of living [than Boston],” Lesser said of his part of the state. But unlike Boston, “we don’t have that red-hot economy.”

The policy for which he is best known is the East-West Rail, a transit project to create a rail service linking Boston, Worcester, Springfield and Pittsfield. 

“We actually have gotten pretty close,” Lesser said of the progress made on the project in less than 10 years. “When I first ran for office in 2014, as a 28-year-old, I was laughed out of a lot of rooms. And the idea of connecting the state by high-speed rail was really dismissed as some sort of fantasy. And we just kept at it.”

When the legislature first passed a bill requiring the state to study the feasibility of the project, Baker vetoed it. But now, a commuter train already links Boston and Worcester — and the state is competing for federal funding from the federal infrastructure bill passed last year to build out the rest of the train service. 

“The focus he’s had not just in Western Mass., but in other parts of the state — the East-West Rail, some of the work with gateway cities — that work, I think is incredibly important, and positions him really well in a statewide race,” said Rubin, the Boston-based strategist. 

With more people than ever working remotely, Lesser argues that a rail link connecting the state simply makes sense: People who are tired of the high cost of living in Boston can move out closer to the Berkshires, in the western part of the state, and commute into Boston a couple of times week if needed. “They get on a train and go to Boston. They can do Zooms the whole way back and forth,” he explained. 

Part of this is a ploy to get fellow Western Mass. locals — people like him who left the region as young professionals looking for opportunity elsewhere — to consider moving back home. 

“Eric likes to say, when he speaks to political groups, to people particularly like my age, or parents or grandparents, ‘How many people here have adult children who do not live here?’ And a lot of hands go up,” Glazer said.  

Many young members of the region’s tight-knit Jewish community have moved away as well. “It was a really vibrant place to grow up in terms of Jewish life. But the challenges the Jewish community in Western Mass. has faced are similar to the challenges that the broader community has faced, which is [that] we were an industrial center,” Lesser noted. ”When those jobs left in the ‘80s, ‘90s and 2000s, the Boston area was able to fill in new jobs in tech and in higher ed and education. Western Mass. has done some of that, but it has obviously not been done at the same pace.”

The Springfield metro area has a strong, historic Jewish community (“the public schools were closed on Rosh Hashanah and Yom Kippur,” Lesser noted), perhaps best known for serving as the home of the Harold Grinspoon Foundation and the headquarters of the nonprofit PJ Library. Growing up, his family was active in a local Reform synagogue, and that’s where Lesser’s interest in social justice and political advocacy was kindled. 

He participated in a Black-Jewish dialogue with a local Baptist church, and as a member of his synagogue’s NFTY youth group, he participated in action campaigns with the Religious Action Center of Reform Judaism. In April of 2002, as a high school student, he traveled to Washington to join a pro-Israel march on the National Mall that drew tens of thousands of participants at the height of the Second Intifada. 

In 2008, Lesser traveled with Obama to Israel for a brief campaign visit, which was followed by a stop in Berlin. ”It was not lost on me that I was on a plane with potentially the first African American president leaving Israel on the way to Germany,” recalled Lesser. “I thought about my grandparents and what they would have thought,” he added. “Only in America.”

Later, he traveled to the Jewish state on a delegation of Massachusetts legislators. (”We introduced him as the Seder guy,” said Jeremy Burton, executive director of the Jewish Community Relations Council of Greater Boston, which organized the trip.)

“It’s very different going in an official capacity. One of the things that struck me is, it’s a very important relationship for Massachusetts,” Lesser said of the state’s connection to Israel. Several hundred Israeli companies operate in Massachusetts, employing people across the Bay State, and Lesser was pleased to learn the extent of the business and cultural ties between the states. “Certainly something as lieutenant governor I’d want to do is to continue to strengthen those ties.”

Combating hate crimes and bias incidents has been a priority for Lesser, who helped create a nonprofit security grant program in Massachusetts, modeled off a similar program at the federal level. The program began with $100,000 in 2018. Four years later, the program has $2.1 million to award to “nonprofits at risk of terrorist or hate violence: LGBTQ organizations, African American churches, mosques, synagogues and religious centers,” he explained. 

Ultimately, it’s an understanding of the nitty-gritty parts of the policymaking process that Lesser wants to bring to the job of lieutenant governor. “I’m the only candidate that has really extensive federal experience, and historically, a big part of our job has also been helping to work on the nuts and bolts of getting the federal money to the state.”

State Sen. Eric Lesser with state Rep. Cory Atkins

What Lesser actually did when he worked for the federal government was a bit different. “He was upbeat, positive, friendly, obviously bright and inquiring,” David Axelrod, a senior advisor and close friend to Obama, who hired Lesser as an assistant when Obama became president, told JI. “He always got our bags to the right place at the right time, so I figured he could probably get me to the right place at the right time in the White House.”

His job was to make sure Axelrod could keep everything together. Not infrequently, he had to draw upon his knowledge of stain removal. 

“I’m not the most fastidious person in the world. I’m famous for spilling stuff on myself,” Axelrod admitted. “Eric always kept club soda nearby. He would race in there like a volunteer fire department, because I’d have to go on TV or I’d have to be somewhere and, you know, having a big block of oatmeal on my jacket was not desirable.” 

It’s a gig that could have been scripted into “Veep,” the HBO sitcom that skewered American politics. Lesser would know: He served as a consultant for the show throughout its seven-season run. He loves the show, and like any good political junkie, he has strong opinions on the three seminal political shows of the last two decades — “Veep,” “The West Wing” and “House of Cards.” 

Like the other activists and political insiders who came of age during the optimistic Obama era of “Yes, we can,”  Lesser’s favorite of the three shows doesn’t come as a surprise. 

“’House of Cards’ is too cynical for me,” Lesser admitted. “I’m a diehard ‘West Wing’ fan.” 

Jed Bartlet — the earnest, idealistic president in “The West Wing” — got his start in New England politics, too.