An August 8 forum for the District 6 Boston city council seat, sponsored by JP Progressives, with candidates William King (top right), Kendra Lara (lower right), and Ben Weber (lower left). Journalist Yawu Miller (upper left) was a moderator.

A LITTLE MORE than a month ago, the Jamaica Plain Progressive’s endorsement in the District 6 race for Boston City Council lost its status as a golden ticket for winning over Jamaica Plain, Roslindale, and West Roxbury voters. The group’s endorsed candidate, City Councilor Kendra Lara, finished dead last in the three-way preliminary election, while her rivals who were denied the endorsement, Ben Weber and William King, took the top two spots and advanced to the November 7 final election.

Despite being a co-chair of JP Progressives at the time, I was frequently out of step with my fellow steering committee members – and perhaps never more so than when it came to being the lone dissenting voice in the endorsement vote of the group’s steering committee in this race.

However, I was, I later would learn, in step with how many people in District 6 voted. By harmonizing these varied perspectives with hindsight, I will try peeling back the onion layers to offer my take on what went wrong and how JP Progressives can reconnect with a majority of voters in the district. This granular case study may also impart broader lessons for progressives in Massachusetts.

A mere two years ago, first-time candidate and Jamaica Plain resident Kendra Lara (then Kendra Hicks) won in a bruising race against the formidable Mary Tamer, a former school committee member living in West Roxbury, signaling the arrival of a dynamic new force in Boston politics.

The constituencies Lara personified and elevated—Afro-Latina women of Dominican descent, Jamaica-Plain-born, renters, single-parents, parents of children with special needs, non-affluent—despite their growing ranks, lacked fiery representation.

At only 31-years-old, Lara’s ascendancy answered myriad prayers.

During her first term, Lara proved even smarter and more policy-oriented than anticipated. Detractors, though, recoiled at what they viewed as an abrasive style. Notably, Lara spent her one free please-give-me-a-second-chance chip early, by recycling an antisemitic trope, then asking the public for forgiveness.

Nonetheless, a city councilor facilitating a conversation involving the ungentrified and gentrified residents of Jamaica Plain, Roslindale, and West Roxbury felt overdue and important, and continues to be important.

All these distinctive considerations weighed on the JP Progressives steering committee as it charted a path forward on Lara’s reelection quest before Lara’s car accident on June 30.

For nearly 15 years, JPP, a valiant volunteer-run organization, has performed a scarce public service—offering a forum for voters to ask questions and for candidates to shine or falter under scrutiny. Candidates from governor to state representative have sought the group’s endorsement, presenting the steering committee with many challenging choices over policy priorities. Inevitably, though, we persevered.

So we felt confident that the culture we had built – resilient, deliberative and collaborative – would survive the vortex the race for District 6 City Councilor would unleash. But we were wrong.

City Councilor Kendra Lara speaking at July 19, 2023, Boston City Council meeting.

Nothing in our track record, not the race for mayor between Marty Walsh and Tito Jackson (JPP endorsed Walsh) nor the race for state representative between Jeffrey Sanchez and Nika Elugardo (we endorsed Elugardo) nor the race for mayor with Kim Janey, Michelle Wu, Andrea Campbell, John Barros and Annissa Essaibi George (JPP didn’t endorse), had trained us how to navigate this perfect storm.

By nightfall on June 30 news was spreading rapidly that Lara had crashed into the house of a constituent – a retired school teacher – after swerving to avoid another motorist exiting a parking space. The immediate result involved injury to a child passenger, severe damage to a house and a totaled car, but luckily no loss of life. The spectacular accident soon led to a litany of eight charges against Lara, including speeding, operating an unregistered car without a valid driver’s license, and a charge related to improperly restraining a child.

Jamaica Plain Progressives takes pride in managing a rigorous endorsement process consisting of six distinct stages—a private informal candidate coffee, a written questionnaire, a public candidate forum and a public community conversation. For clinching the endorsement, a politician must garner two-thirds of the steering committee votes followed by 60 percent of the votes cast by the broader membership.

The issue facing the group: how to test and trust a progressive rising-star woman lawmaker accused of lawbreaking squaring off against a pair of viable male candidates? Ben Weber is an experienced worker’s rights attorney of Jewish descent and William King is an experienced IT professional and a Black man. Together with the incumbent Lara, the September 12 preliminary election ballot would list three capable individuals, each reflecting valid stripes on the ideological spectrum—Lara absolutely progressive, Weber solidly progressive and King solidly Democrat (or, if you like, a centrist with select progressive positions).

The steering committee, operating in the shadow of a string of “ethical lapses” by local progressive leaders and, nationally, of bitter political polarization, Donald Trump’s war on truth and fierce MAGA denialism, held a real opportunity to untangle a serious matter.

Instead, we fell short.

The organization would hold two key endorsement votes, with the steering committee voting to endorse Lara on August 23 and the overall membership doing so on September 9.

In my view, over a longer timeline the steering committee took five well-meaning missteps.

First, we mostly consented to shaping a polite interviewing approach toward the charges against Councilor Lara that aspired to respect her privacy and honor the principle of innocent until proven guilty. Ironically, though, this aversion to direct factual questions would backfire as it delayed Lara the opportunity to explain her side of the story.

Take, for example, JPP’s online candidate forum on August 8 where Lara faced only one substantive question on the matter, the elephant-in-the-room topic foremost in many voters’ minds.

Second, we mostly promoted a version of “pure policy politics” that accurately mirrors JPP’s focus on policy, but eclipsed other criteria many voters value like judgment and collaboration. A way this manifests is in our signature written policy questionnaire, where we pose precise questions to discern if a politician shares our agenda. Extensive quizzing at the forum helped Lara establish superior policy congruence and fluency with our priorities. Yet it inadvertently sparked identification with Weber and King among viewers who found the strict scoring of policy-only progressivism overly reductive.

Third, we mostly rejected invoking citizen-empowerment tools like a conditional endorsement or withholding the endorsement to require Councilor Lara to fully satisfy any lingering concerns stemming from the crash and charges. By leaning into our power to renew, suspend, or rescind support, community groups like JPP can demand better rather than accepting less.

Any elected official accused of lawbreaking must speak to both the courts of public opinion and law to win reelection. Harshly, this reality especially clings to politicians of color, like Councilor Lara, who endure the slimmest margin for error when accused.

A paucity of information meant that JPP members met for our community conversation ritual groping for answers. It was August 23 when over 100 people joined a virtual forum expertly facilitated by a pair of steering committee members. The attendees wrestled with the question of what was the right thing to do. Though some were unequivocally pro- or anti-Councilor Lara, many were undecided about endorsing anyone at this time.

But my fellow steering committee members already had made up their minds.

To my dismay, I’d become the lone outspoken dissenter, arguing against an endorsement of Councilor Lara because I felt it was premature, inconsistent, or plain wrong, given the gravity of the issues of judgment and behavior surrounding the crash.

The near–consensus on the steering committee could be best summarized as we’re “choosing to believe Councilor Lara. We’re believing in hope. We’re trusting in hope.” While this sounded good in theory, the repercussions meant that we would rely on private explanations from the candidate regarding the different charges.

I pressed for more corroboration, transparency, and separation from the campaigns. Unless the identical information being shared with the steering committee was also being shared with voters and the Weber and King campaigns concurrently, we risked being a captured entity instead of an independent authority or civic resource.

When my call for transparency failed, I considered whether resigning in protest would motivate my friends to reconsider the risks. Instead, I decided to wait until after the preliminary so I could keep trying to make a difference on the inside.

During the ensuing few weeks, several steering committee members stayed in close contact with the Lara campaign, pressing her for more public communication about the details behind the charges, encouraging her to retrieve data from the car’s “black box” expeditiously. Ultimately, the Lara campaign’s inaction caused concerned backers externally and within JPP to intervene by pledging funds to obtain her car’s black box report, which indicated she was travelling 27 miles per hour in a 25-miles-per-hour zone.

Fourth, we mostly silenced dissent when readying to persuade our members to support the endorsement pick. While I asked to write a brief dissent—and was denied permission to do so then—now I know some friends also harbored misgivings they hid. Progressives should welcome complexity and pluralism within our ranks.

Fifth, we occasionally succumbed to a version of “tunnel-vision politics” that prioritized short-term thinking. By fixating on having a rising-star progressive retain this seat, we lost the peripheral vision to recognize we could be squandering our special sauce for turning out voters on behalf of other quality progressives we endorsed this cycle, like Ruthzee Louijeune and Julia Mejia, two skilled at-large city councilors meriting reelection. Our capability to mobilize depends on our hard-earned credibility.

To be sure, the Steering Committee deserves lavish praise for volunteering so much time, thought, and energy to enhance civic life. And praise for administering the endorsement voting cleanly and resisting credible pleas to extend the voting in light of the crash lab report news. Councilor Lara nevertheless crossed the original finish line and punched the perceived “golden ticket” by surpassing the threshold of 60 percent of member votes.

But on September 12, came the electorate’s chance to speak: Weber finished first (4,951 votes), King second (4,384 votes), and Lara last (2,351 votes).

I resigned as co-chair of JP Progressives after the election.

By absorbing this case study, flummoxed progressive organizers can rebound.

The ordeal is a stark reminder that in a heavily Democratic state like Massachusetts, progressives would be best served by encouraging robust dialogue that includes personal attributes as well as policy, and moving from loyalty-based relationships with politicians to arm’s length accountability-based relationships so we can regain the public’s trust and force politicians to be the best they can be.

Ed Burley served as co-chair of JP Progressives from 2019 until resigning in September. He is a civil rights attorney and entrepreneur who serves on the Democratic State Committee.