....For Brookline, the episode was deeply off-brand. It is a regular competitor in magazine listicles of the best places to live in the nation, if you can afford the high real estate costs and cope with the community’s proud busybody nature. (It’s also been named at least once among the “snobbiest” towns in the country.) Democratic voters outnumbered Republicans by upward of five to one in the March presidential primary, and Brookline has consistently led the charge on progressive causes. Over the past 15 years, the town has banned plastic bags, Styrofoam, and trans fats; eschewed police stun guns; floated a tax on sport utility vehicles; debated the merits of the Pledge of Allegiance in schools; and even committed the sacrilege of dissing Dunkin’ Donuts when the chain wanted to set up shop along its suburban streets. Brookline, says town counsel Joslin Murphy, is a “beautiful oasis” in the Boston-area rat race, “a very educated town comprised of citizens who are deeply interested in social justice.”

An outspoken group of public servants and residents, however, say that such lofty ideals have little to do with actual town practices, and claim that racism within the police department is perennial and not simply isolated to one or two embarrassing and hateful incidents. As a result, Pilot and seven other police officers and firefighters have filed lawsuits in state and federal court alleging a “longstanding and well-established policy” of racial discrimination in the town. Many residents have spoken publicly or made court claims detailing their experiences with racial profiling and discrimination, and an April survey found that members of the town’s mostly white officer corps considered the department rife with nepotism. In January, the town’s own Commission for Diversity, Inclusion, and Community Relations declared that the board of selectmen was at fault for allowing “a culture of institutional racism” through its personnel decisions.

And yet Brookline administrators have been dismissive of the notion that the town has a racism problem that they have failed to address. Murphy, a former Brookline police officer, declares that the “town truly cares about these employees and very much hopes that they can return to work in a way that they are satisfied with.” But in nearly the same breath, she criticizes the attention that the employees’ discrimination claims have received, saying that their lawsuits are “weak” and that “when that’s the case, plaintiffs tend to lean toward public pressure.”

Pilot, who now chops trees in the Berkshires to make ends meet, is far less sanguine. “You can quote me on this,” he says. “I’m calling Brookline a fake-ass liberal town.”....allegations of police profiling and harassment persist. Dwaign Tyndal, a member of the town’s diversity commission, relocated to Brookline 12 years ago for its excellent public schools and idyllic setting—that perfect little village nestled a short drive from downtown Boston. Yet, he says, conversations with other black Brookline residents inevitably circle back to how certain areas—such as Coolidge Corner—are notorious for traffic stops that reek of racial profiling. “Those are the areas,” Tyndal says, “where it gets communicated to you in different ways that you aren’t invited here.”

Arthur Conquest, a black man who has lived in Brookline for 34 years, agrees that if you’re black or Latino you should expect to be stopped by police when walking along the town’s streets. “All this business about the town being liberal, the town being progressive, and them being committed to diversity, it’s absolutely nonsense,” he says.

Proving racial bias in traffic stops is notoriously thorny, but statistics collected by the police department do show that black people make up a significant portion of those stopped in Brookline. In 2015, for example, Brookline officers performed 76 “field interrogations” of people who were stopped for what they deemed to be suspicious activity. In a town where roughly 3 percent of residents are black, 23 of those stops—or 30 percent—were of black people.