On Tuesday morning, Steve Tompkins presided over a town hall event at the Suffolk County Sheriff’s Department in Boston. The participants were Senator Ed Markey and Representative Joe Kennedy III, candidates in the September 1 primary that will effectively decide November’s Massachusetts Senate race. The audience consisted of Suffolk County inmates, who addressed the sheriff with deference as they approached the podium to pose their questions. One of the candidates was Tompkins’s sometime boss: The Kennedy campaign appointed him as an adviser in early June, having secured his endorsement in October 2019.

“Keep it kind of succinct,” Tompkins told Kennedy. “Politicians will go on and on and on.”

“Last time I checked, Sheriff, you got elected too,” Kennedy shot back. The room broke out in polite laughter.

Kennedy was right. Tompkins did get elected—and then fined by the state ethics commission for using coercive tactics. In 2013, he flashed his badge, thus exerting his authority as a police officer, to dissuade local businesses from publicly supporting his opponent. The fact that Tompkins is not just a cop but one with a documented record of exploiting his power makes him a strange choice for a senior adviser for “racial and economic inequality and criminal justice reform.” The Kennedy campaign announced his appointment on June 3, just as the movement for Black lives swept the country in the wake of George Floyd’s murder.

The Kennedy campaign posits the fossil fuel and pharma stockholder’s challenge to a coauthor of the Green New Deal as an upset from the left and has often lambasted Markey for votes from previous decades, including one in favor of Bill Clinton’s 1994 crime bill. To be sure, the bill had a disastrous hand in mass incarceration and systemic racism, but it was also widely popular—or at least effectively caucused—passing 95 to four. “The liberal wing of the Democratic Party is now for 60 new death penalties…100,000 cops…[and] 125,000 new state prison cells,” boasted then-Senator Joe Biden at the time.

But if we’re nitpicking over odious yea votes, Kennedy has a far more recent one on his record: In 2018 he voted for the Protect and Serve Act, known more colloquially as the Blue Lives Matter bill. As the ACLU and 27 other civil rights and government accountability organizations noted in a condemnation, the legislation “perpetuates a false narrative that police are under increasing attack by their communities” but “does not call for support services, better training, improved safety measures, increased supervision, or any of the other multiple measures available to law enforcement that are widely accepted as promoting officer safety and wellbeing.” Instead, it increases already harsh penalties for causing harm to cops, including up to 10 years in prison for “serious bodily injury” and potential life imprisonment for killing or threatening to kill a police officer—leaving interpretation of those subjective terms up to the courts.

The act never made it to a vote in the Senate, so Markey never had a chance to share Kennedy’s mistake. But unlike his challenger, the incumbent has spent the years since his 1994 vote introducing reams of transformative legislation. Though his signature issues, environmental justice and technological equity, are not directly related to criminal justice, pursuing clean water and energy in marginalized communities and curbing the reach of surveillance technology have profound racial effects. And last week, Markey introduced the Ending Qualified Immunity Act with Senators Bernie Sanders and Elizabeth Warren, seeking to eliminate the legal protection that insulates police from accountability for their on-duty crimes and civil violations.

As Markey explained during the July 7 town hall, “just after the Civil War, there was a law passed that you could sue [the police], and over the years, the Supreme Court has been chipping away it.” Enacted as the 1871 Ku Klux Klan Act, the law that led to qualified immunity actually sought to protect civil rights and increase police accountability, but starting in the 1960s, the Supreme Court handed down a series of decisions that expanded the arguments law enforcement could use to avoid legal consequence—from “good faith” to “objective reasonableness” to near-total immunity. “So we need to overhaul the whole system,” Markey said.

As with many issues, Kennedy has chosen to take Markey’s side on this—he signed on to cosponsor the bill’s House complement introduced by Ayanna Pressley and Justin Amash. But introducing his own legislation has never really been Kennedy’s thing. Since entering Congress in 2013, he has sponsored 60 pieces of legislation, including bills, resolutions, and amendments. In the same period, Markey has sponsored 505—more than eight times as many.

Perhaps Kennedy’s lack of legislation can be chalked up to his lack of experience. He is, after all, far newer to Capitol Hill than Markey, as his campaign loves to stress. (The multimillionaire candidate is “young, scrappy, and hungry,” according to Students for Kennedy, referencing the musical Hamilton.) But when we look at his earlier experience, the picture doesn’t improve. As a prosecutor, Kennedy worked under Michael O’Keefe, the conservative Republican district attorney for the Cape & Islands who, as Will Isenberg put it in The Appeal, “never met a form of criminal legal system reform that he didn’t hate.”

“The cases [Kennedy] tries usually don’t make the papers,” noted a fawning Boston Globe profile of Kennedy in 2011. “As the new guy, it’s up to him to drag stacks of files across the parking lot, to rotate among the district courts, to follow the lead of his senior colleagues,” said the Cape Cod Times the year prior, in a story characterizing the young prosecutor as a “public servant.” To be the “new guy” working under a tough-on-crime DA from 2009 to 2011, when Massachusetts was in the middle of a foreclosure crisis, “following the lead” in unexciting, run-of-the-mill cases would require collecting quality-of-life fines, securing low-level drug convictions, and evicting families from their homes. Working for O’Keefe meant working for the criminalization of poverty.

Now boasting what Isenberg calls “a criminal justice platform that any reformer could love,” Kennedy seems to have reversed course, and surrounded himself with a loyal team ready to groom his every statement. When Kennedy stumbled during the livestreamed debate, Tompkins stepped in to help. After one attendee used his own case as an example to press the candidate for specifics on how to increase police accountability, the sheriff cautioned, “I invited both candidates here to have a discussion about how they are going to handle the office of senator. And as much as your particular cases are seriously important, that is not the nature of this gathering.”

Markey, who spoke first, spent his hour discussing his bill to end qualified immunity; his cosponsorship of the Next Step Act, Cory Booker’s plan to reduce sentencing and recidivism; his Covid-19-relief Universal Basic Income bill with Sanders and Kamala Harris; and his legislation with Pressley to provide free public transportation. During his turn, Kennedy mostly avoided legislative specifics. “Hey, I don’t have all the answers,” he admitted.

“Ed Markey agreed to a debate moderated by a sheriff who has endorsed his opponent and who is hired by Joe Kennedy as an advisor,” commented one Facebook viewer. “That’s how bad Joe Kennedy is at debating.”

While it may seem odd that Markey would agree to a conversation hosted by his opponent’s ally, Tompkins stressed that he has sought opportunities for his inmates to speak with candidates in the past. On Twitter, Suffolk County District Attorney Rachael Rollins agreed. Responding to the question, “Why is Sheriff Tompkins moderating a Senate candidate debate when he’s a senior advisor to one of the candidates?” Rollins wrote, “The same reason he hosted a forum back in the 2018 Suffolk County DA’s race, having already fully endorsed one of the candidates. Give you a hint, it wasn’t me.” (Rollins, who endorsed Markey, has earned the ire of several right-leaning state officials for her refusal to prosecute low-level offenses, with the goal of decriminalizing poverty-based crimes. One of her critics is Kennedy’s old boss O’Keefe, who disdains what he dubs “social justice district attorneys.”)

“There is a Kennedy family tradition of nepotism,” wrote Robert Kuttner in The American Prospect, “and sometimes it has worked out.” It threatens to do so again. When second-quarter fundraising results were released on July 1, the candidates were in an almost perfect tie. Polling remains limited, but it shows Kennedy leading.

At the Suffolk County Sheriff’s Department, cries of nepotism didn’t seem to have hurt. As Kennedy approached the applauding crowd after closing remarks, the person running the livestream giggled. “I like him,” said a voice near the mic.