Legal marijuana is winning. But getting an arrest off your record isn’t so easy.

Khalil was riding in a car in a Boston suburb with his brother and a friend in 2003 when, he recalls, a police cruiser “put the lights on us and pulled us over.”

The officer claimed that their vehicle matched the description of one involved in a shooting. According to the police report, as the officer approached the car, he saw Khalil “moving about in his seat in an apparent attempt to conceal something.” The officer told Khalil to get out of the car. As he patted him down, he noticed a substance, he would later write, that “through training and experience” he believed could be a package of illegal drugs.

Out of Khalil’s pocket came a small baggie of marijuana — and then out came the cuffs.

Seventeen years later, Khalil, now 44 and living in the Dorchester neighborhood of Boston, still enjoys pot. He likes to smoke and listen to music, typically hip-hop, like Griselda and Freddie Gibbs, or R&B (“anything soulful,” he said). Until 2016, Massachusetts had alternately ticketed, fined, arrested, charged, convicted, and incarcerated people for possessing, using, or selling marijuana. Today, smoking pot while listening to music — or having a small baggie in your pocket and going for a drive — is legal.

Khalil still calls BS on his nearly two-decade-old arrest. His lawyer, too, has noted the proliferation of “pretextual stops” made against Black and brown people in the state. Among the three people riding in the car that day back in 2003, only Khalil was convicted of a crime, for possession of less than a quarter-ounce of marijuana. That conviction continues to cast a shadow over his life.

In 2019 alone, more than half a million people across the country were arrested for simple possession of marijuana, which is more than the total number of people arrested in the same year for all violent crimes combined. Most of the people caught up in that onslaught of criminalization were Black and brown; studies have shown that Black people, on average, are nearly four times more likely to be arrested for marijuana possession than white people, even though both use marijuana at similar rates.

After decades of pushback — of calls for justice, pleas for rationality, and scientific studies finding benefits of marijuana use for pain management, the regulation of seizures, and the treatment of PTSD, Parkinson’s, multiple sclerosis, and nausea, among many other chronic conditions, with minimal side effects and little risk of addiction for adults — states, including Massachusetts, have begun to roll back the criminalization of pot.

In 2014, Colorado became the first state to legalize recreational marijuana use and sales, opening the doors to a cottage industry of growers, chic dispensaries, weed delivery services, weed vending machines, and even pot tourism. Today, legal sales top $1 billion a year in Colorado, contributing hundreds of millions in tax revenue. Ten other states have since followed Colorado, and in November, voters in four more states approved legalization ballot measures to do the same in coming months.

The wins for marijuana advocates reflect a sea change in cultural attitudes toward the drug, putting it on par with cash cows such as alcohol, cigarettes, and gambling. An exultant, and lucrative, plume of marijuana smoke seems to be hovering in the air. But the movement for legalization isn’t just about destigmatizing a plant and sorting the profits. It’s about halting the panoply of harms still being exacted — racially targeted overpolicing, mass incarceration, and vilification of drug users — and about building a more equitable future.

To achieve that idyllic future, reformers aren’t gazing only at the just pastures on the political horizon. They are also looking to undo the past wrongs that have shattered lives.

On the campaign trail, both President-elect Joe Biden and Vice President-elect Kamala Harris repeatedly mentioned the idea of expungements, or the retroactive erasure of past convictions for low-level marijuana offenses, mostly possession. And the Marijuana Opportunity Reinvestment and Expungement Act (The MORE Act), which would simultaneously expunge convictions as it legalized marijuana at the federal level, sailed through a vote in the Democratic-controlled House of Representatives this month (though its passage in the Republican-led Senate is believed to be unlikely).

But the story of Massachusetts reveals the shortcomings of piecemeal legalization efforts for those who’ve been harmed by the drug war. Sometimes those in power shoot the confetti on legalization and only then seem to remember that people are still chained by old convictions or remain imprisoned. As marijuana use is legalized and normalized — as a new industry is born, as Grandma openly smokes to ease her arthritis and Mom and Dad pop weed gummies after the tykes are tucked in — Khalil still can’t get a job because of a 17-year-old marijuana conviction.

When Massachusetts legalized marijuana in 2016, legislators didn’t initially address what to do about those who had racked up minor pot convictions before our new era of cannabis enlightenment. After grassroots efforts and leadership from community and state criminal justice advocates, a new and complicated 2018 statute set up a system of expungement, but Khalil’s attempts to clear his record have been, so far, a halting and unsuccessful fiasco. (Vox is using Khalil’s Muslim name, not his legal name. Fearing continued discrimination, he and his lawyer requested that his legal name not be published.)

In practice, not only do those seeking expungements need a lawyer to secure one, but they are also subject to the whims of a judge who must rule that clearing a record is “in the interest of justice.” An unconvinced judge and delays provoked by the coronavirus have dragged Khalil’s case on for more than a year.

According to NORML, a marijuana legalization advocacy group that has been working on the issue for 50 years, across the country, there are hundreds of thousands, perhaps even millions of people like Khalil whose past marijuana convictions continue to weigh on their lives like millstones. “You have countless lives that have been ruined,” said Kimberly Napoli, an expungement advocate, Massachusetts Cannabis Advisory Board member, and one of the key players in the state’s legalization movement. In other words, expungement advocates and marijuana policy reformers have a lot of un-ruining to do.

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Khalil doesn’t remember the details of the second time he was charged with marijuana possession, which took place three years later, in 2006. He only knows that it was one of the dozens of times — more than 20, in Khalil’s estimation — that he has been racially profiled and stopped and harassed by the police. “Just me being out in the street and the cops just profiling me,” he explained. Police, he told me, “don’t like to see a bunch of Black people congregating. It’s especially true for Black men … even on your own street.” And, with pot in his pocket again, he got his second marijuana charge.

Despite his vexed history with the plant, Khalil said simply, “I enjoy recreational smoking, and I don’t see myself stopping.” That’s where he is now, though he’s taken breaks in the past, and does so every year for Ramadan. He’s thought about quitting, he said, anytime his “financial situation started looking funny.” As he’s struggled to get or keep employment over the years, it’s been “funny” a lot.

A father of three, Khalil is a self-described family man. He keeps it low-key, doesn’t party, and harangues his neighbors about keeping the stairwell just outside of his apartment door free of trash and hard drugs. He and his girlfriend like to toil over abstract and complicated jigsaw puzzles — in mid-October, one was partially pieced together on the table, another glued in completion and hung on the wall. A collection of toy figurines made out of spray-paint can lids peopled the mantle under a flat-screen television. “We’re really into art and self-expression in this house,” Khalil said. At the squat coffee table in front of the sectional is where he smokes.

Khalil grew up in a two-parent home in the nearby middle-class neighborhood of Mattapan. Now he lives in a cluster of subsidized housing in Dorchester. The downward slide from his middle-class youth has been hard on him. “There’s people that are miserable here, and there’s a lot of drugs” — mostly heroin and crack.

The primary catch in his efforts to move to a calmer neighborhood has been the history that keeps popping up in the job application process. In one of his many attempts to land a solid position, Khalil made it to a second interview at a Whole Foods in 2016, but then, he said, they ran a background check and told him that, with his drug history, it was a no-go. He applied elsewhere, sometimes going to temp agencies, but nothing worked out long-term. He lost a job, then found work on the third shift at a warehouse, but couldn’t manage the schedule with his three kids. With Khalil unemployed, the family relied on his girlfriend working two jobs to hold things down.

“I wake up with the intention to pray so the rest of the day goes well. That is my life, somebody who commits his will to God as soon as he opens his eyes,” Khalil said. One of his prayers is to clear his record. Another: “I’ve been praying for years to find a job.”

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If you were stopped by the police in Massachusetts before 2008, when the state began incrementally decriminalizing possession, and you had a small amount of marijuana in your pocket or a single joint behind your ear, you could face an arrest, a fine, even jail time. The offense could become a permanent part of your record, hampering efforts to get a job, find housing, even access student loans. If you were stopped after December 2016, when the state fully legalized marijuana possession, you could flaunt a spliff in a cigarette holder and have an ounce of weed in your fanny pack, and you would face no charges, your job prospects would remain the same, and you could apply for housing or loans without the extra worry.

It’s this sense of arbitrariness that irks Khalil and others who believe expungement of marijuana convictions is a necessary step during the legalization process, and not just an afterthought. (At the federal level, any possession of marijuana remains punishable, at the first offense, by up to a $1,000 fine and a year in prison; it goes up from there. Federal prosecutions, however, became exceedingly rare after the Obama administration announced in 2013 it would no longer interfere with marijuana operations that followed state guidelines, and continue to plummet.)

The legal — some might call it ethical — discrepancy in Massachusetts wasn’t addressed by the state for nearly two more years, when the state passed an expungement statute in 2018, and lawmakers still didn’t make it easy. In fact, it’s been a mess.

In theory, someone like Khalil only needs to submit a petition to the court in order to have a conviction expunged. But in reality, they likely need to hire a lawyer or find one to work for free and present the case before a judge, typically with a stack of attending documents, evidence, a clear argument, and references. For some, convictions have already been sealed, under a previously established process that blocks some employers from seeing a past conviction, though police, prosecutors, and some state and all federal employers could still see it. Now, someone with a sealed record would have to get it unsealed, then petition to expunge.

Khalil has been trying to bleach his old rap sheet for more than a year. Even as courts began to reopen in late summer and early fall after being partially shut down due to Covid-19 restrictions, some courts were not processing expungements. “Access to expungement is not happening,” Pauline Quirion, Khalil’s attorney, told me, adding the old saw, “Justice delayed is justice denied.”

Clearing your name isn’t nearly as arduous in other states. Colorado Gov. Jared Polis, for example, recently pardoned nearly 3,000 people convicted of possession of up to two ounces of marijuana. If you’re eligible for a pardon in Colorado, the process is now automated; you just have to check a website to see if you’ve been cleared. Similar programs exist in California, Illinois, and Vermont. Other states offer the sealing of records — a half-measure, Quirion said.

As more of the population lives in states where marijuana is legalized, even celebrated, it is increasingly clear that ongoing punishment for having committed an act that is no longer a crime doesn’t square with current views on either justice or marijuana. A steady drumbeat for amelioration is gaining momentum, and in the calls for racial and social justice, expungement is at the forefront.

Sponsored by House Judiciary Chair Jerry Nadler (D-NY), with Kamala Harris as lead sponsor of the Senate companion bill, the MORE Act would remove cannabis from the Controlled Substances Act, push marijuana legalization into the federal realm, and include a funding mechanism incentivizing states to implement expungement programs. (At the same time, the World Health Organization is recommending that the United Nations’ Commission on Narcotic Drugs recognize the medical value of marijuana; the UN in December ended classification of the drug as having “particularly dangerous properties.”)

In New Jersey, whose legalization ballot measure is being closely watched as it could knock over the neighboring domino of New York — where the industry, currently only for medical use, is already a multibillion-dollar market — it took significant pressure from racial justice advocates to convince state legislators to include expungement provisions. The “virtual expungement” relief measure included in the state Senate version of the bill provides automatic annulment of past convictions. (The exception is for people seeking employment in the judicial branch, law enforcement, or the corrections industry. Similar bills have been approved by both the state Assembly and Senate, but are yet to be finalized.)

Rev. Charles Boyer, director of the New Jersey faith-based group Salvation and Social Justice, who had sought expungements as well as to make licenses to sell available to those previously penalized for selling marijuana, recently told Gothamist, “The [original New Jersey] ballot question leaves no room to do racial justice.” As reformers are learning, states that don’t work automatic expungement into legalization efforts, and only try to exculpate ex post facto, may run into Massachussetts’s expungement quagmire.

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Part of the difficulty of expunging a record in Massachusetts is technical, with the web portal to file a petition seemingly intentionally dysfunctional. When I tried to follow the steps, I was hit with a barrage of error messages, was ordered to download a new version of Acrobat Reader, and eventually funneled to the site “What to do if you can’t open court PDFs.” I toiled a few more minutes, and then, irked in that special way bureaucratic websites can irk you, felt like smoking something myself. “Even though it will look like the file isn’t there,” the page reads, “go ahead and save the file to your computer anyways.”

Massachusetts state Rep. Chynah Tyler (D), who has sponsored a state House bill focused on making marijuana expungements automatic (though it’s currently stalled), told me that one problem with the current law is that some of the state’s records are only kept on paper. So even an algorithm built to identify old marijuana violations in the system — one of the proposed components of her automatic expungement bill — might not work.

A seven-page, step-by-step pamphlet by Greater Boston Legal Services guides applicants through the current process: “My record carries a stigma, and that puts me at a disadvantage in applying for jobs, housing, or other opportunities,” the sample explanation reads. The pamphlet suggests providing supporting documents for why your record should be expunged and what other charges may be connected to the case, and reminds you to check the box to request a hearing.

“If your goal is to help people have a second chance and not be tied to the mistakes of their youth, then you need a better statute,” said Quirion, who is also director of CORI (Criminal Offender Record Information) of Greater Boston Legal Services.

There are also systemic obstacles to clearing your record. Because of the arcane, nearly Kafkaesque, difficulties to get the state to let you off the hook for what is no longer a crime in Massachusetts, you need a lawyer, which can cost hundreds of dollars or more. And if you’re looking for an expungement because the violation made it harder for you to get a job, you probably don’t have thousands of dollars lying around. One study, published in the Harvard Law Review and conducted in Michigan, found that people who received expungements saw their wages increase by an average of 25 percent within two years. Plus, the same racism driving the drug war that targeted and prosecuted the same people now seeking those expungements carries over into the broader economic sphere.

“We know that people in these communities are disproportionately impacted, they are still overpoliced, are still overincarcerated, and still have less access to health care” and economic opportunity, says Napoli, of the state marijuana advisory board. She pointed to the current chasmic economic inequality in parts of the state. As recently as 2017, a study found that the median net worth of white residents of Boston was just shy of $250,000. The median net worth of Black residents, meanwhile, was $8. When getting your record cleaned of something that is no longer a crime can mean hundreds or thousands of dollars in legal fees, wealth — or the poignant lack of it — matters.

According to the Massachusetts expungement law, it has to be in the “best interests of justice” for a judge to clear your record for a marijuana violation. Part of the problem is how that prerequisite is interpreted. Khalil first appeared in court with an attorney from Greater Boston Legal Services in August 2019. They made his case, and then waited until November, when the judge denied him: Clearing Khalil’s name was not, he ruled, in the best interests of justice.

That was as much explanation as they got. Quirion, who had taken over his case from another attorney, chalked it up to a philosophical stance some judges have. That philosophy is captured by John Carmichael, the police chief of a Boston suburb and another member of the state’s Cannabis Advisory Board, who told the Boston Globe in 2019, “It’s legal now — that doesn’t mean that 10 years ago, when they violated the law, that it shouldn’t become part of their record.”

Since Khalil’s denial, he has filed new motions and appeals. The next step of the appeals process was expected to move forward in November, and Khalil was hoping for a decision by the end of the year, but the process was delayed, again.

Throughout the slog — the year-plus of struggle to get his record expunged — he applied for yet another job, as a driver delivering fish and other products to grocery stores and restaurants in the Boston area. The first interview went well, and the manager signaled he’d be a great fit. A few days later, he got another call. They were sorry. “When they let me know,” Khalil said, “they said there were some things on my record that company policy won’t let us hire you for.”

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Expungements are one among many issues that regulators and the industry can focus on to work toward justice. Several people I spoke with noted the unique opportunity legalization has carved out for the country. “Because it’s not just about legalizing cannabis,” Napoli said. “We’re really creating a new industry. And we’re giving people opportunities that previously didn’t exist before. So, when you’re giving opportunity, you have to consider those who lost opportunity due to the prohibition of the same commodity.”

As Khalil put it: “I’m in a privileged position to see how it’s going to change for Black and brown people, people given the [short] end of the stick as far as the drug war is concerned.”

Horace Small, executive director of Boston’s Union of Minority Neighborhoods and a member of the “weed board,” as he dubbed the state’s Cannabis Advisory Board, told me, “We can create wealth, create jobs, and invest in our communities. This industry is going to last for generations.” But before the riches rain down, the state needs to do right by those they’ve wronged. It “rushed everything” when legalizing, Small explained. Equity was, at best, an afterthought.

According to a report from National Expungement Week — a coalition of organizations focused on offering services to communities affected by the war on drugs — nationally, only 4 to 6 percent of people eligible for their records to be expunged go forward with the process. And an investigation in Massachusetts found that of the 724 people who tried to expunge their marijuana violations in 2018, only 135, or less than 20 percent, were successful.

Even in the midst of a cultural and legal transformation of Americans’ relationship to cannabis, those seeking equity still have an uphill battle. (Even calling it cannabis is part of some marketers’ rebranding scheme, marking a difference between marijuana’s role in “wellness” and yuppie recreational usage and the drug that sent Khalil to prison.)

An ACLU report published in 2020 found that although the total number of marijuana arrests between 2010 and 2018 declined 18 percent from the previous eight-year period, there were still 6.1 million such arrests. (While some states have legalized controlled recreational use, it remains a crime in those states to sell the drug without a license.) In a Panglossian note, the ACLU report included the hope that its findings will be “the final nail in the coffin for the inane War on Marijuana.” But neither statistics nor science ever had much leverage with drug laws.

“Cannabis is one of those things that has just been in the hands of the people for so long,” explained Napoli, senior director of corporate social responsibility at Parallel, a cannabis company. The drug’s communal pull, its long human history, and its brutally racist political past also make the plant uniquely fit to lift up oppressed and targeted communities, she said.

In recompense for decades of a drug war that has torn apart communities, a newly legalized industry could — if it isn’t gobbled up by “Big Bud” operations, some of which are owned by tobacco, alcohol, and pharmaceutical giants — build wealth in those same communities.

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This fall, I visited one industry leader near Bryant Park in Manhattan: a sleek, Apple Store-styled medical marijuana dispensary run by MedMen. There were tables holding dozens of inlaid iPads touting their cannabinoid offerings, as well as a crew of pharmacists in the back and savvy associates up front to cater to specific woes. Though currently only attending to medical users (in California, Illinois, and Nevada, MedMen serves recreational customers as well), the store featured conspicuous peg holes in the walls aching for racks to flaunt a pharmacopeia of recreational weed-infused tinctures, chocolates, sprays, lotions, and Goldfish crackers. The whole store — really, the whole industry — seems built with the future in mind. But for some, it’s the past that needs reckoning with.

“We believe that if a state legalizes cannabis,” MedMen’s chief financial officer, Zeeshan Hyder, told me, “the state legislature should include expungement for former cannabis records and provide retroactive ameliorative relief.”

Khalil hopes for ameliorative relief, too. “I need a piece of that … I want some brick and mortar,” he said. Building toward a just society tomorrow must include taking on, and vitiating, past harms. Think of expungement — and marijuana reform more generally — as a step toward reparations.

Still struggling to find a job, Khalil instead found a fellowship program. Mass CultivatED — a brainchild of state lawmaker Chynah Tyler and a partially state-funded NGO — claims to be the first in the nation “jail-to-jobs” cannabis program. CultivatED begins with a paid, month-long course on the science and business of cannabis, followed by a month-long internship divided into two weeks in a grow house and two weeks in a dispensary.

In one of the early classes on the cannabis industry, Khalil and classmates watched videos of sophisticated farming operations and tony dispensaries run by what looked like well-heeled, green-thumbed techies. “These white dudes making millions of dollars. I’m tired of seeing those guys in those videos,” Khalil told me. “I want to be one of the guys making those videos.”

Denise Truscello/Getty Images for MedMen

Khalil and I spoke again a month into the fellowship, after his first day in the grow room. He had spent five hours clipping Red Vine Kush, a cannabis varietal. (“That shit was like aromatherapy.”) He was ready, he said, more amped than ever, to get into the industry: “I’ve seen pictures in the media, but it’s a totally different sandwich to touch it, to smell it.”

During a video tour of his apartment in early October, Khalil lit up a joint and took me outside. Leaving the apartment complex, he strolled by the small patch of grass where residents set up chairs in good weather, pointed out the halal chicken spot, a Dominican cafeteria, the single-family homes across the street. Besides the neighborly atmosphere, the bright sun, and the jaunty tour, the area is also known for overdoses, violence, and police harassment. The community is struggling, and Khalil is looking to get out, get ahead.

“People making millions of dollars in weed, and I still can’t get a job,” he repeated. That should change soon. He’s “very hopeful,” he said, that he’ll become a “beacon for people who’ve been disenfranchised by the drug war.”

At the end of the MassCultivatED program, fellows have a chance of being hired by one of the businesses. By the end of the year, in all likelihood, Khalil will be legally selling the same plant that sparked the criminalization and stigmatization that has hung over his life for the past 17 years, and, as his struggle to expunge drags on, hangs there still.

John Washington is a writer covering immigration and border politics, and criminal justice. His first book, The Dispossessed: A Story of Asylum at the US-Mexico Border and Beyond, was published in May 2020 by Verso Books.