On his last night as a free man, Dan Muessig, the internet-famous ex–criminal defense attorney and former pot king of Squirrel Hill, did nothing in particular. By that point, he told me, he wasn’t up to it. He had already shared the melancholy seven-course Italian last supper with family and friends several weeks prior, already bid farewell to his elderly parents, already gazed at the quotidian set dressing of daily life (familiar faces, foliage, streets) and longed for it all even in its presence. There had already been time for misery and regret, and there would be more time for it yet. But as the hours between Muessig and May 11, 2022—the date he would surrender himself into federal custody for a prison term of five years as punishment for selling marijuana—passed, he was still. He sat by his wife on their couch, he said, and thought of the years that would stretch onward before he could touch her again.
Muessig had appeared ashen and weary during our May 7 Zoom conversation several days earlier, with bleak desperation where so much rakish juvenile delinquency had once been. Mauve shadows ringed his eyes. He laughed low, faint, and spare. He is no longer a lawyer and no longer a drug dealer; now his business is real estate. Muessig was never accused of, indicted for, or convicted of committing any sort of violence—but if his youthful mien had once registered as vaguely menacing nevertheless, nothing about him does now. He speaks more softly these days, and he doesn’t say much that could register the degree of offense that federal prosecutors, among so many others, evidently took when he dropped a semi-infamous viral video ad back in 2014—but we’ll get to that. For now, it’s enough to say that Muessig has gotten older over the past couple of years, like all of us but worse.
Not that any of this will convince a certain kind of critic, who sees in Muessig not much more than an affluent Millennial drug dealer who left a legal career behind to return to his (much more lucrative) profession of choice. Muessig doesn’t disagree. He pleaded guilty; he admits he broke the law. But the laws themselves are weak, confused, and shifting, and the penalties absurd in light of marijuana’s widespread and growing legality. Muessig may be a punk, and you don’t have to like him, but even by the standards laid out by a campaign-trail Joe Biden, a onetime champion of the War on Drugs, he shouldn’t be in prison.
In that sense, the president is just keeping up with the times. The inability of anyone—Richard Nixon, Nancy Reagan, Billy Graham—to give an objective account of why marijuana, unlike other risky but broadly legal recreational substances such as alcohol and cigarettes, ought to be subject to special prohibition has slowly eroded America’s anti-cannabis legal architecture. To date, 18 states as well as the District of Columbia have legalized marijuana for adult recreational use; meanwhile, 37 states plus the capital have also enacted laws permitting doctors to prescribe marijuana to their patients. Even states that ban recreational and medical marijuana use allow the medical use of cannabidiol, a chemical compound derived from the very same cannabis plant that, processed in a different fashion, can be dried, ground, rolled, and smoked. For millions of marijuana users, buying weed is an ordinary ID-flash transaction, no different from stopping at the liquor store—and yet these fragments of prohibition remain, such that the past and future seem to have arrived at once, while a fair present is still missing.
[Read: The superiority of a states’ rights approach to marijuana]
Politicians and litigators have struggled to manage the weird crises produced by these sudden shifts in marijuana policy. In California, for instance, a measure enacted with the state’s 2016 legalization statute promised a pathway to clear past marijuana convictions, but as of 2022, thousands of people were still waiting for their records to resolve. States where possession is legal have found themselves in conflict with federal authorities: No sooner had California passed legalization than Donald Trump’s first attorney general, Jeff Sessions, rescinded the “Cole memo,” an Obama-era directive that had promised state attorneys general limited discretion to legalize marijuana with reasonable regulation without much fear of federal interference. Sessions went on to issue a scathing memo on marijuana enforcement to U.S. attorneys in 2018, stating that “the previous issuance of guidance undermines the rule of law” and demanding that prosecutors “use previously established prosecutorial principles that provide them all the necessary tools to disrupt criminal organizations, tackle the growing drug crisis, and thwart violent crime across our country.”
In theory, the administration of Joe Biden was going to ease the growing tension between federal and state marijuana policies by essentially ending federal enforcement of marijuana prohibition, if not enacting federal decriminalization measures. On the campaign trail, then-candidate Biden said, among other things, that for nonviolent marijuana-related crimes it “makes no sense for people to go to jail,” and that “we should decriminalize marijuana, period, and I think anyone who has a record should be let out of jail, their records expunged—be completely zeroed out.” But Biden has not kept his promises. Almost 3,000 federal prisoners remain behind bars on marijuana charges, though Biden’s then–press secretary Jen Psaki told reporters on April 20 that the president “remains committed” to exercising the clemency he hasn’t yet shown.
[Read: The marijuana superweapon Biden refuses to use]
In the meantime, Dan Muessig can do little more than wait, and reflect on how everything fell apart the way it did. When we talked over Zoom and text in the days leading up to his incarceration, all his thoughts seemed to loop back to that damned viral video ad from 2014.
“I didn’t make the commercial as a way of aggrandizing my criminality,” Muessig told me, apropos almost of nothing, as though I might have suspected he had. Years ago, in 2014, fresh out of law school and looking to build a client base, the then–trim and energetic young lawyer (who had, perhaps unlike most of the fine men and women who matriculate through the University of Pittsburgh Law School, spent several years touring internationally, if not glamorously, as an underground rap artist by the name of Dos-Noun) released a tongue-in-cheek video advertisement for his criminal-defense services. In the three-and-a-half-minute ad, Muessig is young and wolfish, pitching his services to potential clients with glib efficiency: “America was built on freedom,” he cajoles at one point, “not on a bunch of people with more money than you telling you what you can and can’t do with all their stupid laws.” Meanwhile, friends of Muessig’s—portraying criminals in the act—thank their lawyer friend (“Did I mention I’m Jewish?” Muessig teases at one point, spinning a dreidel invitingly) for his services, and go right on committing their crimes.
Muessig’s peers, colleagues, and superiors in the Pittsburgh criminal-justice system were not amused. “Oh my God. It was like a fucking pack of vipers,” he recalled in an interview with HipHopDX last month. “Prosecutors professionally don’t have a sense of humor. Judges too, you know?”
At the time, Muessig was somewhat tickled by the backlash. He enjoyed a moment of countercultural notoriety, chatting casually with Vice about Pittsburgh rap and confidently telling Esquire that he was glad to be typecast as a mischievous sleaze: “I’m a streetwise Jewish kid who grew up in the city and transitioned from someone who was a hip hop head to a successful criminal attorney. I created this pigeonhole in order to get to it. I embrace it.”
But embracing legal work full-time turned out to require much more discipline and sternness of constitution than Muessig could muster. Fundamentally, he was a weed guy, not a law guy—friendly, sociable, and a better fit with the offbeat and bohemian elements in society than the straightlaced and professional. Though he had dealt a little weed in law school, he told me, he escalated operations as his legal practice began to feel unrewarding and overwhelming, with constant requests to do free work for family and friends, blatant disrespect from prosecutors and colleagues based on the provocative ad, and relatively little pay compared with the income from his growing pot business. Eventually, he decided to move into full-time selling. “I wasn’t an amazing lawyer or anything like that,” Muessig said. And with his reputation, he struggled to help his clients as much as he would have liked to. His mere presence had become a hindrance.
The Pittsburgh pot market, meanwhile, was red-hot, despite (or perhaps, in part, thanks to) Pennsylvania’s ban on recreational marijuana. Working with a few friends, Muessig opened up what effectively became an underground dispensary. Muessig and his employees eventually turned the shop into a full-fledged retail operation complete with register shifts, security, regular pricing, and, yes, advertising: “The store,” as it came to be known to its adoring customers, proudly invited customers to call anytime at 412-543-TREE.
While friends operated the store, Muessig moved up in Pittsburgh’s weed supply chain, shepherding more and more of the city’s marijuana inflows as time went on. By 2019, Muessig told me, he and his employees had established “a completely separate wholesale operation.” Muessig was regularly purchasing hundreds of kilograms of marijuana for hundreds of thousands of dollars and moving the product through the city for even greater profit, making him the undisputed weed kingpin of the Pittsburgh metro area. Along with the street cred and camaraderie Muessig had been looking for, his new work brought in a substantial amount of money, which came with its own risks. “Now you’re locked in,” he told me, reflecting on the influx of cash that came his way shortly before the fall. “You’ve spent years working towards this, even when you told yourself maybe that you weren’t going to do this or whatever. Now you’re up top, now you’re the big dog, everyone calls you ‘boss.’” Many people, some with dependent families, now relied on him for their regular income. The stakes had suddenly become very high.
[From the January/February 2019 issue: Ending weed prohibition hasn’t stopped drug crimes]
Federal prosecutors would later reveal in Muessig’s sentencing memorandum that investigators from the Federal Bureau of Investigation and the Greater Pittsburgh Safe Streets Task Force obtained nine wiretap-authorization warrants from January to May of 2019 as they jointly worked to bust a group of Pittsburgh criminals known as the SCO gang. SCO, whose membership operated out of the Braddock neighborhood, dealt mainly in heroin and cocaine, which had initially attracted federal attention; their marijuana sales, which ultimately led to Muessig’s indictment, seemed to be something of an afterthought. But Muessig was the wholesale supplier for the city at the time, and SCO’s weed delegate was regularly purchasing product from one of his employees. That’s the nature of a monopoly, and it’s the hard truth the feds laid out in their 12-page memo, which, despite alleging no particular harm or injury to any person caused by Muessig, still calls for the man to spend years behind bars. In March of this year, a judge sentenced Muessig to the five-year mandatory-minimum sentence for conspiracy to distribute marijuana and possession of marijuana with intent to sell, charges he’d pleaded guilty to in November 2019.
And so the feds got their wish. Of course, they may have been just as satisfied regardless of the specific sentence. No victims are mentioned in the sentencing memo; the only effort to link Muessig with any harm comes in the form of the argument that by supplying marijuana to a gang primarily selling harder, more dangerous drugs, Muessig had strengthened the gang’s hand. What does come up—over and over again—is Muessig’s 2014 viral ad. In fact, the memo takes as an epigraph a line spoken by Muessig in the ad—“Consequences, they sure suck, don’t they?”—as though to taunt the man that his punishment has indeed arrived.
I hope that Dan Muessig comes home—soon. But American marijuana policy has already changed what home is and will be. Muessig doesn’t smoke weed anymore, he said, though he misses it sometimes. But the pleasure is gone. One of Muessig’s original marijuana-business partners died in 2017, running drunk through traffic after a girlfriend. When the indictments came down, one of Dan’s close friends and associates, a 62-year-old grandfather, committed suicide; he didn’t want to go to prison or inform on anyone else, Muessig explained, heartbroken, in a subsequent pre-prison interview. (Muessig, for that matter, also refused to testify against any member of his or any other operation for federal investigators.) The man’s son, also a longtime friend of Muessig’s, overdosed and died. Muessig and his wife had begun adoption proceedings before they were made aware that he would be doing prison time, and of course all of that fell through right away. Muessig’s mother is ailing, and he worries he will not see her again.
Now, he wrote to me by prison email recently, he thinks of the women in his life constantly, and aches. “This is a sad, sad place,” Muessig’s note read. “Not dangerous in the physical sense, but as corrosive mentally as any place I’ve ever imagined, let alone lived in … I miss [my wife] and my mom with more force than I previously thought possible.”
When Muessig returns, he will presumably return to the work he left behind: real estate. Buying weed used to be the kind of thing you needed a guy like Muessig for. But those days are waning. Marijuana is still illegal in Pennsylvania, but the state now looks like a holdout, as neighboring states including Maryland, New York, and New Jersey have legalized or decriminalized pot. Across the country, one can purchase weed as impersonally as anything else now, and why not? Whatever romance there once was is fading, as the mundane contours of the retail experience—waiting in line, mumbling selections from a menu, fiddling with an ATM—null the mystique. In that sense, Muessig is like Steve McQueen’s Tom Horn, an old cowboy who outlived the frontier. Society had a practical use for him in the past, and a romantic legacy for him in the future, but no place for him in the time he lived.