The drug at the center of it all was sixty-two years old and cost about a dollar a pill to make. Daraprim — pyrimethamine — was approved in 1953 and had long been the standard treatment for toxoplasmosis, a parasitic infection that kills people whose immune systems have been wrecked by AIDS, chemotherapy, or organ transplantation. It had no patent protection worth mentioning; what it had, by 2015, was a market so small — a few thousand American patients a year — that no generic manufacturer had bothered to compete for it. In August of that year, a thirty-two-year-old former hedge-fund manager named Martin Shkreli bought the drug’s U.S. rights for his startup, Turing Pharmaceuticals, and raised the price overnight from $13.50 a pill to $750 — an increase of more than five thousand per cent — while locking the drug inside a closed distribution system carefully engineered to prevent would-be generic rivals from obtaining the samples they needed to enter the market. When the New York Times reported the increase that September, Shkreli did not do what cornered executives do. He did not apologize, resign, or hide. He went on television and defended the price as capitalism functioning correctly, quoted rap lyrics at his critics on Twitter, and visibly, unmistakably, enjoyed himself. Within a week he had acquired the title that followed him through two trials, seven years of litigation, and one lifetime ban: the most hated man in America.

The Price

The Daraprim increase was not, as Shkreli’s critics sometimes carelessly claimed, a death sentence administered by spreadsheet; the company maintained patient-assistance programs and argued, with some technical accuracy, that most patients’ out-of-pocket costs were buffered by insurance. What the price did was tax the system itself — hospitals, insurers, public programs — and, more dangerously for patients, disrupt the supply chain: infectious-disease physicians reported treatment delays as hospitals dropped the drug from formularies and scrambled through the restricted distribution network, and professional societies for H.I.V. medicine and infectious disease wrote formally to Turing that the pricing was unsustainable and unjust for a sixty-two-year-old standard of care. Presidential candidates in both parties denounced him within days — a unanimity of political contempt achieved by almost no other figure of the decade — and the biotech industry’s own trade association took the extraordinary step of publicly disowning Turing, less, cynics observed, from moral injury than from terror at what the spectacle would do to the sector’s pricing latitude. They were right to be terrified. Congressional investigations into drug pricing multiplied, and every subsequent pricing controversy — insulin, EpiPen, the rest — was prosecuted in public with Shkreli’s face as its shorthand.

The Prodigy

The biography beneath the persona was, in its early chapters, the immigrant striver’s tale America claims to prefer. Shkreli was born in 1983 in Brooklyn to Albanian and Croatian immigrant parents who worked as janitors; he was bright, restless, obsessive about markets, and by his late teens had talked his way into an internship at Cramer, Berkowitz, the hedge fund co-founded by the television stock-picker Jim Cramer, where his precocious short-selling recommendations reportedly drew a regulatory inquiry that went nowhere. In his twenties he launched hedge funds of escalating ambition and identical trajectory: Elea Capital, which died in 2007 after a catastrophic trade with Lehman Brothers; then MSMB Capital, whose specialty was shorting biotech companies Shkreli would savage — often perceptively — in online postings. In February 2011, MSMB made a disastrous naked short bet against a drug company through Merrill Lynch and was effectively wiped out, losing more than seven million dollars it did not have. And here the story forked away from ordinary failure, because Shkreli did not tell his investors they had been wiped out. He sent them statements showing gains. For years afterward, the government would prove, he reported steady returns on funds that were functionally dead — while founding a new vehicle, a biotech startup called Retrophin, whose assets he eventually raided to make his defrauded fund investors whole.

That sentence contains the entire peculiarity of the criminal case against Martin Shkreli, and it is worth pausing on. The investors in MSMB — sophisticated, wealthy people who had been lied to comprehensively for years — ultimately got their money back, and then some, in cash and Retrophin stock that appreciated handsomely. At trial his lawyer, Benjamin Brafman, built the defense on precisely that arithmetic: whatever Shkreli had said, no one ended up poorer. The government’s answer, which the law has always given, is that fraud is the lie, not the loss — that an investor deceived about where his money is and what it is doing has been robbed of the decision, whatever the eventual balance. The jury in Brooklyn split the difference with some care: in August 2017, after a trial in which the judge had to excuse scores of potential jurors for volunteering their loathing of the defendant, it convicted Shkreli on two counts of securities fraud and one of conspiracy — the counts tied to lying to his fund investors — and acquitted him on five others, including the charge that he had looted Retrophin. Shkreli called the verdict a vindication and went home to stream himself playing video games.

The Performance

Between indictment and sentencing, Shkreli conducted what may be the most self-destructive publicity campaign in the history of the federal docket. The template had been set in February 2016, when he appeared under subpoena before a House committee investigating drug prices and declined, on advice of counsel, to answer questions — which the Fifth Amendment entitled him to do — while smirking, eye-rolling, and generally performing contempt for the assembled legislators, then tweeting, minutes after leaving the room, that they were “imbeciles.” He had already purchased, for two million dollars, the sole copy of the Wu-Tang Clan album Once Upon a Time in Shaolin, less as music than as the world’s most expensive troll. Out on bail after his conviction, he offered his Facebook followers five thousand dollars to grab a strand of Hillary Clinton’s hair during her book tour; Judge Kiyo Matsumoto, unamused by the defense’s characterization of the post as satire, revoked his bail in September 2017 and sent him to await sentencing in the Metropolitan Detention Center. In March 2018, after finding — crucially — that the intended loss from his frauds exceeded ten million dollars regardless of eventual repayment, she sentenced him to seven years and ordered forfeiture of $7.36 million in assets, the Wu-Tang album among them. Shkreli, who had faced the courtroom with theatrical composure for two years, wept as he asked for leniency. The federal government later sold the album to a cryptocurrency collective, a disposition so perfectly of its era that no novelist would dare invent it.

The weeks around his indictment supplied a coda so strange it is often forgotten. In November 2015, Shkreli led a group that bought control of KaloBios Pharmaceuticals, a failing biotech whose stock had been left for dead; the announcement of his involvement sent the shares up more than a thousand per cent in days, a monument to the era’s meme-stock physics assembled around a man not yet charged. On December 17, 2015, F.B.I. agents arrested him at his Manhattan apartment before dawn; KaloBios fired him within days and was in bankruptcy within weeks, its brief resurrection and collapse tracking nothing but the persona itself. Retrophin, the company he had founded and been expelled from, pursued him separately, suing for sixty-five million dollars over the settlement agreements — the very transactions at the heart of the criminal case — in which defrauded MSMB investors had been quieted with Retrophin’s cash and stock. The board’s complaint described a chief executive who treated a public company as his personal checkbook; Shkreli described a board of ingrates seizing what he had built. Both descriptions fit the record, which has always been the difficulty with him: the self-dealing and the value creation were the same transactions viewed in different light.

The Ban

The criminal case never touched Daraprim; raising a drug’s price fifty-fold is not, in itself, a federal crime. But the price hike had a legal vulnerability buried in its mechanics, and the Federal Trade Commission, joined by New York and six other states, spent years excavating it. The 2020 lawsuit did not claim the price was too high; antitrust law is indifferent to gouging as such. It claimed that Turing — by then renamed Vyera — had built an illegal fortress around the monopoly: exclusive supply deals locking up the world’s manufacturers of the active ingredient, distribution contracts drafted to keep Daraprim out of the wholesale channels from which generic firms buy the samples the F.D.A. requires for approval, and data-blocking provisions to hide sales figures from competitors’ market analysts. The scheme worked for years — the samples were the chokepoint, and Shkreli had, in internal communications the court found explicit, designed it that way. In January 2022, after a bench trial, Judge Denise Cote of the Southern District of New York issued a hundred-and-thirty-page opinion concluding that Shkreli — who had continued directing company strategy from prison on a contraband cell phone — was the architect of an anticompetitive scheme, ordered him to disgorge up to $64.6 million, and imposed the remedy that made the case a landmark: a lifetime ban on participating in the pharmaceutical industry in any capacity. Banishment for life from an entire lawful industry is an extraordinary remedy, and Cote justified it in terms courts usually reserve for recidivist racketeers: Shkreli’s conduct was “flagrant,” his contrition nonexistent, and nothing short of exile would protect the public. In January 2024 the Second Circuit affirmed the ban in full.

The Sideshows

Prison did not interrupt the performance so much as relocate it. From FCI Fort Dix in New Jersey, Shkreli ran his commentary operation through the contraband phone that Judge Cote’s antitrust opinion would later make legally consequential — posting under aliases, dispensing stock takes, and, according to the government’s filings in the F.T.C. case, continuing to direct Vyera’s affairs from his bunk. The outside world reciprocated with the strangest subplot of the saga: in December 2020, Christie Smythe, the Bloomberg News reporter who had broken the story of his 2015 arrest, revealed in an Elle magazine profile that she had quit her job, left her marriage, and fallen in love with him during years of prison visits and calls — a disclosure that ignited a round of journalism-ethics symposia and that Shkreli, characteristically, met with a shrug relayed through a spokesman wishing her well. The federal government, meanwhile, liquidated his trophies: in 2021 the Justice Department sold Once Upon a Time in Shaolin to PleasrDAO, a cryptocurrency collective, for four million dollars, applying the proceeds to his forfeiture judgment — the one-of-one album passing from the most hated man in America to a decentralized autonomous organization, a chain of custody that functions as a core sample of the decade.

Release, in 2022, restored him to the only industries not closed to him: attention and crypto. He launched a Web3 drug-discovery venture called Druglike — a name selected, one assumes, for maximum proximity to the boundary of the lifetime ban without formal crossing — and a joke token bearing his name whose value chart performed the full Shkreli arc in miniature. Regulators and plaintiffs have circled these ventures continuously, and the F.T.C. has shown itself willing to police the ban’s perimeter. He streams; he opines; he is periodically deposed. The persona, tested against every institution American law could throw at it — a jury, a judge, the Bureau of Prisons, an appellate court, a lifetime injunction — emerged not merely intact but load-bearing: it is, at this point, his sole remaining asset, and it appreciates with each new proceeding.

The Experiment

Shkreli walked out of federal custody in May 2022, released early to a halfway house, and resumed the only career left to him, which is being Martin Shkreli — podcasts, livestreams, contrarian stock commentary, flirtations with crypto ventures that promptly drew regulatory attention. The persona survived intact because the persona was never punished; the law reached his lies and his monopoly plumbing, not his affect. And that is precisely what makes his case the most legible ethics document of its decade. The public wanted Shkreli punished for Daraprim — for the sneer, the hearing, the five-thousand-per-cent assertion that a dying patient’s desperation is just inelastic demand. The system could not do that, because nearly everything abhorrent about the Daraprim play was legal, and remains so: no federal statute then or now caps the launch price of an off-patent drug, and the closed-distribution maneuver was punished only because it crossed into antitrust conspiracy, years later, after extraordinary litigation effort. So the system did what systems do — it found the charges it could prove. He went to prison for defrauding millionaires who lost nothing, while the act that actually endangered lives cost him, in the end, money and a ban.

The trial had, in fact, staged the era’s clearest confrontation between the two Shkrelis. The prosecution’s witnesses were his own investors — hedge-fund allocators, physicians, a banking heir — who testified, with evident discomfort, that yes, they had been lied to about audits that did not exist, brokers who were never engaged, assets under management inflated by an order of magnitude; and yes, they had ultimately received their money back multiplied. One investor conceded on cross-examination that his dealings with the defendant had been, in the end, the best investment he had ever made. Brafman’s summation invited the jury to treat that as absolution; the prosecutors, in theirs, asked the question the verdict answered: whether a man who lies to get the money, lies to keep it, and manufactures the eventual repayment out of a third company’s assets has committed no crime merely because his luck held. Three counts said the lies were the crime. The luck was never on trial.

It is customary to call this hypocrisy, but it is closer to an honest confession of what law is for. Criminal law protects the integrity of specific promises — the account statement, the audit, the market’s plumbing — because those are what legislatures have chosen to protect; the broader outrage, that a man could tax the dying and call it fiduciary duty, was referred to the legislature that created the conditions and has largely declined to change them. Drug-pricing reform advanced only incrementally in the years after Turing, and the specific playbook — acquire a neglected off-patent drug, raise the price, restrict the samples — was run by quieter men before and after Shkreli, men who did not tweet, were not hated, and were not sued. His true offense against the industry, colleagues in pharma complained at the time, was saying the quiet part at full volume with cameras on. The others got price increases; he got the ban. Somewhere in that arithmetic is the lesson the case actually teaches: American professional life forgives a great deal of harm if it is administered with decorum, and punishes indecorum with the whole weight it declines to apply to the harm. Shkreli, who understood markets better than manners, priced everything correctly except the smirk.