By the time the maker of OxyContin pleaded guilty to a federal charge of misbranding the drug in 2007, Purdue Pharma had spent a decade selling opioid prescriptions through commercial health plans. Five years later, with restrictions tied to the plea deal expiring, Purdue saw a new sales opportunity in an "aging population with painful conditions," according to internal company documents. As the U.S. opioid crisis deepened, records show, Purdue sharpened its focus on the federal government’s Medicare prescription program for seniors. Between 2012 and 2013, Purdue deployed an email marketing campaign to healthcare providers, launched new advertising in a long-term-care medical journal, and armed its sales force with patient vignettes to share with doctors. Each effort emphasized OxyContin’s insurance coverage through what’s known as Medicare Part D. "Medicare Part D is the only significant and growing book of business for OxyContin," a McKinsey analysis for Purdue found in 2013. Telling doctors the opioid was covered by Medicare was only one part of the equation. To secure that coverage, Purdue had to negotiate terms with two corporate giants in the Medicare business, UnitedHealth Group and CVS Health. A Barron's investigation—the second in a series on pharmacy-benefit managers, or PBMs—found that Medicare coverage administered by arms of UnitedHealth was a top source of OxyContin sales, at a time when government watchdogs were raising alarms about opioid use and spending in the program. UnitedHealth and CVS wear multiple hats in Medicare Part D. They serve as so-called sponsors of drug plans that seniors can purchase each year. They also operate PBMs, the middlemen that negotiate between drugmakers and insurance companies.