The lunch rush at Tom’s on Main in Yazoo City had come to a close, and the waitresses, after clearing away plates of shrimp and cheese grits, seasoned turnip greens and pitchers of sweet tea, were retreating to the counter to cash out and count their tips. Wylene Gary was at the register ringing up the last of the $6.95 lunchtime specials as we chatted about her job, a modest low-paying one of the sort all too common in Mississippi, America’s most down-and-out state, where a full 20 percent of the population doesn’t graduate from high school, 22 percent lives in poverty—and even more than that, a quarter of the state, goes without health care coverage.

Gary didn’t have health insurance either, not that she hadn’t tried. When the Affordable Care Act mandated that Americans buy coverage, she didn’t want to be a lawbreaker: She had gone online to the federal government’s new website, signed up and paid her first monthly premium of $129. But when her new insurance card arrived in the mail, she was flabbergasted.

“It said $6,000 deductible and 40 percent co-pay,” Gary told me, her timid drawl giving way to strident dismay. Confused, she called to speak to a representative for the insurer Magnolia Health. “‘You tellin’ me if I get a hospital bill for $100,000, I gotta pay $40,000?’” Gary recounted. “And she said, ‘Yes, ma’am.’”

Never mind that the Magnolia worker was wrong—Gary’s out-of-pocket costs were legally capped at $6,300. She figured that with a hospital bill that high, she would have to file bankruptcy anyway. So really, she thought, what was the point?

“This ain’t worth a tooth,” she said.

She canceled her coverage.

***

The first year of the Affordable Care Act was, by almost every measure, an unmitigated disaster in Mississippi. In a state stricken by diabetes, heart disease, obesity and the highest mortality rate in the nation, President Barack Obama’s landmark health care law has barely registered, leaving the country’s poorest and most segregated state trapped in a severe and intractable health care crisis.

“There are wide swaths of Mississippi where the Affordable Care Act is not a reality,” Conner Reeves, who led Obamacare enrollment at the University of Mississippi Medical Center, told me when we met in the state capital of Jackson. Of the nearly 300,000 people who could have gained coverage in Mississippi in the first year of enrollment, just 61,494—some 20 percent—did so. When all was said and done, Mississippi would be the only state in the union where the percentage of uninsured residents has gone up, not down.

Why has the law been such a flop in a state that had so much to gain from it? When I traveled across Mississippi this summer, from Delta towns to the Tennessee border to the Piney Woods to the Gulf Coast, what I found was a series of cascading problems: bumbling errors and misinformation; ignorance and disorganization; a haunting racial divide; and, above all, the unyielding ideological imperative of conservative politics. This, I found, was a story about the Tea Party and its influence over a state Republican Party in transition, where a public feud between Governor Phil Bryant and the elected insurance commissioner forced the state to shut down its own insurance marketplace, even as the Obama administration in Washington refused to step into the fray. By the time the federal government offered the required coverage on its balky HealthCare.gov website, 70 percent of Mississippians confessed they knew almost nothing about it. “We would talk to people who say, ‘I don’t want anything about Obamacare. I want the Affordable Care Act,’” remembered Tineciaa Harris, one of the so-called navigators trained to help Mississippians sign up for health care. “And we’d have to explain to them that it’s the same thing.”

Even the law’s vaunted Medicaid expansion, meant to assist those too poor to qualify for subsidized private insurance, was no help after the U.S. Supreme Court ruled that states could opt out. Bryant made it clear Mississippi would not participate, leaving 138,000 low-income residents, the majority of whom are black, with no insurance options at all. And while the politics of Obamacare became increasingly toxic, the state’s already financially strapped rural hospitals faced a new crisis from the law’s failure to take hold: They had been banking on newly insured patients to replace the federal support for hospitals serving the uninsured, which was set to taper off as people gained coverage. Now, instead of more people getting more care in Mississippi, in many cases, they would get less.

“We work hard at being last,” said Roy Mitchell, the beleaguered executive director of the Mississippi Health Advocacy Program, when we met in Jackson. “Even a dog knows the difference between being tripped over and being kicked.”

In fact, it’s hard to find a list where Mississippi doesn’t rank last: Life expectancy. Per capita income. Children’s literacy. “Mississippi’s people do not fare well,” wrote Willie Morris, a seventh-generation native son who grew up in Yazoo City, once a bustling trading center perched on the southern edge of the cotton-rich Delta. Today, nearly half of Yazoo City’s residents live in poverty; its people, like the Delta’s vast swamps, have largely been drained away, along with the farming and factory jobs that used to support them. In a state with a population that is still half rural, signs of impoverishment are everywhere: irrepressible kudzu vines pressing into the glass door of an abandoned building; tipsy wooden shacks that look neglected and forlorn are instead occupied with life. “The Depression, in fact, was not a noticeable phenomenon in the poorest state in the Union,” Eudora Welty wrote of Mississippi in the 1930s. It remains the poorest state today.

None of which bodes well for health coverage in Mississippi. Small businesses that dominate the economy typically don’t offer health insurance, and Mississippi’s public health program for the poor is one of the most restrictive in the nation. Able-bodied adults without dependent children can’t sign up for Medicaid in Mississippi, no matter how little they earn, and only parents who earn less than 23 percent of the federal poverty level—some $384 a month for a family of three—can enroll. As a result, one in four adult Mississippians goes without health coverage. For African-Americans, the numbers are even worse: One in three adults is uninsured.

It is difficult to untangle the state’s dismal health from its past. For African-Americans, even going to a doctor can be a fraught historical act in Mississippi. There are the practical reasons that come from being poor and uninsured, but there is also a toxic legacy: the Jim Crow laws of living memory that barred blacks from most doctors’ offices, the widespread practice of sterilizing black women as a form of birth control, a practice so common it became known as “Mississippi appendectomies.” Perhaps it’s no surprise then that Mississippians today are less likely than the rest of the country to seek primary care for chronic conditions and more likely to turn to hospitals when those ailments become more serious and expensive.

Gruesome ends await.

Mississippi has the highest rate of leg amputations in America and one of the lowest rates of hemoglobin H1c testing, used to monitor and prevent diabetes complications. Amputations on African-Americans are even more startling: 4.41 per 1,000 Medicare enrollees versus 0.92 for non-blacks. The state also has high breast cancer death rates, even though it has low breast cancer incidence rates. The cancer often isn’t detected until it’s too late.

***

Mississippians are all too familiar with the dirge of bleak statistics. During my travels, I often heard, “We know what the rest of the country thinks of us.” It would become a point of pride, then, that in 2007, Mississippi actually appeared to be leading a health race it wanted to win. That fall, a full year before Obama’s election to the White House put national health care reform on the agenda, the governor, Haley Barbour, called up the newly elected state insurance commissioner, Mike Chaney, a Vietnam vet from Vicksburg. The two Republicans had been friends since college; Chaney had been the rush chairman for Sigma Alpha Epsilon at Mississippi State University when Barbour pledged the fraternity. Now, the governor had an assignment for his old friend.

“He said, ‘Chaney, I want you to get involved in something that the Heritage Foundation had talked about,’” Chaney, 70, recalled when I spoke to him at his Jackson office in June. Barbour, a folksy titan who had returned to rule over Mississippi politics after a successful career as a Washington superlobbyist and national Republican Party chairman, had enraged advocates for the poor with a series of stringent new restrictions on Medicaid.