Last night, John Oliver broke down how Obamacare was supposed to work and, five years after its passage, how how it actually works. While Obamacare was an undeniable victory for the left, it hasn’t been the Ryan Gosling marriage proposal dream-turned-reality we had been hoping for. In 2012, after multiple right wing legal challenges, the Supreme Court upheld “nearly all” of the Affordable Care Act, except for the provision that enabled the federal government to expand Medicaid to cover their low income uninsured — AND the federal government would cover 100% of the cost for the first 10 years and 90% of the cost thereafter. But 20 states — not surprisingly, the reddest of the red states, where governors could shore up Tea Party support and burnish a potential presidential candidacy with public displays of abject cruelty to the less fortunate — rejected the Medicaid expansion loudly and proudly, leaving approximately 3.1 million people in what has become known as the Medicaid Gap. On Tuesday, several states are holding elections for governors and statehouse legislators and the Medicaid expansion hangs in the balance, along with millions and millions of uninsured. Mississippi is one of those states. Ol’ Miss resident Lashombee Hoard, is one of those languishing in the Medicaid gap. She tells a Last Week Tonight film crew she can’t afford Obamacare, makes too much money to qualify for Medicaid and can’t afford her company’s health insurance. “I’m just hanging in the air,” she said on the verge of tears, explaining how she re-uses needles to save money. Oliver summed up the issue with a male wardrobe malfunction simile, “Health care is like a pair of gym shorts, even if it covers nearly all of what it’s supposed to you are still left with some problematic gaps and terrible things can happen.” — MEGAN MATUZAK