He Earns Too Much for Medicaid and Too Little for His Prescriptions — One Year From Medicare, Curtis Kessler Is Just Waiting

Roughly 3.3 million Americans between ages 60 and 64 are either uninsured or enrolled in plans that leave significant medical costs uncovered, according to estimates from the KFF health policy research organization. Many of them are, like Curtis Kessler, simply counting down the months until they turn 65.

I met Curtis on a Tuesday morning in late February 2026, at a free tax preparation clinic held inside a public library branch on Chicago’s Northwest Side. He was sitting in a plastic chair, holding a manila folder stuffed with 1099 forms, waiting for a volunteer preparer. He wore a gray fleece and the kind of expression that suggests a person has already rehearsed whatever bad news is coming.

Curtis is 64, a licensed real estate agent who has worked independently for nearly eighteen years. He is single, lives with a roommate to split costs on a two-bedroom apartment, and has no dependents. When I introduced myself and explained what I was working on, he gave a short laugh. “You want to hear about someone who should have figured this out by now,” he said. “Sure. Pull up a chair.”

A Good Year That Made Things Worse

Curtis’s situation did not begin as a crisis. For most of his career, he earned somewhere between $48,000 and $62,000 annually — enough to qualify for meaningful subsidies on Illinois’s ACA marketplace, Get Covered Illinois. His monthly premium after subsidies ran around $210, and his plan included a formulary that covered both of his maintenance prescriptions — metformin for Type 2 diabetes and lisinopril for blood pressure — at a $15 copay each.

Then 2024 happened to be a genuinely strong year for Chicago real estate. Curtis closed more transactions than usual and landed a few commercial referrals that padded his income. When he filed his 2024 taxes, his adjusted gross income landed at $79,400.

That income bump triggered a reconciliation on his taxes — he owed back a portion of the premium tax credits he had received during 2024. But the longer-lasting consequence was what happened to his 2025 marketplace plan. When he went to re-enroll, his estimated income for 2025 pushed him into a bracket where his subsidized premium more than doubled, and the only plan he could reasonably afford came with a $6,800 deductible and a drug formulary that placed both of his prescriptions in Tier 3.

“I made more money one year and it cost me,” Curtis told me. “I know how that sounds. But I’m not a wealthy man. I’m a guy who had a lucky streak, and now I’m paying for it.”

The Prescription Problem Nobody Warned Him About

Under his new plan, metformin — available as a generic — costs Curtis $28 a month. That is manageable. The problem is lisinopril, which his new insurer placed in a tier that charges him $156 per fill for a 30-day supply. A second blood pressure medication his doctor added in early 2025 after his readings spiked runs $156 as well.

Combined, Curtis spends approximately $340 a month on prescriptions alone. His monthly premium is $588. Together, that is $928 a month in health-related costs on an income he expects to land around $54,000 in 2025 — a year where the market slowed back down.

He tried calling his insurer to request a formulary exception. He was told the medications were appropriately tiered. His doctor submitted a prior authorization request for one of the medications; it was denied. Curtis said he spent parts of three separate afternoons on the phone working through that process.

Lifestyle Inflation That Didn’t Help

Curtis is honest about one thing: 2024’s good income didn’t all go into savings. When I asked him directly, he nodded slowly before answering. He replaced his aging car — a 2014 sedan with 138,000 miles — with a 2022 model. He took a trip to Portugal he had been postponing for years. He upgraded his phone plan and started paying for two streaming services he previously shared with a neighbor.

None of those choices were reckless on their own. But together, they meant that when his income dropped back to its historical range in 2025, he was carrying slightly higher fixed costs and a health plan that suddenly required significantly more out of pocket.

“I should have set more aside from that good year,” Curtis said. He didn’t say it with self-pity. It came out flat, like a fact he had already processed and filed away. “But I also didn’t know the insurance was going to go sideways on me the way it did. That part wasn’t in the plan.”

Eleven Months and Counting

When I spoke with Curtis at the tax clinic, he was eleven months away from his 65th birthday — the age at which he becomes eligible for Medicare. His entire financial strategy at this point, he told me, is to hold on.

He has looked at Medicare Savings Programs, which help lower-income beneficiaries with costs, but his income disqualifies him for most assistance tiers. He has not skipped his medications — he has been clear about that — but he has stretched a few fills by a week when cash was tight, something he mentioned almost in passing, the way people mention things they know are not ideal but have normalized anyway.

What struck me, sitting across from him in that library, was how completely he had accepted the math. He was not looking for a workaround or a miracle. He was managing a known problem with a known end date, the way you might drive a car with a slow leak when you already have an appointment at the shop.

What the Tax Return Showed Him

The reason Curtis was at the clinic that morning was to work through his 2025 return. Because his income had dropped back to an estimated $54,000 — he was still waiting on one final 1099 — he might actually qualify for a partial premium tax credit reconciliation in his favor. The volunteer preparer explained that if his 2025 income came in below the level he had projected at enrollment, he could receive a credit on his return.

Curtis listened carefully and took notes on his phone. It was one of the few moments during our conversation when something shifted in his face. Not relief, exactly — more like the specific satisfaction of a calculation finally yielding a number you can use.

His tax situation is also complicated by self-employment. He pays both halves of Social Security and Medicare taxes on his net income, and he deducts his health insurance premiums as a self-employed individual. The volunteer preparer was helping him verify that deduction was being applied correctly — a detail that, if missed, can meaningfully change a self-employed person’s taxable income.

The Resignation That Isn’t Bitterness

Before we parted ways that morning, I asked Curtis what he would tell someone ten years younger who found themselves in a similar situation — self-employed, no employer insurance, income that fluctuates year to year. He thought about it for a moment longer than I expected.

“I’m not the right person to give advice,” he said, and smiled a little. “But I’d say watch your formulary like it’s a bill. Because it is.”

He gathered his folder, shook my hand, and went back to the waiting area. He had another fifteen minutes before his number was called. He sat down and looked at his phone — checking listings, I assumed, the way real estate agents do reflexively, even on a Tuesday morning at a library, even eleven months from a finish line they have had circled for longer than they should have needed to.

What Curtis Kessler’s story reveals is not a dramatic collapse or a single catastrophic mistake. It is something quieter and more common: the cumulative weight of a system that leaves a specific, predictable gap — the year or years before Medicare eligibility — largely to the individual to absorb. For some people, those months pass without incident. For others, they cost $340 a month they do not have to spare. Curtis Kessler is simply among the latter group, and he is waiting.

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