What would you do if you made more money than ever before — and still couldn’t afford to fill your prescriptions? When I first started reporting on the healthcare coverage gap in Wisconsin, I expected to find stories from people at the lowest income rungs. What I found instead, at a neighbor’s block party on a warm Saturday in October 2025, was Estelle Womack — someone who challenged every assumption I had about who this crisis actually touches.
A mutual neighbor had pulled me aside near the end of the evening and said, quietly, “You should talk to Estelle. She’s going through something you’d want to write about.” Estelle, 49, was standing near the food table with a plastic cup of lemonade, laughing at someone’s joke. She looked entirely fine. That, I would later learn, was the whole point.
A Warehouse Supervisor With a Salary — and No Safety Net
When I sat down with Estelle Womack at a coffee shop near her home on the north side of Milwaukee in February 2026, she opened with a line I haven’t stopped thinking about since. “People hear what I make and they think I’m complaining about nothing,” she said. “But on paper is not the same as in life.”
Estelle has worked in logistics and warehouse operations for over two decades. She currently supervises a team of fourteen at a mid-sized distribution facility on the city’s south side, earning approximately $72,000 a year — a salary she worked hard to reach. She is divorced and pays $800 per month in child support for her two teenagers, who live primarily with their father. She also contributes roughly $950 per month toward their childcare and after-school programs, an arrangement she insisted on even though the court order didn’t require it.
What upended everything was a contractor switch at her facility in January 2026. Her employer’s benefits package — which had included health insurance — was restructured as part of the transition. “They gave us sixty days notice,” she told me, pressing her palms flat on the table. “Sixty days, and then you’re on your own.” The group plan she’d been enrolled in ended on February 28, 2026.
Too Much for Medicaid, Too Little for Comfort
Estelle’s first instinct was to apply for BadgerCare Plus, Wisconsin’s Medicaid program. She pulled up the application on her phone the same week she got the benefits termination notice. The answer came back quickly: she did not qualify.
According to the Wisconsin Department of Health Services, BadgerCare Plus eligibility for non-pregnant adults without dependent children in the household is capped at 100% of the Federal Poverty Level — roughly $15,650 annually for a single person in 2026. Estelle earns more than four times that figure. Even accounting for her child support and childcare obligations, those payments do not reduce her countable income for Medicaid purposes in Wisconsin.
With Medicaid off the table, Estelle turned to the federal Health Insurance Marketplace. She logged into HealthCare.gov and ran the numbers. What she found stopped her cold. The enhanced premium tax credits that had been expanded under the American Rescue Plan Act — and extended through 2025 — had not been renewed into 2026 at the same levels. For someone earning $72,000 as a single adult, the subsidy she qualified for was modest. The lowest-cost silver plan available in her Milwaukee county ZIP code came in at $618 per month after her calculated subsidy. Bronze plans started at $480 per month, with deductibles exceeding $7,000.
The Prescription That Made It Real
Estelle has managed hypertension since her early forties. For years, her employer plan covered her blood pressure medication — amlodipine-benazepril — at a $15 copay. The day her coverage lapsed, she went to the pharmacy and paid the cash price for the first time: $338.47 for a 90-day supply. She showed me the receipt on her phone. She’d taken a photo of it.
“I didn’t cry at the pharmacy,” she said. “I paid it and I drove home and then I sat in my car in the driveway and I cried there. Because I didn’t want my neighbor to see me.” She paused. “I don’t want people to think I can’t handle things.”
That composure — what I came to think of as a kind of protective dignity — runs through everything Estelle told me. She is someone who has spent years being the person others lean on: her team at the warehouse, her kids during and after the divorce, her aging mother who lives forty minutes away in Racine. She described her own financial anxiety as something she “folders away” — a phrase that stuck with me — until she has time to deal with it without an audience.
Finding Help — and What It Actually Cost Her
The turning point came in early March 2026, about three weeks after her coverage ended. Estelle’s coworker mentioned that a nonprofit called Covering Wisconsin offered free enrollment assistance through certified navigators. Estelle made an appointment, brought her 2025 tax documents, her termination-of-benefits letter, and her prescription list, and spent two hours with a navigator named Derek.
As Estelle explained it to me, Derek helped her identify a cost-sharing reduction she hadn’t known she might access, and walked her through the difference between the bronze and silver plan structures in practical terms. He also flagged that she might be eligible for the Wisconsin Chronic Disease Program for some pharmaceutical assistance — a referral she hadn’t received anywhere else.
When I spoke with Estelle the week after her new plan took effect, she had just paid her first premium: $487. Lower than the initial quote she’d found on her own, but still more than three times what her employer plan had cost her as a payroll deduction. Her annual deductible is $4,500, meaning any significant medical event this year will land largely on her before insurance picks up. “I have coverage,” she told me carefully, choosing her words. “I don’t know if I have security. Those aren’t the same thing.”
What Estelle’s Story Reveals About the Gap
Estelle’s situation is not unusual — and that’s the part that should trouble anyone paying attention. According to the Kaiser Family Foundation, millions of Americans fall into what researchers describe as the “near-poor uninsured” or coverage gap — people whose incomes exceed Medicaid thresholds but who cannot comfortably afford marketplace premiums, especially without robust employer contributions.
The structural problem is layered. Estelle pays child support and childcare from net, post-tax income. Her housing costs in Milwaukee have risen with the market. She carries a modest car payment and sends money to her mother occasionally when bills pile up. On paper, $72,000 is a solid salary. In practice, after taxes, after child support, after childcare, after housing, she is managing on margins that leave little cushion for a $487 monthly premium and a $4,500 deductible.
When I asked Estelle what she wished more people understood about her situation, she didn’t hesitate. “That ‘doing okay’ is a performance sometimes. I’m doing what I have to do. But I’m not okay the way people think I am when they see me.” She set her coffee cup down. “I’m one car repair away from not being okay at all.”
There was no triumphant resolution to offer Estelle. She has coverage now, and her medication is being managed, and the navigator program connected her with resources she hadn’t known to look for. But she is paying nearly $350 more per month for healthcare than she was before January, her deductible is substantial, and the childcare obligations that eat into her monthly income haven’t changed. She described her current situation as “stable, not solved” — and I think that framing is more honest than most of what gets written about people in her position.
After I left the coffee shop, I sat in my car for a few minutes thinking about the photo on her phone — that pharmacy receipt, $338.47, the number she’d documented like evidence. Evidence of something she hadn’t caused and couldn’t fully fix. She’d shown it to me matter-of-factly, the way you show someone proof that something really happened. I think that’s exactly what it was.
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