The open enrollment window for Virginia’s Medicaid expansion program closes more quietly than most people expect — no mailer, no automated call, just a shifted income threshold and a missed month that can cost thousands. That gap was at the center of the story Deshawn Mendez told me when I pulled up a chair beside him in a Richmond Social Security Administration office on a gray Thursday morning in early March 2026.
I was there reporting on processing delays at Virginia SSA field offices, a story that had nothing to do with health insurance. Deshawn was there to request earnings records documentation for a business loan application. We started talking while waiting for our respective numbers to be called, and within ten minutes he had walked me through a two-year financial unraveling that I couldn’t stop thinking about afterward.
A Business Owner With No Safety Net
Deshawn Mendez is 35 years old, runs a seven-employee landscaping operation out of Richmond’s Northside neighborhood, and describes himself as someone who color-codes his budget spreadsheets and still can’t sleep on Sundays. He laughs when he says it, but the laugh doesn’t reach his eyes.
After a decade working as a crew supervisor for a regional landscaping company, Deshawn launched his own business in January 2023 — right as his marriage was ending. His ex-wife had children from a prior relationship, and a court-ordered child support arrangement that her former partner routinely ignored had quietly strained their household finances for years. By the time the divorce was finalized in October 2023, Deshawn was rebuilding from a near-zero savings position while also losing access to employer-sponsored health insurance.
His COBRA premium came in at $1,340 per month. His Richmond apartment rent was $1,100. For the first time in his adult life, his health insurance cost more than his housing.
The Medicaid Question Nobody Warned Him About
Virginia expanded Medicaid coverage under the Affordable Care Act in January 2019, extending eligibility to adults earning up to 138 percent of the federal poverty level — roughly $20,783 annually for a single adult in 2025, according to Virginia’s Department of Medical Assistance Services. On paper, that threshold was nowhere near Deshawn’s income. His landscaping business grossed approximately $310,000 in 2024, and his personal income after business expenses averaged around $68,000.
But the winter of 2024 into 2025 was different. A sustained cold snap in November and December 2024 shut down residential landscaping contracts for nearly eight weeks. Combined with two commercial clients delaying payment past 90 days, Deshawn’s personal income for the first quarter of 2025 dropped to approximately $8,400 — an annualized figure that would have placed him squarely within Virginia’s Medicaid income window.
The confusion Deshawn encountered is not unusual. Medicaid eligibility for self-employed applicants is calculated using modified adjusted gross income (MAGI), which for business owners involves deducting legitimate business expenses from gross revenue. As the Healthcare.gov self-employment guidance notes, this calculation can shift meaningfully from quarter to quarter — but Medicaid enrollment requires documentation of current, projected annual income, not a three-month snapshot. Deshawn’s application, submitted in late January 2025, was denied within 11 days.
The Application Process — and Where It Broke Down
When I asked Deshawn to walk me through the timeline, he pulled out his phone and showed me a folder of screenshots — denial letters, appeal acknowledgments, and call log entries dating back to January 14, 2025. He’s that kind of person: every document saved, every call logged, and still unable to sleep on Sunday nights.
The appeal hearing, Deshawn told me, was the part that still stings. He had prepared a detailed income projection, printed his bank statements, and arrived early. The caseworker cited his 2023 annual tax return — a year when his business had been profitable — as the controlling document.
The Outcome — Mixed, and Expensive
By April 2025, Deshawn’s 18-month COBRA window was approaching its limit anyway. He enrolled in a Silver-tier plan through Virginia’s ACA marketplace during a special enrollment period triggered by the COBRA lapse. His monthly premium, after an advanced premium tax credit, came to $487 — still significant, but $853 less than his COBRA cost.
The plan carried a $4,200 annual deductible, which meant that the three medical visits Deshawn had during the spring — including one for a recurring shoulder injury from years of physical labor — cost him roughly $1,100 out of pocket before insurance contributed anything meaningful.
As Deshawn explained, the resolution isn’t clean. He pays less than he did under COBRA, but more than he’d budgeted, and the deductible means coverage feels theoretical until expenses stack up. His business is performing better heading into spring 2026 — revenue is up about 18 percent year-over-year — but the financial floor still feels uncertain.
He mentioned one regret specifically: he hadn’t known that Virginia’s Medicaid agency allows applicants to submit a prospective income statement using a standardized self-employment worksheet — a tool the Virginia DMAS website describes but that wasn’t referenced in any of the three denial letters he received. He found out about it from another business owner at a Richmond Chamber of Commerce event in June 2025 — four months after his appeal was denied.
What Deshawn Wants Other Business Owners to Know
When our number was finally called at the SSA office — his before mine — Deshawn stood up, straightened his jacket, and offered me a handshake that felt like it came from someone used to dealing with institutions that require you to present yourself a certain way. Before he walked away, he said something I’ve kept thinking about.
The experience Deshawn described reflects a structural tension that exists across most states with Medicaid expansion: the program was designed around employment status and household income thresholds that don’t map cleanly onto seasonal or project-based self-employment. For workers whose income is irregular by nature, the gap between qualifying and actually receiving coverage can be wide enough to cost years of savings.
Deshawn’s landscaping business employs seven people. He carries commercial liability insurance, pays quarterly estimated taxes, and tracks his receivables in two separate spreadsheets. By every conventional measure, he runs a responsible operation. The $16,080 he spent on COBRA in 2024 came directly out of what he’d planned to put toward a business vehicle. That vehicle is still on the lot.
I left the SSA office that morning with a story I hadn’t come looking for. The one I’d arrived to report felt smaller by comparison.
Related: ‘My COBRA Is More Than My Rent’: A Portland Factory Worker’s Race to Medicare at 65
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