He Paid Into Social Security for 20 Years — Then His Disability Check Came Up $800 Short Every Month

The man ahead of me in line at a Walgreens on Summer Avenue in Memphis was speaking quietly to the pharmacist, his voice low enough…

He Paid Into Social Security for 20 Years — Then His Disability Check Came Up $800 Short Every Month
He Paid Into Social Security for 20 Years — Then His Disability Check Came Up $800 Short Every Month

The man ahead of me in line at a Walgreens on Summer Avenue in Memphis was speaking quietly to the pharmacist, his voice low enough that I almost missed it. He was asking whether there was a program — any program — that could help him afford a bottle of prescription muscle relaxants he was holding in his hand. The price tag on the bag read $187. He set it back on the counter and asked her to hold it while he figured something out.

I introduced myself outside. Curtis Trujillo, 42, had the kind of hands that tell a whole career — calloused, scarred at the knuckles, with a fading cut across his right palm. He was a licensed plumber. Or he had been, until January 2024, when a pipe trench collapse on a commercial job site left him with two herniated discs and a future he hadn’t planned for.

He agreed to talk. We sat in his truck in the parking lot for nearly two hours.

The Injury That Rewrote Everything

Curtis had been in the trades since he was 22. He told me he cleared roughly $52,000 in 2022 and about $49,000 in 2023 — solid income for Memphis, he said, enough to keep himself afloat, split rent with a roommate in a house near Bartlett, and put a little away each month. He never had children, never married, and described his financial life as “simple — just me.”

The collapse happened on a Tuesday morning in January 2024. A retaining wall gave way on a commercial excavation site. Curtis was in the trench. He was pulled out, taken by ambulance, and told by the ER physician that he had sustained significant lumbar damage. Surgery was discussed. Physical therapy was ordered. Returning to plumbing — the crouching, the lifting, the torque on pipe wrenches — was ruled out indefinitely.

“I didn’t even know what SSDI was. I just knew I’d been paying into Social Security my whole working life and I figured that meant something. I never thought I’d need it at 41.”
— Curtis Trujillo, licensed plumber, Memphis, TN

He filed for Social Security Disability Insurance in February 2024, about five weeks after the injury. His employer’s workers’ comp coverage was disputed — a detail still caught up in a legal process as of the date we spoke — and he was left waiting with essentially no income.

Eight Months of Waiting — And What That Cost Him

According to the Social Security Administration, the average processing time for an initial SSDI determination is three to six months, though many applicants wait significantly longer. Curtis waited eight. His approval letter arrived in October 2024.

$1,342
Curtis’s monthly SSDI benefit

$2,110
His estimated monthly expenses

$768
Monthly shortfall

The back pay he received covered five months — roughly $6,710 before any withholdings. It sounds like a windfall until you realize he had already borrowed against it. Over those eight months of waiting, Curtis had leaned on two credit cards to cover rent, groceries, utilities, and prescriptions. By the time his approval came through, he had accumulated approximately $8,400 in credit card debt at interest rates between 24% and 27%.

His credit score, which he said had been around 680 before the injury, had dropped to 542 by the time he cleared the debt partially with his back pay. The rest — about $3,900 — remained on a card. “I used the back pay to pay off what I could and keep the lights on,” he told me. “What was left wasn’t enough to wipe the slate.”

⚠ IMPORTANT
SSDI recipients must wait 24 months from their date of entitlement before Medicare coverage begins. For Curtis, whose entitlement date was set to May 2024, Medicare eligibility would not begin until May 2026 — meaning he spent nearly two years without health insurance coverage through the program. During that window, prescription and medical costs fall entirely on the individual unless they qualify for Medicaid.

The Medicare Gap Nobody Warned Him About

When I asked Curtis whether anyone at the SSA had explained the 24-month Medicare waiting period, he shook his head slowly. “They sent me a letter saying I’d get Medicare eventually. I didn’t read the fine print close enough. I thought it was going to kick in pretty soon after I got approved.”

As explained by Medicare.gov, most people who qualify for SSDI automatically become eligible for Medicare after a 24-month waiting period that begins with their month of entitlement — not their approval date. That distinction matters, because the entitlement date can be set up to 12 months before an approval letter arrives, depending on when the SSA establishes disability onset.

For Curtis, that meant his Medicare start date was calculated as May 2026 — roughly two and a half years after his injury. From October 2024 onward, he was receiving SSDI checks but paying fully out-of-pocket for prescriptions: a muscle relaxant, a nerve pain medication, and a twice-daily anti-inflammatory. Together, those three prescriptions ran him between $310 and $380 per month depending on the pharmacy and whether coupons from GoodRx applied.

“The medications are the only thing keeping me functional. I can’t just stop taking them. But every month I have to decide what else doesn’t get paid so I can afford them.”
— Curtis Trujillo

He had applied for Tennessee’s Medicaid program, TennCare, in late 2024. He was denied — his SSDI income, while modest, placed him above the eligibility threshold for his household size under the state’s current expansion parameters. He was, as he put it, “too broke to pay for insurance and too rich to get the free kind.”

What He Found — and What He Didn’t

By the time I met Curtis at that Walgreens in March 2026, he was two months away from his Medicare start date. He had found partial relief through a combination of sources he’d pieced together largely on his own.

How Curtis Closed Part of the Gap
1
NeedyMeds.org — Connected him to patient assistance programs from two pharmaceutical manufacturers, reducing one medication to $0/month.

2
GoodRx coupons — Reduced his anti-inflammatory from $94/month to $31/month at a specific pharmacy chain.

3
Local community health center — A federally qualified health center (FQHC) in Memphis offered sliding-scale physician visits, reducing his follow-up appointment costs significantly.

4
Medicare savings program research — A social worker at the health center helped him identify that he may qualify for the Medicare Savings Program once Medicare begins, which could eliminate his Part B premium of $185/month.

Even with those resources, his monthly shortfall remained around $400. He was still dipping into what little he had left from his back pay — which, as of March 2026, was down to approximately $900. “I’m basically watching a clock,” he told me. “When that runs out, I don’t know exactly what happens.”

KEY TAKEAWAY
SSDI recipients under age 65 must wait 24 months from their entitlement date before Medicare coverage begins. During that window, prescription and medical costs are not covered by either SSDI or Medicare — a gap that falls hardest on people with significant ongoing medical needs. According to KFF research, approximately 1.7 million people with disabilities are in this waiting period at any given time.

The Part He Won’t Tell His Friends

I asked Curtis whether the people in his life knew what he was going through. He laughed, quietly and without humor.

“My friends think I’m just taking it easy while my back heals. I haven’t told any of them I’m on disability. There’s a shame to it that doesn’t make a lot of sense logically, but it’s there. Like I failed at being a grown adult.”
— Curtis Trujillo

He had told his roommate only that he was “having some money issues” — nothing more specific. The isolation of navigating a benefit system while managing chronic pain, damaged credit, and the psychological weight of an identity built around skilled labor — it was all compressed into that quiet request at the pharmacy counter I had happened to overhear.

What stayed with me as I drove away from that Walgreens parking lot wasn’t the dollar amounts, though they were stark. It was the specific, grinding quality of a situation where the system technically worked — he applied, he qualified, the check arrived — and yet the outcome remained precarious. Curtis did everything right. He paid into the system for 20 years. He filed promptly. He found workarounds that most people never discover.

And still, as of April 2026, he was spending down the last of his reserves, two months away from a Medicare card that might finally stabilize things — or might introduce a new set of costs and decisions he hadn’t fully mapped yet.

“I just want to get to May,” he told me before I got out of the truck. “After that, maybe I can breathe for a minute and figure out what’s next.”

I hope he gets that minute.

Related: She Was Already Paying More for COBRA Than Rent. Then a Scammer Posing as Social Security Called.

Related: She Built a Retirement Spreadsheet Down to the Penny — Then a Treasury Offset Took $320 From Her First Social Security Check

Frequently Asked Questions

How long do you have to wait for Medicare after being approved for SSDI?

Most SSDI recipients must wait 24 months from their date of entitlement — not their approval date — before Medicare coverage begins. The SSA sets an entitlement date that can precede the approval letter, sometimes by up to 12 months. According to Medicare.gov, this 24-month waiting period applies to most people under 65 who qualify through disability.
What is the average monthly SSDI benefit payment?

According to the Social Security Administration, the average monthly SSDI benefit for a disabled worker was approximately $1,537 as of early 2025. Individual amounts vary based on a person’s lifetime earnings record — Curtis Trujillo’s benefit of $1,342/month reflects his specific earnings history before his injury.
Can you get Medicaid while waiting for Medicare on SSDI?

It depends on your state and income. SSDI income can place recipients above the Medicaid eligibility threshold in states with more restrictive rules. Tennessee, where Curtis lives, has not fully expanded Medicaid, which contributed to his denial of TennCare coverage despite his limited monthly income of $1,342.
What prescription assistance programs are available for SSDI recipients without Medicare?

Options include pharmaceutical manufacturer patient assistance programs searchable through NeedyMeds.org, discount programs like GoodRx, and federally qualified health centers (FQHCs) offering sliding-scale services. Curtis reduced one medication to $0/month and another from $94 to $31/month using these resources.
Does being on SSDI hurt your credit score?

SSDI status itself does not directly affect your credit score. However, the income reduction that accompanies disability often leads to missed payments and increased credit utilization. Curtis Trujillo’s score dropped from approximately 680 to 542 during his 8-month SSDI wait due to credit card dependency and payment difficulties.

199 articles

Sloane Avery Wren

Senior Benefits Writer covering Social Security, Medicare, and retirement policy. M.P.P. University of Michigan. Former CBPP researcher. NSSA Certified.

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