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Everybody’s worried about robots taking their jobs. Mark Cuban thinks that’s the wrong worry.
“I hope people realize that for the foreseeable future, the cost of healthcare benefits will get more people fired, or not hired, than AI,” the billionaire posted on X on Sept. 22. (1)
Back in March, he called employer health coverage “usually the 2nd largest expense after payroll,” adding, “Which is insane.” (2)
The numbers back him up. Family coverage through an employer averaged $26,993 in 2025, up 6% in a single year, according to KFF’s annual survey of employers. (3) Workers paid $6,850 of that out of their own paychecks. (3)
Cuban also cited research finding that every 1% rise in health care prices trimmed payroll and headcount at non-health employers by 0.4%. (2)
His fix: a bipartisan bill from Sens. Elizabeth Warren and Josh Hawley that would bar one company from owning both medical providers and insurers or drug middlemen. (1)
I’ve been a CPA since 1981, and I largely agree with him. But there’s a group he didn’t single out that I think is most exposed: workers between 55 and 64.
Here’s why, and how to build a bridge to Medicare if your job disappears first.
1. Why older workers are the easiest cost to cut
Under the Affordable Care Act, insurers in the individual market can charge adults up to three times more based on age. (4) And 64 is where that ceiling bites.
Employers feel a version of the same math. Older workers generally use more care, and that shows up in what a company pays to cover its staff.
That’s the nuance I’d add to Cuban’s point. Health costs don’t hit everyone equally. They land hardest on people who are too young for Medicare and too old to be cheap to insure.
2. If you’re pushed out before 65: COBRA or the marketplace
Lose your job and you can usually keep your employer’s plan through COBRA for up to 18 months. (5) You’ll have 60 days to decide. (5)
The catch is price. You typically pay the whole premium, including the part your employer used to cover, plus 2%. (5) With family coverage near $27,000 a year, that’s a gut punch when your paycheck just stopped.
Your other option is an ACA marketplace plan. Losing job-based coverage generally opens a window to enroll, and depending on your income, you may qualify for a premium tax credit that makes it far cheaper than COBRA.
Run both numbers. COBRA can make sense if you’ve already met your deductible or you’re mid-treatment.
3. The subsidy cliff is back, so manage your income
Here’s where my CPA hat matters most. The enhanced premium tax credits that Congress passed in 2021 expired at the end of 2025. (6) The House voted to extend them in January, but no extension has become law as of this writing. (7)
That means the old “subsidy cliff” returned for 2026. Earn more than 400% of the federal poverty level and you get no premium help at all. (6) In 2026, marketplace enrollees in the 400% to 500% range dropped by 44%. (6)
Older people get hit hardest. KFF estimated a 64-year-old earning $62,700, just over the line, would pay $11,168 more a year for coverage. (8) Among enrollees above 400% of poverty, 51% are ages 50 to 64. (8)
The good news: in early retirement, you often control your income. The marketplace uses modified adjusted gross income, which counts most IRA and 401(k) withdrawals and capital gains, but not qualified Roth distributions. (9)
So in a bridge year, you might live on cash savings and Roth money, keeping taxable withdrawals low enough to stay under the cliff. Sell appreciated stock in a year you’re on Medicare instead of the year you need a subsidy.
One dollar over the limit can cost you thousands. Do this math with a tax pro before December, not after.
Quick gut-check — if your money advice is coming from random online influencers, you’re playing a dangerous game. I’ve been a CPA since 1981 and writing about money since before the internet existed. Sign up for the free Money Talks Newsletter and get expert advice that’s been tested by time.
4. Load up your HSA while you’re still working
If you’re still employed and on a high-deductible health plan, your best defense is money you set aside today for medical bills tomorrow.
For 2026, you can put up to $4,400 into a health savings account with self-only coverage, or $8,750 with family coverage. (10) Once you’re 55, you can add another $1,000. (11) That money stays yours if you lose your job, and it can help pay for care during the gap.
Health Savings Accounts are the only triple tax-advantaged accounts going: contributions cut your taxable income, growth is tax-free, and withdrawals for medical costs are tax-free too. Unlike an FSA, the money never expires.
Lively HSAs charge no monthly account fees, and your balance can be invested for long-term growth. Check out a free HSA today.
One warning: you can’t contribute once you enroll in Medicare. Starting that month, your limit drops to zero. (11)
5. Stay employable, even part time
If health insurance is the expensive part of hiring you, the job that offers it is worth more than its salary. A part-time or bridge job with benefits can carry you to 65 more cheaply than any policy you’d buy on your own.
If you’re hunting for flexible work, FlexJobs offers thousands of hand-screened flexible and remote job listings you won’t find anywhere else, every one scam-free. Explore the listings and see what’s out there.
6. Trim your budget to cover the gap
Even with a subsidy, bridge-year coverage can cost more than you’re used to paying. The fastest way to make room is to find money you’re already wasting.
Forgotten streaming services, free trials that never ended, bills that creep up every year — recurring charges are the easiest money leak to miss.
Services like Rocket Money connect securely to your accounts and put every subscription on one screen — cancel the ones you don’t want in a few taps.
It negotiates cable, internet, and phone bills and flags fee hikes before they hit. Ten minutes could stop the leak for good. See every subscription now.
7. Know your Medicare deadlines and plan the bridge
Medicare starts at 65, and your initial enrollment window lasts seven months: the three before your birthday month, that month and the three after. (12)
Miss it without qualifying for a special enrollment period, and your Part B premium goes up 10% for each full year you could have signed up. (13) That penalty lasts as long as you have Part B. (13)
Juggling COBRA, subsidies, Roth withdrawals and Medicare timing is a lot to get right alone. If you can use some expert help, especially with investing and overall planning, SmartAsset matches you, free, with up to three fiduciary advisors who are legally required to put your interests first. $100K+ in investments? Get matched free in minutes.
The bottom line
Cuban is right that health care costs quietly shape who gets hired and who gets let go. If you’re in your late 50s or early 60s, you’re the most expensive person on that spreadsheet, whether anyone says so or not.
Don’t wait for a layoff notice to start planning. Fill your HSA now. Know what COBRA and a marketplace plan would each cost you. And map out which accounts you’d tap in a bridge year so your income doesn’t blow past the subsidy cliff.
Congress may or may not fix any of this. Your plan shouldn’t depend on it.
The years between your last paycheck and your Medicare card can be the most expensive of your life. They don’t have to be the most surprising.
Sources: 1. Moneywise; 2. AOL (Moneywise); 3. KFF; 4. CMS; 5. U.S. Department of Labor; 6. KFF; 7. CNBC; 8. KFF; 9. HealthCare.gov; 10. IRS; 11. IRS; 12. Medicare.gov; 13. Medicare.gov
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