After four rounds of Freelancer Madness — and lots of close calls and upsets — the biggest villain of freelancing has been crowned. And perhaps it will come as no surprise that the biggest villain of freelancing, as voted by freelancers, is the American Healthcare System.

The American healthcare system beat out a worthy adversary — the Cost of Living — but we all know what a pain point healthcare is and has been for freelancers. With healthcare tied to employment, freelancers are left in the lurch, with few comprehensive healthcare options available.

When the “One Big, Beautiful Bill” Act became law in July 2025, we knew this would only exacerbate an already precarious situation. The bill failed to extend the premium subsidies that lessen the cost of state marketplace health plans, added additional hoops for anyone seeking to purchase a plan through the marketplace, and gutted Medicaid.

Freelancers power our economy. They’re tired of being left behind, and rightfully so. Per a healthcare survey we circulated in late 2025, 91% of freelancers said they want to see the ACA subsidies extended. 82% of freelancers said that access to healthcare is an issue that affects how they vote — a key touchpoint to consider ahead of the June 2026 midterm elections.

While all sixteen of the entries into our Freelancer Madness bracket were worthy adversaries, each annoying pain points in their own right of daily freelancers, Freelancers Union is working towards a future where we hope to eliminate all of them.