Oscar Health: The Bold Bet Nobody Is Talking About
Let me be direct with you. When I look at what’s happening in the US healthcare system right now — the regulatory shift toward individual choice, Trump’s Great Healthcare Plan, and the quiet explosion of ICHRA adoption — one company keeps coming back into focus for me. Oscar Health. And I think most people are sleeping on what this could actually become.
This is the thesis: Oscar is not just an ACA insurer. It is positioning itself as the operating system of the individual health insurance market at exactly the moment the US government is trying to route money directly to individuals rather than big carriers. That alignment is not an accident. It’s a structural advantage, and the window to understand it is right now.
The ICHRA Moment
Individual Coverage Health Reimbursement Arrangements — ICHRAs — were created under Trump’s first term via executive order in 2019 and became available in 2020. The core idea is elegantly simple: instead of an employer picking a group health plan for all of their workers, they give each employee a fixed dollar amount and say “go buy your own insurance.” The employee picks what suits them. The employer gets predictable costs. And the individual insurance market gets a massive new inflow of demand.
For the first few years, adoption was slow. Interesting concept, not much uptake. But something has shifted. From 2024 to 2025, large employer ICHRA adoption grew 34% year-over-year. Small employer adoption was up 18%. Crucially, 83% of employers offering ICHRAs in 2025 had never previously offered health insurance to their workers at all. This is genuinely new market creation, not substitution. Estimates now put total ICHRA enrollment somewhere between 500,000 and one million covered lives, and that number is only going up.
The addressable market here is almost hard to comprehend. Oscar’s CEO Mark Bertolini has done the math publicly: if every employer with fewer than 1,000 employees adopted ICHRA models, Oscar’s targetable market would expand from 21 million lives to 96 million lives. That is the number I want you to sit with. 96 million lives.
Oscar’s Strategic Position
By 2027, Oscar is targeting 18% ACA market share and 150 new metro areas. That’s doubling their footprint.
But the ACA story, while important, is really just the foundation. The more interesting play is ICHRA, and here is why Oscar is structurally better positioned than anyone else to win it.
Oscar is a technology-first insurer. It was built cloud-native from day one in 2012, when every other carrier was running on legacy mainframe infrastructure. Its platform handles member engagement, care navigation, claims, and clinical decision-making in a way that makes the member experience feel like a consumer product rather than a bureaucratic nightmare. When an employer tells their workers to go shop for their own insurance, which carrier has the digital experience, the ease of enrollment, and the plan personalisation to actually win that member? Not UnitedHealth. Not Cigna. Oscar.
They have also been smart about product design. They offer condition-specific plans — diabetes, pulmonary, cardiovascular — that resonate with the kind of members coming off group plans who are used to richer coverage. When employees move from employer-sponsored insurance to ICHRA, they tend to buy silver and gold tier plans, not bare-bones coverage. Oscar’s Chief Insurance Officer has noted this publicly. These are higher-value members, and Oscar has built plans specifically to serve them.
Oscar is essentially building its own digital storefront for the entire individual health market. That is a structural moat hiding in an otherwise overlooked acquisition.
The Regulatory Tailwind
This is where the timing gets really interesting. Trump’s Great Healthcare Plan, unveiled in January 2026, is built around a simple and politically potent idea: stop routing money through big insurance companies and send it directly to individuals. The quotes from the White House are worth understanding. The plan explicitly calls for putting money into healthcare savings accounts so that individuals can go buy their own healthcare. It mandates unprecedented price transparency from insurers. It requires published rate and coverage comparisons in plain English. It forces insurers to disclose claim denial rates.
Every single one of these policies favours a company like Oscar over legacy incumbents. Transparency rewards the insurer with the better digital experience and the cleaner product. Individual empowerment rewards the insurer who has spent a decade building for the individual market, not the group market. And the ICHRA-specific provisions in the Republican reconciliation bill — including a $100 per-month per-member tax credit for small employers who offer ICHRA plans — are a direct subsidy to the demand side of Oscar’s fastest-growing channel.
The White House has been explicit: the administration is committed to building on Trump’s first-term ICHRA progress. Morgan Health’s CEO, backed by JPMorgan Chase, has publicly predicted that the next four years will be a critical growth period for ICHRA products. Private equity and venture capital are pouring into the space. The legislative direction, while messy and subject to Senate negotiations, is clearly pointing toward individual choice and away from centralized group coverage.
The Risks Are Real
I want to be honest with you about the headwinds, because this is FJ Research and we don’t do cheerleading.
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