If you asked most traders about Oscar Health, they’d probably squint and say, “Oh yeah… wasn’t that supposed to be the Robinhood of healthcare?” It was. Until it wasn’t. The company went public in 2021, and instead of minting gains like every other garbage SPAC that year, Oscar somehow managed to fumble the IPO bag immediately… dropping 11% on day one (which, let’s admit, is very hard to do). And then it got worse… Shares tanked over 80% within months. Since then? Radio silence. Which is what makes the past week so weird…

Shares of the so-called “tech-powered” health insurance company are up nearly 52% in a little over a week, and no one really knows why. There was no earnings surprise. No front page M&A headline. Not even a lazy press release full of buzzwords about how they’re using AI to revolutionize patient care.” Just pure mystery and a whole lot of Reddit.

So the obvious question is: Is this another Trump bump in the making? Or is WallStreetBets just thirsty for chaos again? Let’s start with the conspiracy board material (this is what you really care about). Oscar’s vice chairman is Joshua Kushner… little brother to Jared Kushner, aka Ivanka’s husband, aka Trump’s right-hand man during his first White House run. That makes Oscar Trump-adjacent, and in this market, that’s apparently enough to add on a couple extra billion in market cap. 

To be fair, the “Trump effect” has receipts. Remember Dominari Holdings? That thing exploded out of nowhere on rumors of Trump ties. Or Unusual Machines, which went vertical the moment someone shouted “Trump drone deal” into the Twitter void. So yeah, retail traders are betting Oscar might be next in line for the presidential seal of approval. 

But let’s not act like this isn’t also looking a lot like your typical Reddit-fueled fever dream. Oscar has suddenly become one of the most mentioned stocks on r/WallStreetBets. Call option volume cracked over 150,000 contracts traded on Wednesday alone, compared to the 20-day average of just 33K. Nearly 50 million shares traded hands that same day. That’s the kind of volume you expect when a company announces a buyout… not when a health insurer just starts randomly spiking for no real reason.

So, the fundamentals aren’t garbage. Oscar posted 48% revenue growth in 2023 and followed that up with 57% in 2024. It turned in a respectable $0.92 EPS in Q1 2025, and even claims to be a “tech” company, which is kind of like every Burger King suddenly calling itself a “food innovation platform.” It’s technically true, but let’s not get carried away.

And then there’s the Medicare part. This week, lawmakers floated a proposal for a new “Part E” Medicare option… a self-funded version that would live alongside private insurers. While it might increase competition, it could also buy some time for Medicare’s financial doom clock and open new lanes for private companies like Oscar to swoop in. Some people think there’s an opportunity here. Others just see more policy spaghetti getting thrown at the wall. Either way, the market noticed.

Can this run keep going? Sure. And I could also wake up tomorrow with Elon’s bank account and a full head of hair. If you're buying into this Oscar Health hype, you’re either related to Trump or an insider at the company.

At the time of publishing this article, Stocks.News holds positions in Robinhood as mentioned in the article.