According to Jon Gruber there should be about one loser from Obamacare for every four winners. From Business Insider:

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It is worth mentioning that this does not  include the impact of the Cadillac tax on employer provide insurance, which beginning in 2018 was designed to make sure certain people got worse insurance from their employer. That is expected to eventually affect millions. This is a provision Gruber championed, so his claim that everyone with employer plans will not be hurt is fairly disingenuous, since it is only true for the first few years.

Gruber also counts all the uninsured as winners even though there are probably at least a small percentage of people in this group that don’t want to buy insurance and will now face a penalty. In their eyes is this a lose.

That said, this seems like a fairly reasonable estimate about the relative number of policy winners verses losers in year one. All laws require some tradeoffs and you can argue this ratio is good enough. Yet it is incredibly disappointing that there was basically zero acknowledgement from the administration that their plan would require it. In fact the administration actively lied to hide this fact, by claiming no one would lose their plan if they liked it. They pretended Obamacare would be all winners and no losers.

If they had admitted their law would require this significant tradeoff, it would have helped show why more progressive reform was so necessary.

If the law included things like a strong public option, direct drug price negotiation, and drug re-importation the law would have been significantly more cost effective. These provisions would have saved hundreds of billions while reducing premiums across the board. With just those few provisions the law could have been written so there was more like 20-40 winners for every one person made slightly worse off by the law. It would have been mostly just highly profitable drug companies losing out instead of middle class families.