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That's what's so great about the penalty--it's sliding with income, so if you're poor it's cheap, but if you make plenty of money the penalty ends up costing quite a bit more than just buying a policy in the first place. So, okay, he could lie about having policy and not pay the penalty, but it's part of your annual tax bill, which means he's in the crosshairs of the IRS if they ever catch him.
Also, after the initial "let's get everyone going on this new system" rush, open enrollment is now limited to just once a year, so if he gets cancer in January he's fucked until November.
It's not a bad system. There are problems with it that allow the insurance companies to fuck us over, but they were already able to fuck us over in those same ways before. There are now slightly fewer ways for them to fuck us over, but somehow Obamacare keeps getting blamed for all the bases they didn't cover--and not just in a "you weren't thorough" way, but in a "you did this to me!" kind of way.
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