Several comments:
(1) if you made a bet with someone, and loser was to put a phrase in his sig, and he lost, and he (apparently) put the phrase in his sig but then just isn’t displaying his sig, then that is weaselly of him… but, ironically, that’s precisely the kind of legal parsing that you’re applauding in this thread. If you made a poorly worded bet with him which allowed him to change his sig and not display it, why, of course he would take advantage of that poor wording and exploit the loophole. It’s almost like there’s a parallel there of some sort to this current thread!
(2) There was an earlier exchange in which someone (I’ve lost track of who) claimed that this was an unethical or inappropriate topic for betting, and you asked why, and I don’t think anyone answered. And, at least from my perspective, it’s unethical for the same reason that it would be unethical to place bets about whether someone about to get the electric chair will soil himself or not, or an over-under on the number of Palestinians who will be killed by Israeli rockets next week. Given that this law potentially saves actual human lives (by providing medical care to those who don’t currently have it), betting on it has a strong tinge of bloodsport, of betting on human lives, of gladiatorial combat, of rich guys paying bums to fight each other to the death, etc. That’s why it seems tacky to me, particularly if you are offering to bet someone who is potentially directly affected by the lawsuit. (However, unlike many people in this thread, I have absolutely zero problem with you generally expressing your confidence via offering monetary bets, and I understand your motivation for doing so.)
(3) More generally, I think there’s an interesting question about what to do when a law is “written poorly”. I think we all agree that there are possible “typos” that are so minor that they should be immediately overlooked… you can get some pretty weird laws by misplacing a comma or reversing “no” to “on”, or putting the decimal point in what is clearly and comically the wrong place. At the same time, legislators certainly shouldn’t be allowed to say “oh, hey, remember that law we passed last week which established a 6% tax? Well, that was a typo, we mean’t 16%, that’s what we really thought we meant, pinky swear”.
I think this case is somewhere in between those two examples. Given my general lack of precise legal knowledge, I wouldn’t find it prima facie outrageous either for the courts to decide “the context, and the historical record, makes it clear that this section refers to all exchanges”, or “well, the law says what the law says, we have to follow the text”. However, something that I think ought to carry a LOT of weight is whether the record of the debate on the law indicates that everyone, both for and against, agreed with what the law meant. If there’s a law banning the import of apples (the fruit), and people debate it a lot, and all the debate is about the benefit of that particular fruit, and the law is passed, and later someone noticed that the person who was getting the scientific names for the apples messed up and in stead of banning the 5 known varietals of apples, it bans 4 of those 5 plus one varietal of figs… that’s a situation where I think the court should rule that the law is clearly intended to be banning apples, not 4/5s of apples and 1/7th of figs.
In any case, I do find the behavior of many Republicans, in context, to be pretty abhorrent, given my absolute certainty that what motivates the vast majority of them is not actual philosophical objection to Obamacare (given that it was a Republican idea to begin with), or a passionate believe in the importance of really precisely worded laws (because most of them, although possibly not you, would be humming precisely the opposite tune if the law with a flaw in its wording was one they supported), but simply a desire to make Obama fail, with very little caring that their actions actually hurt real people. However, fortunately or not, THAT certainty of mine is one that it’s hard to bet about.