A lawyer can't really tell you what will happen in a novel situation. They can speak with great confidence about legal precedents and where the law is black and white, but once you start walking into the grey areas, where the law isn't clear and there is no precedent, the law isn't a computer program interpreted by machines. There's a whole layer of human judgement in deciding what happens in that case, you don't just overflow onto the stack and get to rewrite the legal code to suit your needs.
So when a lawyer says something like, "Ahh, but the law only talks about 'checking accounts' and 'savings accounts' not 'checking & savings accounts'", at best they are giving you a preview of the argument they will make to a judge or jury at your trial.
Then future lawyers will be able to refer back to the precedents set in your court case with more confidence.
In other words, "this hasn't been tested in court" doesn't excuse them from apparently not bothering to get an opinion from the regulators who have the potential to greatly embarrass them after a high-profile product launch.
"This language doesn't directly violate the rules, and hasn't seen a court case. But it looks like an unsubtle attempt to bypass those rules and a big announcement using this approach is at minimum likely to draw some unfriendly scrutiny."
The law isn't a computer, and regulators - especially in financial spaces - have substantially more freedom than courts to simply reject loopholes. Things like structuring rules are essentially "laws against circumventing the law" for exactly this reason. I'm pretty surprised that Robinhood either didn't get a warning about how poorly this could go, or chose to ignore it.
Regulators have strictly less power than courts here when applying existing law and regulation, though they can write new regulations (but not law).
I guess it's a matter of terminology, but I think there are at least some cases where this isn't true. Ex post facto legislation is permitted in civil law, but it's not something courts can generate in response to a case.
Regulators operating under administrative law can create ex post facto rules wholesale if granted express permission by Congress, which is of course new regulation. But even without that grant, they can create limited retroactive rulings when new interpretations are offered during adjudication. [1] We can debate whether that's 'new regulation' or 'new interpretations of old regulation', but the net result is that regulators are empowered to cover unforeseen circumstances in ways that direct lawsuits are unlikely to offer.
(I am not a lawyer, but...) a move like this looks like an invitation for a Chenery II action, if one is was even needed. The SIPC didn't want to issue brokerage-account protections for a "Checking & Savings Account", and whatever the SEC said to Robinhood produced a very swift change of tune. I suspect it was something like "if we go into adjudication and say magic ampersands don't change your issuing rights, every court in the country will back us up".
[1] http://www.minnesotalawreview.org/wp-content/uploads/2013/02...
I'm not a lawyer, but that line of reasoning sounds like something out of a comedy skit.
"Sure, the law regulates sales of alcohol and sales of firearms, but it doesn't say anything about an Alcohol And Firearms Combo Pack™!"
But there are many types of lawyers in this world. Besides the obvious professional divisions -- real estate vs patent law, trial law vs contract law, etc etc -- you have lawyers who advise their clients versus lawyers who assist their clients. The former are the kind you want, who will tell you what to do to keep everything above board; the latter view it as their job to help you do whatever it is you wanted to do, with the thinnest veneer of "obeying" the "law".
It "works" insomuch as you don't come under scrutiny and your lawyer's legal theories are never tested at trial; a lot of the people making use of this sort of lawyer will rarely if ever actually go to trial -- they'll drag things out until their opponents eventually settle.
[1]: https://www.forbes.com/sites/jeffkauflin/2018/12/13/in-a-bol...
For me it's actually hilarious. The follow-up response letter from the founders group is hilarious. If , robinhood did have a legal team to audit this new tool, they suck ass. They probably made a couple hundo thousand a pop, didnt do any work, and they are now living their lives just a tad richer.