The way it would usually go is that one or more higher-ups whose job it was to optimize pricing decided to get "creative" with the law. People who eventually no

The way it would usually go is that one or more higher-ups whose job it was to optimize pricing decided to get "creative" with the law. People who eventually noticed that things seemed shady/irregular probably spoke up but their concerns were dismissed (with the same reasoning you mention - "the lawyers probably looked at all of this - of course it must be perfectly legal!") and so they stopped wasting their breath. (Probably also on some level Lyft felt like they needed to follow suit in order to compete on price in their most populous and important customer region.) Keep in mind that the lawyers aren't software engineers - if you tell legal that you're doing A but in the code you're actually doing B, they will tell you "A is perfectly legal, keep doing that." They're not going to review the code for themselves.