Unless a matter is blatantly criminal the advice from the army of lawyers is usually just one of many factors taken into account when assessing the risk/reward. It's rare for management to ignore the advice of counsel completely but it's definitely not unusual for executives to have a higher risk tolerance than the attorneys.

Those armies of high paid lawyers are not always right. Plenty of companies get it wrong and then pay the price in court.

If the "downside" is paying fees in court, then it's a simple calculus for when it's worth it to follow the law and when not to. You're just doing business exchanges now with the legal system.

i guess the point isn't that they are right or wrong, it's what it takes to even decide that. high paid lawyers will need more high paid lawyers against them with zero guarantee of success.