Why “Is This Legal?” Is The Hardest Question I Get As A Lawyer

In the three years I've been in private practice, every client who has ever called me has asked some variation of "is such and such legal?" I never really know how to respond in the moment because the answer is usually more complicated than the client is prepared for. From the outside, it's easy to assume that the answer is a simple yes or no, as if there was a bright line that divided legal and illegal behavior. I too labored under the same belief when I went off to law school; I just assumed that law school would teach me where that line was and what sat on either side of it. But I was rudely disabused of that notion in my first semester torts class when the professor’s canned response to any hypothetical from the class was “it depends.”

The truth is, the law is rarely cut and dried. All laws have exemptions and immunities. Sometimes new laws come into being and replace old laws and no one really knows how they will apply. Sometimes old laws fall out of practice but never come off the books, waiting for creative attorneys to bring them back into the fold. Some laws that seem well-settled can become unsettled if the political landscape changes or unforeseen situations arise that allow for new interpretations of the law. And even where the law is settled and in no danger of becoming unsettled, no two cases are ever exactly alike, so the principles that apply in one case make not apply in another, even if they look similar to a casual observer.

What I’m saying is that the reality of practicing of law cuts against simple answers like “yes that is illegal.” A question like that requires me to do several hours of investigation to determine whether a law applies to a particular client’s case, and if so, how. So when a client pays me, they’re paying for my research and analysis abilities as much as my counsel.

Because my law practice is transactional, the question is usually posed to me in the context of a contract negotiation. A client will approach me with a contract from a potential employer and ask me if such and such provision is legal. In those cases, the question is less about the legality of something and more about its enforceability. In other words, a contract provision may not be enforceable under generally accepted contracting principles, but most of the time it’s still legal to put it in there (unless the provision motivates criminal activity). You just wouldn’t be able to have a court legally enforce it.

We use terms like “legal” and “illegal” as a useful shorthand to describe whether an action we want to take – or someone wants to take against us – is going to have negative repercussions. It’s certainly easier to say something is illegal than to list all the statutes and their exemptions, or to list all the variations in common law over the past two hundred years. But those words are misnomers because they don’t accurately convey how our jurisprudence really works.

I often tell my non-lawyer friends to think about the law less as firm and unyielding strictures and more like flexible guidelines. They can generally tell you what kinds of activity can get you arrested or sued. They can generally tell you when exceptions apply. But since each case is determined on its own merits, the ultimate question of whether something is legal or illegal will depend largely on the facts of the case and the ruling of a judge or jury. A talented lawyer can argue against the illegality of an action (and we’ve seen this play out dozens of times, notably in the O.J. Simpson and George Zimmerman murder trials). And because judges and juries are regular and imperfect people, with all kinds of attendant biases and beliefs, those arguments may carry weight or not.

At the end of the day, I can tell a client whether something is LIKELY to be illegal based on the law (if you read this blog, you’ve probably noticed by now that whenever I quote the law, I qualify it with “usually,” “generally,” or “typically”), but I would also tell them that I can’t make that determination for them. And anyway, my clients aren’t really concerned with the words. They just want to know if there’s a danger of getting arrested or sued. And I’m happy to provide that counsel to them... after I explain that the answer they’re about to get will be a lot more complicated than the one they were expecting.