It is entirely possible to write plain and understandable english that is legally unambiguous. As someone mentioned above, there has been a huge movement towards this in law schools. It has had some impact, but it's still going to be a long time.
That said, even some of the older folks in the legal field hate legalese. When I clerked for an appeals court judge, we used to do two things: 1. Read every single opinion out loud to all the clerks in order to make sure it sounded sane and was understandable to the other folks at the table, who had no idea what the case was about. 2. Remove all unnecessary words and anachronisms. The judge used to pull out his copy of strunk and white and beat us over the head with it.
Legalese has all manner of special constructs that have to be learned to understand.
(http://www.sourcetext.com/grammarian/less-than-words-can-say...)
> As it happens, that horrid prose serves its aims perfectly. Regulations of this nature have one clear purpose, and that is to answer, before the fact, any imaginable questions that might be asked in a court of law.
There are some problems with The Underground Grammarian, but it's entertaining if you're in the right mood.
As an amateur linguist, I would say that legalese (like Homeric Greek) is a specialized dialect which is both hyperdefined and formulaic (except that lawyers call formulas "terms of art").
As a piece of interesting trivia, Calvert Watkins suggests that formulas of Roman legalese derive from pre-Roman liturgical, magical, and mythological poetics so there probably is a connection between the formulaic dialect of Homer's epics and the legalese of today to the extent that it is related to Roman legalese.
Or the drafter may not be a very good writer! It's easy to fall back on legalese instead of taking the time to make something concise (see the article/video).
Right; there's some cargo culting in legal writing. Until a particular form of words has been tested in court, no-one really knows whether it will stand up.
If there's an untested standard form, most people won't want to experiment with a variation because if their variation happens to be the one that fails, there's a possibility of a negligence suit for not using the standard form.
If there's a tested standard form, even fewer people will want to experiment, for the same reason.
Some? In my experience, it rises to the level of "massive amounts of".