You may want to look fairly closely at employment prospects. I think you are probably a bit over-optimistic that landing a solid well paying job is easy if you do alright. If you do extraordinarily well your shots aren't terrible, but anything less than that and I wouldn't count on being able to make much in the first few years. The legal market is just really lousy right now and there are enough unemployed or underemployed lawyers in the pipeline I don't see things turning around any time soon. Legal academia can be a great life, but from all accounts most legal faculties are exceptionally picky about credentials and brand-name schools. If you are serious about legal academia it may be worth doing whatever it takes to land HYS. If your academic interests are other than legal, then focus primarily on that other field and pickup a jd if you've nothing better to do. A PhD will help quite a lot with legal academia provided that it is related and you write something decent (particularly if you get your jd somewhere other than hys). I'm also interested in legal academia and have been looking at this quite a bit - I don't argue that the current system is as it should be, just stating my observations of how things are.