I tore the ligaments in my L ankle way back in 9th grade and to this day I still roll my ankle, but I have learned to deal with it in different ways. For starters I make sure that if I have a bad pain that I do RICE treatment, but I also work to strengthen my ankles. I do some of these exercises that I found on active.com http://www.active.com/fitness/Articles/12_Ways_to_Build_Ankle_Strength_for_Top_Performance

Right now with running I just make sure that I'm watching the ground to make sure that I don't step on a root or rock. With running you just have to accept that you might strain your ankle but don't let it stop you. If you're really afraid try to find a elastic brace to wear, but know that it can cause blisters. The one time I wore a brace I had foot pain in my arch and I knew that it wasn't worth wearing a brace if I couldn't even walk right.

Go to a running store and ask them to help you find the right shoes for you. I know that my ankles roll out when I strike with my heel but then roll in when I move through the foot contact. They can help find the right shoes that will stabilize or cushion or give you the right amount of both!

Good luck!