Is there a trail running shoe with good ankle support?

A: No, I can't recommend a trail runner with good ankle support. Ain't any such creature. The first thing to look for is a runner that emphasizes stability over cushioning. Candidates: the New Balance 805 ($85); Merrell's Rip ($100) and the Salomon X-A Pro ($90). For even more stability, try adding an after-market insole, such as a pair of the Superfeet insoles ($30). These really help your heel sit down in the shoe, for less pronation and less risk of ankle rolling.

Then, invest in a pair of lace-up ankle supports. You want some that are made of ballistic nylon—they should wrap the ankle like a trainer would tape it, then lace up to really lock things in place. Most models cost around $30 and fit under nearly any shoe—the Swede-O Strap Lok is a good example. These things will really give your ankle the support it needs. You lose some flexibility, but that's the trade-off. Even if you found a high-top trail runner or something that worked as such, it wouldn't have even close to the stiffness you'd need to really protect that ankle. The only way to solve the problem—and I have the exact some problem that you do—is to reinforce the ankle independently of the shoe.