Yale Law Professor Jack Balkin blogs on the future of Don't Ask Don't Tell. If 2008 ends with a Democratic Congress and a Democratic President, as seems very probable, then he thinks it's gone. Barring that, things get a bit more fluid. But one interesting side-story is the potential for a court challenge.
Don't Ask Don't Tell has been upheld thus far in every lower court which has heard it. But these decisions all came in the early-mid 90s, when views on gays hadn't progressed as far as they have today. This wouldn't matter, except that there apparently a case pending now before the 1st Circuit (based out of Boston), a reasonably liberal appellate court which could shake the boat. By itself, this wouldn't do much, but the circuit split would greatly enhance the likelihood of Supreme Court review. In that case, all eyes would be on Justice Kennedy (huge surprise, I know), who has written two straight opinions strongly in favor gay rights (Romer v. Evans and the path-breaking Lawrence v. Texas). Nonetheless, the court is generally far more deferential in cases involving the military, so it really is a toss-up.
Though the conciliatory side of me wants this decision to be decided by democratic branches, a big part of my heart wants the courts to be the ones to strike down DADT. It really is a gross insult to gay and lesbian Americans, and wildly inconsistent with equality under the law. I want a paper record of America's Justices explaining that very fact, so in future generations people will have something to point to akin to Brown. Lawrence did that to some extent -- but, social controversy aside, court decisions seem to have different moral weight on our descendants than mere legislation.