Gingrich inherited the office at the end of November, 1998. The amendment specifically states that it's with MORE than 2 years, which it admiteddly was, but just barely. Almost literally one month more than 2 years. So... does that mean that Gingrich really is inelligible, or could he make a case that it was only technically more than two years?
Technically more than two years is still more than two years. It'd go to the Supreme Court, their hands would be tied, Newt can't run in 2004. You'd hear calls for repealing the amendment, which wouldn't pass Congress, even a Republican dominated one.
Will Newt make any SC nominations? That's always interesting.
Newt, should he win in 2000, should probably try to tie as much of the establishment to his administration as possible. The Bushes in Cabinet positions? Make W SecEd. That'll be funny.

(In all seriousness, that's not an entirely bad idea, particularly if Newt is there to sign off on it).
You might even see Leon Panetta in the Cabinet early, Newt has proved he's willing to work across the aisle.
Romney has talked himself into a hole, saying that Kennedy and Kerry have "abandoned" their state. How can he later run for national office with that rhetoric?
Colin Powell could be SecDef, he'd handle the Afghan war very well.