While weev himself is highly unsympathetic, his actual "crime" in this case is quite sympathetic -- it was technically trivial and the results were given to the press, vs. used for financial gain (even though they talked about it). So maybe it's not the worst possible test case.
His biggest mistake was not being in the 9th circuit, though.
(IANAL though, of course)
IAAL :)
But who knows, maybe scotus would get bored enough to find it interesting.
I'm betting "no" in part because legislative fixes are being considered right now. If one passes, it would reduce the odds SCOTUS would ever take the case.
Improper search and seizure leading to a trial is going to have found drugs/guns/whatever, by definition. That doesn't mean the rest of us should have our 4th amendment rights weakened.
For the courts charged with maintaining these protections, it can be hard to keep a hard-line stance in favor of 4th/5th amendment protections in face of a docket that is chock full of actual criminals who actually deserve their sentences.
It's an explanation, not a justification.
2. Generally, if you are smart, you don't bring wildly unsympathetic defendants to SCOTUS at all (IE you don't go to war over them). There are cases it doesn't matter, but one of the reason we ended up with so many 4th amendment exceptions is, IMHO, because of the habit of bringing really unsympathetic people/facts to SCOTUS back when we had justices like O'Connor.