For a success/failure discussion, we should break the WOT down into the specific campaigns and initiatives.
Iraq
Afghanistan
Gitmo
Patriot Act
Domestic Spying
Rendition Programs
others??
Each of these need to be evaluated individually for any kind of valid conclusions.
domestic security might be another area. How well are our ports being protected? How well are the borders being enforced? How successful have programs to protect drinking water or other major potential terrorist targets been.
OK, and my wild guess at an assessment:
Iraq
disaster - corruption, and ineptitude have contributed to overall mess which has weakened US enormously and encouraged US enemies and in the end is likely to provide terrorist recruiting areas. Overall large negative in WOT.
Afghanistan
bad situation - probably though modest positive in WOT given the disruption of al-qaida and the capture of various operatives. Offset significantly by bad situation in Afghanistan that might generate terrorist actions against US or its partners.
Gitmo
What to do with prisoners from Afghanistan looked to be tough for anybody to deal with. Human rights abuses have lost friends. Personally, I am opposed to mistreatment of prisoners to the degree that it seems to have been practiced here. None the less probably in net Gitmo positive in WOT.
Patriot Act
Not sure. Just don't know enough to even hazard a WAG.
Domestic Spying
Doubt much has been gained here. The rumors about the big scanning programs looking for people saying bomb or something is that they generate way too many leads to be useful. Still I'm inclined to believe some positive benefit to the WOT from this. Albeit coming with the risky expansion of federal powers, especially in the hands of this administration.
Rendition Programs
Obviously, a very disgusting business. Clearly innocent people have been caught up in this for which no apologies have been offered. I just don't know what the balance is here but I'm going to hazard a guess that program has had very little benefit. And that benefit may be mitigated or eliminated by loss of US prestige and increased reluctance of foreign countries to cooperate with US as a result of these programs.
domestic security
A lot has been done. Who knows how much has been helpful. Probably an enormous amount of wasteful spending has been tacked on and to some degree when the country is weakened by profligate spending the WOT suffers. Politics has worked to prevent some port security improvements and this is an area where the US seems to be vulnerable. If you throw improved airport security into this subsection, then overall domestic security has been improved substantially, but how much of that improvement came from the simple expedient of securing aircraft flight deck doors? Probably in terms of bang for the buck no single security expenditure was remotely as beneficial as that. So my guess on this subsection is that there has been a substantial improvement in the WOT, although apparent corruption and incompetence in homeland security plus very slow progress in developing communication systems to allow all aid agencies to communicate in an emergency and almost complete failure to control borders for years after 9/11 are problems.