I think that one of the ultimate strengths of Pragmatism lies in its very essence. The aspect of "practice" as being a part of "theory" is appealing. To be honest, in a domain where so much of thought is rooted in meaningless activities that are divorced from daily consciousness and being in the world, Pragmatism is different from all other schools of thought. The demand for "value" in what one does and thinks becomes really essential to the Pragmatist. Along these lines, the need to look at different disciplines as being "different tools for different jobs" is something that is refreshing. Pragmatism was ahead of the curve in understanding how the globalized view of the world, armed with the internet was going to come around the bend. Rorty and other Pragmatic thinkers were "globalized" before the term became part of the landscape.
If there might be a weakness to the school of thought, it would be in its lack of assertion of a set of prescribed and totalizing values. For a school of philosophy, Pragmatism really breaks the rules in that it does not have a strong philosophical dogma attached to it. Thinkers like Rorty found philosophical value in literary works from Orwell, Flaubert, and Nabokov in the ability to expand more imagination. This is something that most philosophical thinkers would not presuppose. In this, Pragmatism offers a challenge to the individual who feels the need to embrace a standardized and solely limited view of the philosophical line of enquiry.