The emergence of Web 2.0 and some of its ascendant tools such as blogs and wikis have the potential to dramatically change education, both in how we conceptualize and operationalize processes and strategies. We argue in this paper that it is a change that has been over a century in coming. The promise of the Web 2.0 is similar to ideas proposed by Pragmatists such as Charles Peirce and John Dewey. Peirce proposed the logic of abduction as critical for the types of unique/progressive thinking that leads to creative problem solving and/or discovery. While logic based in deduction offers outcomes with certainty, logic based in abduction offers potentially valuable insights. Dewey tried to implement progressive education in the classrooms. Dewey’s ideas, while influential, were often misunderstood, or considered too idealistic and/or unworkable in the traditional classrooms. Logics based in abduction required that different major premises and hypotheses for problem solving be held simultaneously and over time. This type of scenario is often times difficult if not impossible in education based on direct interactions. Hypertext, especially as capture through emerging tools of Web 2.0, may offer the technologies that enable the type of information based networks within the education process that promote abduction and the democratic classroom as Dewey envisioned.