Even in Machiavelli's own time, his ideas were regarded as immoral by many, and the ruthless, cunning, cynical, exploitative "Machiavel" became a stereotypical figure on the Elizabethan stage. Whether such figures truly represented the full moral subtlety and actual intent of Machiavelli's philosophy is a question too complicated to discuss here. Suffice it to say that "Machiavellianism" has become synonymous with political amorality or immorality.
In recent American politics, some have seen Richard Nixon as a Machiavellian figure (however justly or unjustly). Dick Cheney has been perceived by some as another such figure (again, I say nothing about the justice of such claims). Notice that in each of these two cases, the assumption is that the Machiavellian figure is actually highly intelligent, or at least not stupid. Almost by definition, Machiavellian figures are shrewd and intelligent, as are (for example) Shakespeare's Iago and his Richard III.
Certainly there appear to be many parallels between pragmatism in Machiavelli's day and pragmatism today, especially regarding the way in which rulers are advised in Machiavelli's works to variously manipulate and abuse their followers to secure power and their goals. Unfortunately, there appears to be many ways in which this is the case nowadays, with rulers being true students of Machiavelli in the way that they use and maintain their power.
According to a moralist view, Machiavelli's pragmatism equated (in simplistic terms) to success in political endeavors. This success was sought without adherence to norms of morality, if need be, for Machiavelli viewed moral behavior as an unnecessary impediment, as he makes clear in Chapters 15 and 18: "learn how not to be good." This compares very closely to pragmatism in contemporary politics, which involves "dirty" politics and "dirty tricks" to get the goal attained at virtually any cost.
If we define "pragmatism" as a sense of the real world injected in politics, then I think there is much in way of connection between Machiavelli's work and the modern condition. When we use "pragmatism," though, I think we are referring to a practical way of viewing the political world. It is not one as much as the pragmatist philosophical viewpoint, but rather a world political view, realpolitik, that embraces power as the ultimate end. In this light, Machiavelli's work is a pragmatic one. He does not attribute failures and shortcomings to such ethereal realms as fate or lack of divine providence. This realpolitik approach concerns how individuals need to be ruled, how to approach the subjects with issues of unpopularity, and the most important elements in order to continuing ruling effectively. These elements are evident today in the modern setting. While the rule of sovereigns has been replaced for the most part by liberal democracy, the ideas of how to interact with subjects, how power becomes the defining element to one's rule, and how subjects need to be controlled is still there in the modern setting. The inventions of press conferences, "spin doctors," tracking polls, and the construction of competing sides to forge a beneficial end for the Status Quo are still elements that are found in Machiavelli's work. Machiavelli believes that his work is an actual handbook that outlines how a ruler can approach the task of political rule in a manner that controls the body politic in accordance to the will of the sovereign. For Machiavelli's work, the fundamental precept in the political setting is that of power. This is a practical approach to govenance, one that he believes is something that can be taught. It is also something found in the modern setting.