While he is not regarded as a philosopher in the traditional sense, Oliver Wendell Holmes, Jr. is perhaps the quintessential pragmatist. This is a rare opportunity to read and discuss this seminal figure in American intellectual history. I would encourage everyone to attend.
The basic reading for this meeting is from Louis Menand's anthology Pragmatism: A Reader pages 136-180. This includes the first and third lectures from The Common Law (1881), his essays "The Path of Law" (1897), "Natural Law" (1918), excerpts from two others and his famous dissenting opinion from Abrams v. United States.
For those who wish to do additional reading on the Great Dissenter or who don't have access to the Menand anthology there is a wealth of material available online:
In The Common Law (1881) Holmes sought to bring the ideas and approach of the Harvard Pragmatists to jurisprudence. Transforming the practice of law from a set of rules and principles based on logic, to a tool for adapting in a changing world based on experience. The complete text of The Common Law is available online. The Menand anthology includes Lectures I and III:
In Abrams v. United States he argued that political dissent did not interfere with the war effort and the dissidents should not be punished for their opinions rather than their acts. Holmes was influenced by Zechariah Chafee's 1919 article in the Harvard Law Review "Freedom of Speech in War Time" which is available online:
His essay "The Path of Law" from the Harvard Law Review (1897):
In his majority opinion in Buck v. Bell (1927) he crafts an interesting yet controversial argument concerning the line between public and private welfare. Available online:
There is also an excellent anthology edited by later day Pragmatist Richard Posner called The Essential Holmes available at Amazon: