He earned B.A. in Modern History from Cornell University, where he studied political philosophy with Allan Bloom, and an M.A. and Ph.D. in Political Philosophy from Harvard University under Harvey Mansfield. He is a Professor of Political Philosophy at the University of Toronto, where he has taught for more than twenty five years and where he currently serves as Chair of the Munk Centre's program in Political Philosophy and International Affairs.
He is often identified as a Straussian and is critical of theories that identify Leo Strauss with neoconservatism and the War in Iraq. He supports the Democratic Party, but is critical of its left wing.
He has held a Guggenheim Fellowship and an NEH Fellowship. He has been a Fellow at the Sheldon Chumir Foundation for Ethics in Leadership, and in 2003 he received the school's Outstanding Teaching Award.
Multilingual, he can speak English and French and read Hebrew, Latin and Ancient Greek.
He has written and translated articles on Herodotus, Thucydides, Plato, Machiavelli, Montesquieu, Churchill, Charles Taylor, American religion, and humanitarian military intervention. His books are The Humanity of Thucydides (1994), and The Legacy of Rousseau (1997) edited with Nathan Tarcov.
He projects a book on the role of compassion in modern political thought and practice, and a study of the Book of Esther. He describes Rousseau as "the modern philosopher with whom I'm most familiar".
He is a director of Energy Probe Research Foundation, an anti-nuclear environmental organization based in Toronto. 
The Chair of the University of Toronto Political Science department has said of him: "If there is another observation to be made or argument to be explored or interpretation to be developed, Cliff wants to hear it."
He has written of his teaching method: "My methods harken back to an older kind of warfare: 'Don't teach until you see the whites of their eyes.' Eye-to-eye teaching resembles hand-to-hand combat. Teacher and student struggle, and if they're lucky both lose -- each is compelled to learn from the other. It's not a relation of equals, and teachers who pretend that it is should find another calling, like talk show host. But neither is the role of the student passive."
A number of Orwin's students have become teachers and scholars themselves in a range of disciplines. These include: Norman Doidge, a psychiatrist with affiliations at the University of Toronto and Columbia Medical School; Janis Freedman Bellow (the widow of Nobel Laureate author Saul Bellow) who lectures in English at Tufts University; Robert Howse, a professor of international law and legal and political theorist at NYU Law School who also has a research affiliation with the University of Paris I (Pantheon-Sorbonne); Christina Tarnopolsky, a political science professor at McGill University who formerly taught in the Government Department at Harvard; and Nathan Busch, a political science professor at Christopher Newport University, and helped develop the Center for American Studies at Christopher Newport.
- See this essay from May 2006 on Leo Strauss; Orwin is concerned to argue against identification of Strauss as a neoconservative, and other positions.
- Desch MC., "What Would Strauss Do?" The American Conservative, January 17, 2005. Accessed June 3, 2007.
- Gottfried P.,"In Response to a Courteous Critic," LewRockwell.com, June 17, 2006. Classes Orwin with: Allan Bloom, the Kristol family, Paul Wolfowitz, Harvey Mansfield, Richard Perle, John Podhoretz, Thomas Pangle, David Frum; while stating one should not leap to the unwarranted conclusion that all Straussians are neocons. Accessed June 3, 2007.
- Orwin C., "The Straussians are Coming!" The Claremont Institute, April 25, 2005. Accessed May June 4, 2007.
- Orwin C., "The Straussians are Coming!" The Claremont Institute, April 25, 2005. Accessed July 22, 2007.
- For example, this column against Michael Ignatieff and this column about education and technology.