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This paper is inspired by the sentiments of Winston Churchill, “The further back you can look, the farther forward you are likely to see.” Notwithstanding all the work and intellectual efforts by current scholars and practitioners on the topic of good leadership and good character, there is much to be learned by drawing from the ancient philosophical tradition, notably Socrates, Plato and Aristotle. Simply said, it is critically important that we learn from and apply the wisdom of the ancients to the current thoughts and practices as to how character and leadership are acquired and developed. The timeless wisdom of the ancients is even more relevant today given the ever-increasing pace, complexity and uncertainty faced by individuals, organizations and societies. We claim that Aristotle’s rich discussion of what virtuous (good) character is, and how it is acquired is extremely relevant to contemporary scholarship in leadership studies, and can cast valuable light on three questions: 1. Why is the connection between leadership and virtuous (good) character important? 2. What is (good) leadership and (good) character? 3. How do we acquire and develop both of these attributes? Our thesis is that Aristotle’s account of virtue helps to explain the deep connections between good character and authentic leadership… and leadership (of both self and organizations) with purpose.