The relationship between Alexander the Great and Aristotle, one of the most famous teacher‐student relationships of all time, was in fact not a peaceful or cordial one. Behind the Unverifiable story of Aristotle poisoning Alexander, lies some more profound differences between these two in terms of their values, perspectives, and philosophies. By analyzing ancient sources by writers such as Arrian, Plutarch and Diodorus, this essay illustrates Alexander the Great's and Aristotle's different opinions on the treatment of conquered peoples in an empire, and seeks to bring about a deeper understanding and appreciation of Alexander's multiculturalism.