Alcibiades
One of the greatest flip-floppers in all military history, Alcibiades was an ultimate example of serving his own interests above all else. He might be one of the least known of this list, but he absolutely deserves a spot for betraying his city three different times. During the great Peloponnesian War between Athens and Sparta, the born and raised Athenian Alcibiades commanded armies for the Athenians before defecting to the Spartans, then he defected to the Persians, and finally back to Athens.
Alcibiades was a brilliant general, both with his tactical ability and with trickery and diplomacy to take control of countless strategic towns in Greece during the war. He had a masterful grasp of strategy as well.
A planned Sicilian expedition was Alcibiades’ idea, and it could have led to a powerful Athenian base in Syracuse, but Alcibiades’ politic enemies kept that from happening. When he was accused of sacrilege, a serious crime in Greece, ships were sent to the fleet to bring back Alcibiades to stand trial.
Instead of following them back, Alcibiades set sail for Sparta, the sworn enemy of Athens. Many historians believe that the Sicilian expedition might have been a success if Alcibiades led it; without him, it was a failure that directly contributed to Athens eventual defeat in the war.
In Sparta, Alcibiades served in an advisory role. He told the Spartans to build a permanent fort near Athens instead of having a yearly campaign. The plan was genius. It kept the Athenians from harvesting their fields and prevented access to their immensely profitable mines while making them reliant on sea shipments for supplies.
Soon, however, Alcibiades found himself in trouble at the Spartan court. The King Agis’ new child was widely rumored to have actually been Alcibiades’ child after an affair with the Queen Timaia. Obviously, Alcibiades couldn’t hope to stay alive with such rumors floated around and so he fled Sparta just before men were sent by the king to capture him. This time he fled to Persia of all places.
Here though Alcibiades seems to have just focused on his return to Athens. After long negotiations, Alcibiades was able to get his original charges of sacrilege dropped and finally returned to his native land. Political strife struck once again, but Alcibiades was just removed from command instead of fleeing.
Alcibiades did have reasons for his betrayals, even if he did cause a lot of his own problems, such as in Sparta. His spot on this list, however, comes mainly from how much damage he did to Athens when serving Sparta. Athens would eventually lose the war, and a large portion of momentum was due to the strategies Alcibiades devised for the Spartans. According to the sources, he approached the Spartans and “promised to render them aid and service greater than all the harm he had previously done them as an enemy”. Certainly, the words of a traitor.