We have two pieces of advice for you, Shmooper: never get involved in a land war in Asia, and never go in against Ulysses when death is on the line. Because he is going to totally out-trick you.
Ulysses didn't earn his epithet "crafty" for nothing. Tradition has it that this is one smart guy. But in Troilus and Cressida, he's more than just clever—he's downright manipulative.
After all, he's the guy who comes up with the scheme to rig a fake lottery so the top warrior (Achilles) will be jealous of Ajax when Ajax is sent to fight Hector in man-to-man combat. (Technically Achilles should be the one to face Hector because he's the Greeks' top warrior.) Ulysses even brags "I have a young conception in my brain, / Be you my time to bring it to shape (1.3.312-313). What's crazy is that Ulysses hatches this plot just mere moments after delivering a big, fancy speech about the importance of social hierarchy and respect for authority (1.3.75-137).
Why does this matter? Well, literary critics like to remind us that Ulysses embodies something called "Machiavellianism," which is a cutthroat style of political leadership that was popular but controversial in Shakespeare's day. The term comes from the name of an Italian philosopher and poet, Niccolò Machiavelli. Machiavelli wrote a famous book called The Prince (1532), which is basically a self-help guide for rulers who aren't afraid to break a few rules—or heads.
According to Machiavelli's theory, being a successful leader has nothing to do with being a nice person or doing the right thing. Instead, it's about being inventive, manipulative, charismatic, crafty, and willful. Hmm. Sounds just like Shakespeare's Ulysses, don't you think? The guy is basically the evil genius responsible for all of the Greek's military and political moves. In fact, Ulysses isn't Shakespeare's only Machiavellian villain. Check out our analyses of Prince Hal and Richard III for more about that.
Like we said earlier, Ulysses is the guy who gives one of the play's most famous speeches about the importance of social order and how the world will totally fall into chaos if people step out of line. (1.3.75-137). Yikes! You can read the whole thing here.
In the past, literary critics have argued that the speech sums up Shakespeare's and the Elizabethans' attitude toward social hierarchy. In short? Social hierarchy rocks, and everyone should just chill in their God-given place.
But you know what? Just because Ulysses gives a speech about it doesn't mean that Shakespeare actually believes any of it. Plus, it's not clear that Ulysses believes it either. About two seconds after Ulysses gives the speech about how everyone should obey the special pecking order, he goes out and sends a second-string soldier (Ajax) to fight Hector when he knows that he should send the Greeks' #1 warrior (Achilles) instead.
So. Grand statement of social philosophy—or just another sly trick in Ulysses's bag? You decide.