Representing an extreme version of capitalist free enterprise that has spiraled out of control, Milo seems simultaneously brilliant and insane. What starts out as a business in black-market eggs turns into a worldwide enterprise in which, he claims, “everyone has a share.” At first, Milo’s syndicate seems like a bit of harmless profiteering; we cheer for Milo because he is at least making money at the expense of the ridiculous bureaucracy that perpetuates the war. Like Yossarian, he bends the rules toward his own benefit; his quest for profit seems logical compared to the way Colonel Cathcart sends his men to their deaths just so he can get a promotion. All the men seem to like Milo, and they are perfectly willing to fly him to places like Malta and Egypt so that he can buy and sell his goods.
Milo’s racket takes on a sinister air, however, when he bombs his own squadron as part of a deal he has made with the Germans. Many men are wounded or killed in this incident, and Milo’s syndicate suddenly seems like an evil force that has expanded beyond anyone’s ability to control it. But Milo’s reasons for bombing the squadron are no more arbitrary than Colonel Cathcart’s ambitiously volunteering to send his men to dangerous Bologna. In fact, one could argue that Milo’s actions are more rational than Cathcart’s, since Milo is guaranteed a profit, whereas Cathcart does not really have a chance of becoming a general.
In many ways, Milo’s character shows how capitalism transcends political ideology. We are never given any idea of what the war is being fought over, and the men have no sense of defending the ideals of their home country. Milo’s ability to make money off of both friend and enemy, and his willingness to support whichever is more profitable, take advantage of the complete lack of ideology in Catch-22. Furthermore, his willingness to allow his own camp to be bombed shows his complete disregard for the sides drawn by the war, and the men’s acceptance of payment for being bombed shows that Milo is not alone in placing a high value on making money.