Milo is a man with a brilliant talent but no conscience. Initially a friend of Yossarian's, the mess officer is a genius as an entrepreneur, creating a syndicate that controls the black market. But as a human being, he is almost exclusively interested only in his own best interests.
Milo is masterful but corrupt, parlaying his position as mess officer (in charge of the dining hall) into personal direction of M & M Enterprises, controlling all sorts of goods and services, from fresh eggs to prostitutes. Before long, his business is international; planes arrive daily from such markets as Liberia, London, and Karachi. He deals with everyone except the Russians, eschewing their trade because they are Communists. Nonetheless, he has no problem doing business with America's primary European enemy, Nazi Germany. Milo even profits from specific battles. When the Allies plan to bomb a highway bridge at Orvieto, Milo arranges to conduct the attack for them. But he also agrees with the Germans to defend the same bridge with antiaircraft fire, bargaining for cost plus six percent from each side, plus a "merit bonus" of $1,000 from the Germans for each plane shot down. Having arranged all the details, Milo has no trouble convincing both sides to furnish their own men and equipment. He thus makes a nice profit by signing his name twice. This is the raid on which Mudd, the "dead man" in Yossarian's tent, is killed. Even more despicable than the Orvieto deal is Milo's arrangement with the Germans to bomb his own squadron when the syndicate's cash flow runs low, due to excessive investment in Egyptian cotton. This time it appears that Milo may have gone too far. Newspapers and politicians back home denounce the attack on American airmen. Heller's satire is especially biting as he points out that all is forgiven after Milo demonstrates that the raid turned a healthy profit. Milo concludes that all wars should be conducted by private enterprise — so long as the governments pick up the expenses. For Milo, the chief business of the American people should be business: his business. A contract is a contract — so long as it favors Milo. Milo likes to say that everyone owns a share of M & M Enterprises, but Milo seems to take most of the profits.