Milo Minderbinder and ex-P.F.C. Wintergreen

Milo Minderbinder and ex-P.F.C. Wintergreen are the two most influential non-commissioned operators in the Mediterranean theater, and their shifting relationship—from covert rivalry to outright merger—exposes the novel's central argument that war, bureaucracy, and capitalism have fused into a single self-serving system. Wintergreen, a mail clerk at Twenty-seventh Air Force Headquarters, controls the flow of official correspondence and wields a mimeograph machine; Milo, the mess officer turned international syndicate chief, controls the flow of food, goods, and airplanes. Their alliance, when it finally comes, is less a friendship than a corporate consolidation that leaves no institutional force able to oppose them.

Rivalry and Mutual Undermining

Wintergreen first appears as a decisive force when he throws General Peckem's prolix communications into the wastebasket, thereby handing General Dreedle a victory in their jurisdictional dispute over tent-pitching. Wintergreen finds Peckem's prose "too prolix" and prefers Dreedle's less pretentious style, so he speeds Dreedle's views along in "zealous observance of regulations." This act establishes Wintergreen as a gatekeeper who can make or break careers by the simple act of discarding or forwarding paperwork. Milo, meanwhile, is building his syndicate by buying eggs in Malta for seven cents and selling them in Pianosa for five cents—a paradox that Wintergreen immediately grasps and mocks. When Yossarian tells Wintergreen that Milo is selling Zippo lighters for a dollar and a penny, Wintergreen snickers triumphantly: he sells his own stolen lighters for a buck apiece. "I beat him every time," he gloats. Wintergreen also taunts Milo about the Egyptian cotton disaster, calling him "a dope" for buying the entire crop. Milo, in turn, complains that Wintergreen "has no respect for rules and regulations and keeps cutting prices on me." Their competition is personal and commercial, but it never escalates into open warfare because both recognize the other's utility.

Shared Methods and Moral Flexibility

Both men operate through a combination of bureaucratic manipulation and black-market entrepreneurship. Wintergreen, when asked by Yossarian to forge official orders to cancel the Bologna mission, refuses on principle: "It's your job. We all have our jobs to do." Yet he is perfectly willing to steal Zippo lighters from quartermaster and sell them at a profit. Milo, for his part, bombs his own squadron under contract with the Germans and then justifies it by disclosing the net profit. When Yossarian suggests Milo bribe the government to buy his Egyptian cotton, Milo is initially outraged—"Bribery is against the law"—but immediately asks, "How will I know who to bribe?" Both men treat morality as a flexible instrument, not a fixed constraint. Wintergreen's signature act is to distort, destroy, or misdirect any correspondence that might do Colonel Cathcart credit, thereby blocking Cathcart's promotion. Milo's signature act is to turn every military operation into a profit center, including the bombing of his own men. They are mirror images: one works through information, the other through goods.

The Merger and Its Implications

By the novel's end, the rivalry has been superseded by a merger. Major Danby tells Yossarian that "Milo and ex-P.F.C. Wintergreen merged last week. They're all partners now in M & M Enterprises." This consolidation eliminates the last institutional check on either man's power. Wintergreen, who had risen to ex-corporal and then been busted back to private, now has a stake in the syndicate that controls the entire theater's food supply, transportation, and even combat missions. Milo, who had been vulnerable to Wintergreen's price-cutting, now has the mail clerk's mimeograph machine and information network at his disposal. The merger means that no official report, no promotion, no supply chain can function without passing through their combined apparatus. As Danby laments, "There is no hope for us, is there?" The answer is no: the two most resourceful manipulators have joined forces, and the system they have created is now self-sustaining.

Thematic Significance

Milo and Wintergreen's relationship embodies the novel's critique of how wartime institutions are hollowed out from within by private enterprise and bureaucratic gamesmanship. Wintergreen, who "wanted to be a general" and who "always distorted, destroyed, rejected or misdirected any correspondence by, for or about Colonel Cathcart that might do him credit," is the hidden hand that shapes the war's official narrative. Milo, who declares that "the business of government is business" and who treats every contract as an opportunity for profit, is the hidden hand that shapes the war's material reality. Together, they represent a fusion of information control and economic control that renders traditional authority—generals, colonels, even the War Department—powerless. Their merger is the logical endpoint of a world in which Catch-22 has become the only law: a law that exists nowhere in writing but is enforced everywhere, a law that says those who control the flow of information and goods can do anything they cannot be stopped from doing.