Milo continues expanding the reach of his black-market smuggling business, “the syndicate,” explaining to various officers across the Mediterranean that he only needs the use of some of their planes to get tangerines, melons, and other exotic goods. General Dreedle, who enjoys eating Milo’s food, supports this plan, and demotes officers who don’t comply with Milo’s requests.
Like Cathcart, Dreedle greatly enjoys all the foods that Milo manages to bring to Pianosa. Dreedle is willing to sacrifice men and material in order to satisfy his tastes—clearly a diversion of military strategy and men's lives for his own ends.
The syndicate, now termed M & M Enterprises (for “Milo” and “Minderbinder”), begins doing business behind enemy lines; it then uses Axis planes to transport items. Some US Army officials complain that this is consorting with the enemy, but Milo effectively combats them by arguing that he is only doing business, and doing business is the American way. And, he adds, everyone gets a share in the company’s profits.
Milo turns a commonly-used American justification for capitalism on its end. He argues that consorting with the enemy must be patriotic if it is done for the sake of profits—for profits are the American way. Again, it is not clear that these profits actually exist, but Milo makes a convincing case to his commanding officers. And the officials' greed lets him get away with it.
Milo begins actively supporting German military activities: he orders US planes to bomb a bridge near Orvieto and German guns to shoot at those planes, all for the sake of defending his merchandise. Yossarian argues that this, surely, is treason, but Milo counters that only his business contracts matter, and that upholding them is patriotic and American.
Milo now clearly dips into treasonous territory. Heller often allows his descriptions of Milo to veer into caricature—it is of course not possible to imagine that this behavior could exist in the real military, but in its exaggerations Heller is making a real point about those who seek to profit from war.
Milo has purchased all the cotton in Egypt, but there is no market for it, and his company verges on collapse. He then orders his planes to bomb the American’s own base on Pianosa, in order to deplete their supplies of material and aid his own business interests. None of the soldiers can believe what’s happening, but Milo wins back the support of the group by repaying them with profits from the cartel, and by arguing that war itself should be privatized—the government should be “cut out”—so that profits can be distributed among the citizens who fight the wars.
The pinnacle of Milo’s treasonous activity. What could be more anti-American than actively thwarting your own military’s base. Heller appears to be making a commentary here on the tendency of capitalist profit-interests to override concerns for country, safety, and security, Milo again uses pro-capitalism arguments to justify his actions as patriotic.
Doc Daneeka tends to Yossarian after Milo’s bombing of the group. This reminds Yossarian of the way Doc Daneeka treated him, with great care, after the Snowden incident over Avignon. (Time in this section becomes hard to disentangle—it appears that Milo’s growth of M & M has coincided with the bombings over Avignon, in which Snowden was killed.)
The bombing of the Pianosa camp, which does not appear to generate any deaths or serious injuries, nevertheless reminds Yossarian, once again, of the Snowden incident, which begins recurring in these chapters even more frequently than before. It seems that Yossarian’s nerve for battle is fraying.
The Avignon bombings, as stated previously, cause Yossarian to undergo a “break,” and he refuses to wear his uniform. He climbs a tree during Snowden’s funeral, out of grief, and Milo climbs up with him to talk to him.
The vision of Yossarian in the tree is an important one in the novel, noted by many, including the chaplain and Cathcart. Interestingly, neither recognizes the man immediately as the Yossarian they know.
It is revealed that Milo’s simultaneous bombing and defense of the bridge at Orvieto resulted in the death of the “dead man,” Mudd, in Yossarian’s tent. Yossarian argues that Milo is responsible for this, but Milo counters that these deaths are fated, and that he is merely doing business the American way. Only Yossarian seems perturbed by Milo’s willingness to consort with the enemy. He remains in the tree during Snowden’s funeral.
It turns out that Milo’s earlier military action in Orvieto is the action that killed Mudd. Thus Yossarian has every reason to hate and distrust Milo, for a series of actions that resulted in the loss of American lives. But Milo is so convincing a salesman, he does not allow his fellow men to be angry at him for very long.
The chaplain sees a naked man in the tree, while performing Snowden’s funeral service, and wonders who it could be. Milo mourns his terrible financial situation—he is overburdened with Egyptian cotton—and vows to fight for his syndicate’s survival.
Here the chaplain notices the naked man and wonders if he is some kind of symbol—although he does not know what of, or who put that man in the tree in the first place. The chaplain is at this point struggling with his faith, and so the chaplain's attempts to interpret this ambiguous symbol in a tree is an apt way of capturing the chaplain's own search for meaning.
Yossarian suggests that Milo bribe the US government to buy all this cotton at a low price. But Milo is offended: he claims that bribing is against the law and immoral. With that said, he realizes that “the business of government is business,” meaning it is acceptable to sell private goods to the government. He feels there might be hope for his syndicate after all. As the two leave the tree at the end of the funeral, Milo tells Yossarian to put on some clothes—otherwise soldiers will start going naked, and demand for cotton for uniforms will decrease, hurting Milo’s business.
This is where Milo draws the line. It is of course acceptable for him to bomb his own base, and even to kill some Americans, for the sake of profits. But to offer a bribe is to “break the law.” Here Heller satirizes business interests that appear to draw strange ethical boundaries in search of more money.