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Milo is first mentioned when Yossarian has dinner after being released from the hospital. We learn that Milo runs the mess hall and provides it with good food.
Milo meets Yossarian and is impressed by his business savvy with the fruit episode. He wants to form a partnership, but Yossarian refuses.
But Milo entrusts Yossarian with all his secrets anyway.
We learn that Milo lives by a strict set of morals, but that his morals allow him – even require him – to charge the highest prices possible. But they won't allow him to borrow a package of pitted dates from the mess hall because they're government property.
He can, however, borrow the same package of pitted dates from Yossarian and even trade it as McWatt's interest to a thief with a sweet tooth who stole McWatt's bed sheet from him that morning, and then get both the dates and bed sheet back.
Milo takes a quarter of the bed sheet "for the syndicate," gives half back to McWatt, and a quarter to Yossarian, along with the dates.
We find out that Milo's life goal is to open a mart (like a store).
When Major Major is promoted, Milo sets up a private table for him in the front of the mess hall.
Milo approaches the intimidating Major -------- de Coverley with fresh eggs. The Major is so impressed that he immediately assigns Milo mess hall duties.
During a rest leave, Milo flies with Yossarian to Cairo on some business.
Milo takes them from Pianosa to Sicily to Palermo. At each stop, he keeps promising Yossarian and Orr a nice hotel room with prostitutes where they can relax. They never get these hotel rooms because Milo keeps abandoning them for new projects.
Upon arrival in Palermo, we learn that Milo is mayor there and treated like a celebrity. His barber tells him of an upcoming artichoke auction, and Milo takes off to try to make a profit.
The rest of the trip is similarly frustrating. Milo seems like an official in every city they stop in, and everywhere they stop, he goes off to buy or sell something. All his profits, he claims, go toward the syndicate, though his methods for making said profits are dubious.
They fly from Palermo to Naples to Malta to Oran to Cairo. In Cairo, Milo buys Egyptian cotton and green red bananas.
At last they head back to Pianosa. Neither Yossarian nor Orr has found their rest leave the least bit relaxing.
Milo gets army planes for transporting his produce and repaints them with "M & M" emblems.
Milo is indignant when he returns with German bombers full of produce and meet a squad who wants to arrest the Germans and confiscate their planes. Milo defends them as shareholders in the syndicate and the squad backs down. All in the name of capitalism.
Milo plans attacks on American bases using German planes. He profits from them.
Yossarian confronts Milo about Mudd, who died because of Milo's traitorous mission.
Milo refuses to accept the blame for Mudd's death.
Milo bombs the Pianosa base for money and is almost taken down by the American press until he reveals how much profit the syndicate has made. Again, this gets him off the hook.
During Snowden's funeral, Milo asks a naked Yossarian to try some chocolate-covered cotton. He is desperate to get rid of his excess supply of cotton.
Even when Yossarian tells him the cotton is inedible, he persists. Yossarian suggests Milo bribe the government to buy the cotton from him. Milo initially balks at the idea of bribing the government, then is convinced by the promised profits.
During the Marseilles and Avignon missions, Milo removes key survival gear from the planes to fund his own food enterprises. He leaves apology notes saying what's good for the syndicate is good for everyone. Both missions end in disaster.
Milo convinces Colonel Cathcart to forbid him from flying more combat missions because he needs him to run the syndicate.
However, they arrange for others to fly Milo's missions and for Milo to get the credit. They also simultaneously opt to raise the number of missions to eighty.
On a rest leave to Rome, Milo berates Yossarian for refusing to fly more missions. Yossarian doesn't listen to him.
Milo agrees to help Yossarian look for the twelve-year-old kid sister of Nately's prostitute but ends up getting distracted by a possible profit in illegal tobacco. So he abandons Yossarian. Again.