Nately tells Yossarian he wants to fly more combat missions, even though he already has 70; if he stops flying he’ll be sent home, and if he’s sent home, he can no longer see his girlfriend, the prostitute in Rome. Yossarian can’t believe Nately wants to stay in the combat zone.
Once again, although Nately’s idea seems crazy—who would want to fly more missions?—he has a perfectly rational reason for wanting to stay near Rome, where his girlfriend resides.
Milo has also been asking Cathcart for more missions. Milo, who has spent the past few months building his business, M & M Enterprises in large part by selling goods to the Germans, decides he wants to do more to “help the war effort.” He tells Cathcart he has only flown five missions, but Cathcart says Milo’s work with M & M has been important and noteworthy, despite Milo’s lack of combat missions.
Milo’s desire for more missions is less straightforward, however, as his interaction with Cathcart will prove. Cathcart loves the goods that Milo brings to Pianosa so much, he is willing to suspend Milo’s combat duties in order to ensure steady delivery of items like melons and bananas.
Cathcart admits he’s only flown two missions himself—and the men in the group know this. Milo pretends that he is willing to take on an enormous number of new missions, and he begins explaining the complexities of his cartel to Cathcart, who initially believed he could take over for Milo in running M & M Enterprises while Milo was flying his missions (and perhaps reap some of the profits as well).
Interestingly, and hypocritically, Cathcart has barely flown any mission at all, though he feels comfortable sending his men into harms way on a constant basis. Cathcart is also greedy—he would love to make a little extra money, via the cartel, on the side.
But the cartel proves so complex that Cathcart cannot begin to understand it. Cathcart instead tells Milo that, since he is needed to run M & M, he, Cathcart, will get someone else to fly Milo’s missions for him. This was what Milo wanted the entire time—he fooled Cathcart, but Cathcart doesn’t understand the trick, and even promises that Milo will receive any heroic citations earned by the men flying his missions in his place.
Despite all the time he spends cooking up stratagems of his own, Cathcart has a hard time understanding the true motives of those around him. This is also true of his interactions with Korn, who appears to get the better of Cathcart on most occasions, although Cathcart considers Korn uneducated and stupid.
One of these ensuing missions, over La Spezia, is flown by Dobbs, and Nately, among others. They encounter heavy flak and are shot down by Germans defending the port. No parachutes deploy, and Dobbs’ plane crashes into the water. No parachutes are released. Dobbs and Nately, along with others, are killed.
Heller characteristically narrates the death of Dobbs and Nately without much ceremony. He does so to indicate just how quickly soldiers, part of the life of Pianosa, can disappear or die during combat. Their lives as soldiers are tenuous.