History
Not very much is said of Yossarian's past. Events before he joined the Army Air Force are vague, only occasionally mentioned in passing. In fact it's not until the sequel, which takes place fifty years later, that it even mentions that one of the main reasons he'd joined was to have the money for college. The bulk of his story takes place in the present, and the before and after are left largely in the shadows.
Yossarian joins the Army Air Force and enters cadet school with the hope that WWII will be over by the time he finishes. This doesn't work out quite the way he'd planned it, and he's sent overseas in 1943. At this point, the standard number of required missions for a full tour of duty is 25, and once a man has flown that man he can be rotated back home again. However, in September, the current Colonel is killed on a mission, and Colonel Cathart takes his place. Colonel Cathcart is very concerned with looking good to his superiors, and takes it upon himself to ask his men for 30 missions instead of 25. This is Yossarian's first encounter with the rule of Catch-22: he doesn't have to fly the missions, because headquarters only asks for 25, which he has already finished. He does, however, have to do what Colonel Cathcart asks him to do, or he risks insubordination. It leaves him with no choice but the fly the missions, even though he doesn't have to.
Between September of 43 and May of 44, the missions are raised to 40. Two of Yossarian's fellow officers are killed when, on a mission to Ferrara, none of the squadron's bombs manage to bring down the bridge they'd been trying to destroy. Yossarian takes the flight back around again, successfully hitting the bridge this time, and it's on this second round that the plane next to his goes down. Colonel Cathcart and Captain Black can't understand when he gets back to the base why he'd take the crew around again, and he explains that if he hadn't, they'd have had to have gone back another time. Perhaps there would have been no losses on a return trip, Cathcart suggested. Maybe there would have been more, Yossarian returned. Why couldn't you just have gone around once and come back? Cathcart wanted to know. The bridge would not have been destroyed, Yossarian answered. Captain Black suggested that they give Yossarian a medal for having gone back again, and act proud of something they ought to be ashamed of. And promote Yossarian to Captain while they're at it, just to make sure. Cathcart agrees, and Yossarian becomes Captain Yossarian.
By the end of the month news is in the air that their next mission, to Bologna, will be a lethal one. Rumors about the artillery they have there run rampant, and the men are terrified. To make matters worse, the mission keeps getting delayed. First the entire squadron comes down with food poisoning, thanks to Yossarian and well-placed dish detergent, and then the rain won't let up. They get so far as taking off a few times before they get reports that the target is covered in clouds and are forced to turn back. The men are never quite sure whether they should be relieved or anxious for having put it off for yet another day. Yossarian finally moves the bomb line on the map at night, making it look as though their own forces have already captured Bologna, and the news travels all the way up the ranks, each man believing it and passing it on as fact to his superior. This good news can't last forever though, and eventually the error is realized and the mission is on again.
Finally the rain clears, the airstrip dries, and the men can't escape flying to Bologna. They take off, full of dread, and Yossarian promptly unplugs his headset. Unable to hear the rest of the crew over it, he has them turn the plane around due to faulty equipment. It's with something somewhere between joy to be alive and shame to have left the other planes to their fate that Yossarian's crew touches down again.
When the flight returns, it's with no damage, no wounded, and all planes intact. Yossarian first thinks that they'd had to turn back again and he'll have to fly it again tomorrow, but then realizes that they'd made it, they'd dropped their bombs, and there had been absolutely no return fire. It had been easy, a milk run. And so when their Colonel volunteers the crew to run the mission again the men confidently leap into the sky, start toward the target -- only to find themselves surrounded by flak. Bologna is better prepared this time, and it's all they can do to make it out alive.
The next mission is to Avignon in June. The plane is being rocked by flak, and Dobbs the pilot comes onto the headsets, yelling for them to help the him! Help the bombardier! He doesn't respond! Yossarian tells him that he's the bombardier, he's alright, and Dobbs sobs and tells him to help the gunner! Yossarian crawls to the back of the plane, where he finds Snowden, a young man, lying on the floor of the bomb bay with a chunk the size of a football out of his leg. Yossarian works as hard as he can, stripping away the flak suit to take care of the wound, bandaging it as best he can and telling Snowden that it's alright, he's going to be alright. Snowden keeps whispering to Yossarian that he's cold, he's so cold, and Yossarian works harder and tells him that it's alright. It's not until he's completely done that he notices a stain on the stomach of Snowden's flak suit. He unzips it, and Snowden's innards fall out. Snowden whispers that he's cold.
After they'd landed again, Yossarian stripped off his clothes, covered in Snowden's blood. He chooses not to put his clothing on again, because they're still, in his mind, bloody. He attends Snowden's funeral in a tree across the field, still naked, and no one can manage to make him put any clothing on until the unit is standing in formation and a general arrives to award a medal to Yossarian for his bravery at Ferrara for going around twice, only to find that there's no shirt to pin it to. This is Yossarian's first introduction to the upper ranks of the Army, and the point at which he'll be taken.