Part One: A soldier, Corp. Owens, is wounded on a look out mission. The battalion aid station calls the 4077th and has Radar bring choppers in Lt. Jack Mitchell, aka Smilin' Jack, picks up Lt. Owens and brings him to the 4077th. While Hawkeye works on Owens and Frank does anesthesia, Jack comes in to take a picure of him and flirt with the nurse. Jack says that if he takes a picture of his passenger, they live. Jack says Owens is his 839th passenger, and he needs four more to beat Dangerous Dan for chopper pilot of the year. Frank gets all upset over Jack's behavior, until Jack takes his picture and he smiles. Later, in post-op, BJ is going through the rounds and gets to Owens, who is asleep. Frank interrupts to present Owens with a Purple Heart, and is upset when BJ objects to interrupting Owens' rest. Col. Potter is in his office dictating a letter to a general apologizing for Hawkeye's behavior when the general visited the camp to Radar when Jack comes in to visit. Potter asks him to get some streptomycin and he trades for some after-shave lotion that he will give to the 8055th for them to use as specimen bottles. Jack gives Potter a Cuban cigar from MacArthur's HQ, but when he lights it, Potter notices a scar that he worked on several months ago that Jack said was where an Australian nurse scratched him. Potter gets suspicious as Radar comes back with the after-shave lotion. Later, Jack does his trick where he launches a syringe with a knife into an orange. He hustles a couple of club sodas out of Hawkeye and BJ. They get suspicious when he orders the club soda. BJ says he can do it, but the syringe lands in the wall by the door just as Potter comes in. He says that Jack got him for 17 one night, then orders Jack grounded and for the docs to give him a physical.
Part Two: Hawkeye and BJ give Jack his physical, but when they get to the urine sample, Jack objects. They give him a champagne bottle to use, because they are out of specimen jars. Jack starts to leave, BJ asks what Potter suspects, and Jack says that he has diabetes. He says that he needs insulin sometimes three times a day and that he gets it through his scrounging. He says that he was going to turn in his wings himself, but not until he beat Dangerous Dan for chopper pilot of the year. The doctors object, but Jack says no one is going to ground him. In post-op, Margaret says that Owens will be going back to the front and Frank says that he wishes he was going up there. BJ clears them out and Owens tells him that he doesn't want to go back. They start talking, but Radar interrupts to say that Jack has gone to pick up more wounded, so BJ has Radar talk to Owens. Potter and Hawkeye are in Radar's office as Potter tries to call Jack to get him to come back. BJ joins them as Jack replies that he is getting four to break the record. Owens tells Radar about what happens to him in combat. Potter tells about one pilot that he knew that flew low in WWI and dropped grenades on the enemy. He says that once the pilot had a grenade drop in his lap after the wind took it. He says that Jack could black out or have blurred vision while flying. He also says that to get four wounded, he would have to put two inside with him, besides the two on the rails. Jack gets the wounded safely to camp, and Hawkeye and BJ get him to give them his wings. He gives Potter the streptomycin and gets on the bus with Owens. Owens tells Radar thanks for the talk. However, just before Jack leaves, he sees Dangerous Dan bring two more wounded in.
Epilogue: In OR, Potter tells more stories about his pilot friend. BJ says that three wars gives him lots of stories and Potter says too many. Hawk asks which one was the worst. Before he can answer, the PA says that an English regiment lost all but 100 of their 600 men. Potter answers Hawkeye, 'Each and every one, Hawkeye. Each and every one.'