How to interpret 'when' in this sentence?

Question

I have a question about how to interpret 'when' in the bold-lettered sentence. Below is the context and the sentence (from Beginners by Raymond Carver).

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“It gets worse,” Terri said. “He shot himself in the mouth, but he bungled that, too. Poor Carl,” she said. She shook her head.

“Poor Carl nothing,” Herb said. “He was dangerous.” Herb was forty-five years old. He was tall and rangy with wavy, graying hair. His face and arms were brown from the tennis he played. When he was sober, his gestures, all his movements, were precise and careful.

“He did love me, though, Herb, grant me that,” Terri said. “That’s all I’m asking. He didn’t love me the way you love me, I’m not saying that. But he loved me. You can grant me that, can’t you? That’s not much to ask.”

“What do you mean, ‘He bungled it’?” I asked. Laura leaned forward with her glass. She put her elbows on the table and held her glass in both hands. She glanced from Herb to Terri and waited with a look of bewilderment on her open face, as if amazed that such things happened to people you knew. Herb finished his drink. “How’d he bungle it when he killed himself?” I said again.

(From Beginners by Raymond Carver)

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Ok. Here is the situation. There are four people. Terri & Herb, I(the narrator) & Laura. They are married couples. They are talking about love, real love. And Terri started talking about her last lover. This guy, Carl, obviously was very obsessive, used violence, and when Terri finally left him, he drank rat poison. And when that failed, he tried to kill himself by shooting himself in the mouth. But he didn't die instantly, lived for three days (this fact was not said yet, Herb was going to say it shortly, but he did say that Carl is dead).

Now, what I want to know is how to interpret "when" in the bold-lettered sentence. Should it read like this?

1. How did he bungle it while he was trying to kill himself? (e.g. I want to know how he bungled while he was trying to kill himself.)

Or, like this.

2. What do you mean he bungled it when he killed himself and died(so succeeded in doing it)? (e.g. I want to know what you mean he bungled it, didn't you say he's dead?)

Answer 1

A very contextual question. It is clear that at the time of the quoted conversation, Carl had shot himself.

The use of "when" is a contrasting mechanism of the form: "Why is something A when (we also perceive it as) B?"

A bungle means that the intentions were not fulfilled in some way. If we assume no knowledge of the following context (to be revealed later by Herb), the narrator is posing the question in ignorance of the details of the death. The narrator therefore asks in what sense this was a bungle, because all the narrator knows is that it was a successful suicide and therefore seems not to be a bungle.

On the other hand, if we include the later following context (revealed by Herb) that Carl died in such a manner as to not die instantly but taking three days, then his intention was to kill himself but it is not believable that he wanted to do so in such a painful and protracted manner. This was therefore a clear and evidenced bungle in the method of suicide; the narrator would not need to ask about it. Hence we would exclude your first possibility. The narrator is therefore asking about the main intention and outcome rather than the secondary details. If Carl intended to kill himself, and did so successfully, why would we consider this a bungle? By using "when", the narrator is contrasting the intention with the outcome and asking the rhetorical question "why is this a bungle?" so as to make the point that the suicide was both intentional and successful.