She's talked about the arena a little. He barely understands it but from the bits and pieces he's picked together from the many people he knows here from that world, it's some sort of barbaric fight to the death for the sake of public entertainment. Even a pirate can't quite fathom why the public would be entertained by such things. He knows enough about Cashmere now that he does not suspect that simply going back into the arena had set her on a tailspin, and in the end he's right.

Hook isn't sure there's a right or wrong in a situation where everyone is pitted against each other an a desperate bid to survive. Is the right thing really to die? If it is, then he'd have been just as wrong. What he can relate to, though, is the broken I couldn't— because that he knows, and that he understands, and he knows full well that hurts a hell of a lot more than the wound she took herself.

"When my brother died, it all happened so fast. Nothing I could do." He's not spoken of his brother in some time, and even with David he'd neglected finer details. "Even three hundred years later I still wonder why I wasn't strong enough to save him." He chugged back the wine, because Cashmere is his friend or as close to it as the pirate can get anymore, and inquires, "And that's it?"

It sounds a bit callous, but it's a bland way of inquiring if she really dies. The girl in the hotel told him as much, but he wants to hear it again anyway.