I think when his brother died. His soul died with him
Yep. at that point he was pretty much dead inside (with the whole, "i would tell you to go to hell, but i think your already there" line that Ethan Hawke said near the end) as everything he cared about was completely gone.
he was dead to his mom/dad, his brother was dead, his wife/son left him and he basically triggered it all by taking his bro with him on one last job and he was lying to his wife and especially when that painting she done was supposedly sold to some 'anonymous rich buyer' type thing and she knew he even lied to her about that. it just pushed her over the edge and she left as their marriage was basically a lie.
at that point all he had left was the job itself.
that pretty much sums up the emotionless question the OP asked. he was just so cold and his soul was running on empty at that point. it was probably difficult for him to even cry etc.
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