“Yes. It's about one of your youngest crew members. Crewman Shapiro's had a death in the family.”
“Oh, well, that's unfortunate, but I'm not following you.”
“You should tell him personally.”
“Can't his family?” Jonathan would do it but he didn't love such chores.
This bit in particular makes 'Jonathan' sound like an extremely unsympathetic, petulant child.
One of his crew's relatives has just passed away and when faced with the task of conveying this information, he whines "Can't someone else do it"
like a whinging teenager.
The "Oh well, that's unfortunate"
doesn't exactly come across as the most pleasant sentiment to come from the mouth a heroic, statesmanlike Starfleet captain either.