Well after Chuckie was clipped, remember that Jack walked over to Chuckie's house with a pot of flowers for his widow and said "Laura it was me, I ordered it and I'm sorry."

Being Al Capone's son, I can say its fairly common for mob guys to share details of why they were hit with their wives. That conversation usually happens in the morgue.

And continuing to openly associate with the man responsible for your family member's murder? Ha! What is this? The mafia?