"Me and Sam.. it's always been hard for us. We fought from the time he was a teenager right up until the day I died." John had bitterly regretted not saying goodbye to his youngest, but he had been afraid. He had failed Sam so many times in the past, Dean had to be the one to survive and look out for his brother.

"I wanted to do right by him; to make him ready for what was coming. I had an inkling of what the demon's plans were for Sammy. I pushed him too hard, I pushed them both too hard. When he left us to go to college, I let him go. I didn't go after him, even though I wanted to. I thought if he had a chance at a normal life, he deserved it. It was all he ever wanted and I couldn’t give it to him.”

John drained his glass in one swallow, savoring the burn. He loved his sons fiercely, but he had been a damned coward. “I should have told them everything.”

The elder Winchester shook himself and raised his eyes back to Castiel and his offer. “No. Sam gave it to you for a reason. If he wanted you to wear it, then please, keep wearing it.”

Sooner or later, he was going to have to talk to both Sam and Dean. He couldn’t make up for past mistakes, but he could at least attempt to apologize to them.