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Jack writes in a diary, but instead of titling it like others would with "Dear Diary" He directs each entry to a different Newsie. He finds it easier to let it all out if his mind thinks he's writing all this to somebody. His diary entries are really more like letters he'll never send.
Dear Racetrack,
We got some new kids today, Davey and his brother Les. Les thought I was pretty cool, Davey might take a little more convincing. They seem pretty sound though, they got parents and a flat, the whole nine yards, y'know?
Dear Jojo,
We're officially on strike against Pulitzer! That bastard raised the prices without even a word of warning to us and expect us to just go along with it? Yeah, well, have we got news for them, am I right?
Dear Crutchie,
This wasn't how today was supposed to end. I know we were warned this could go wrong, but I didn't think we'd be beaten that badly.
I feel like real shit knowing I didn't go down there and help him after all those times he helped me. My brothers been sent to the one place I swore to protect everybody from, and I just stood there. I'm so sorry Crutch.
Dear I'm sorry I let you down Davey.