He was crying for Chuck bc they were close, it was the way that Winston died and the realization of how that shows on his face, he was in shock for Newt bc of the way Newt has to die, and Teresa was one of the only things he had left and she was almost saved but then she fell.
Life asked Death, Why do people love me, but hate you? Death responded, Because you are a beautiful lie, and I'm a painful truth. A truth we must all face. So why be afraid of it? Live life fully cause we never know today may be the last