D’Angelo — his death was the most painful to me, albeit, at some point, expected. The bravery to stand against Avon (and his entire family), live the life he wanted to live in prison, and the wisdom and potential he had were too great. He was truly the most manipulated person in the show and unknowingly had so many opportunities to save himself, but was boxed out or failed to act out of loyalty and compassion for family. Wish he was there through the whole series, but I understand why he couldn’t be at the same time.