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Little Sonic 3 yapping up ahead:
I can't stop thinking about how Shadow knew he inflicted the same pain on Sonic that he felt when Maria died.
He felt reassured in Sonic's rage, wanted him to understand that that is how he feels but mostly he wanted Sonic to be able to get his revenge.
He was ready to give his life for Sonic to get the revenge he himself sought for. He thought the world would end eitherway and was ready to give up on witnessing the demise of those he blamed for his loss. Because he saw himself in Sonic. Because he felt sympathy for him. He wanted to give Sonic the revenge he sought for before everything ended.
He kept making Sonic more mad to see that he would reacted the same. To prove to him he was doing the right thing. But Sonic didn't. Sonic realized he was doing the wrong thing and soon so did Shadow