Loki already won, with the wincoin being for him that he could return Harald to his senses. It´s what Gaban failed to do, and believed that much of the world would struggle with.
The idea of turning Harald back to his senses was hopeless to him. Do you not understand the specific context here of why Harald let himself be killed, or do you believe it´s because he was stronger then Loki? If not, the fixation of Harald letting himself be killed is just copium.
He did have some help against Kaido yeah. Yamato pointed out he was already getting exhausted, current Luffy is still a bit weaker IMO.