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I'm gonna say his 2nd run. He was always booked in dream matches that exceeded expectations. And when he wasn't booked in dream matches, he took the "meh" looking matches on paper, and made them MOTY candidates.
So I guess the deciding factor for me was that his "legendary status" in his 2nd run allowed him to be booked in those "dream matches" that made for a lot of great moments/matches, since he took those "meh" matches and made them amazing throughout his entire career.
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