Alright I'll try my best. Dredgen Yor was once a great hero, a hunter and a Gaurdian. His prized Hand Cannon was called Rose, but his prize had a dark secret. It corrupted Yor and the darkness consumed him, causing him to murder other guardians.
Jaren Ward was also a hunter, and one with another prized hand cannon. The Last Word. One day he went through a town with his crew, where he met a young man named Shin Malphur. Shin was captivated with Jaren's Hand Cannon and became his apprentice.
At a time, and at a place called Dewindlers Ridge, Dredgen Yor faced Jaren Ward. However, Yor came out triumph and murdered Jaren. When Shin learned of his mentors death he went to avenge him. He acquired the Last Word, and with it, he killed Yor in two shots (clearly pre 2.0.0).
At this point it's speculation, some day it was a Golden Gun but the Griomore talks about using his third fathers cannon (Last Word). Some also believe that Yor was struggling internally with his morals and letting the darkness corrupt. And because of that he didn't put up a fight. Idk I could be wrong:
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T was could, I just wanted a brief sum up