Ashe harbors a significant grudge against Cassidy primarily because he chose to join Blackwatch, a covert division of Overwatch, following the apprehension of their shared gang, a decision she interpreted as a profound offense or betrayal.
Their tumultuous relationship stems from events predating the current Overwatch timeline, rooted in their past as members of the notorious Deadlock Gang.
The Incident That Sparked the Grudge
Years ago, the Deadlock Gang, which both Ashe and Cassidy (then known as Jesse McCree) were part of, was busted during a sting operation conducted by Overwatch. This pivotal event led to a fork in Cassidy's path. Faced with the stark choice of serving prison time or joining Blackwatch, Overwatch's shadowy black-ops division, Cassidy opted for the latter.
Ashe's Perception of the Choice
Ashe's animosity developed from her interpretation of Cassidy's decision. It is suggested that she might have been unaware of the limited options Cassidy was presented with—either joining Blackwatch or facing a long prison sentence. Regardless of his constrained circumstances, Ashe viewed his choice to align himself with Overwatch as a direct betrayal of their gang and the loyalty they shared. This perception of him abandoning their shared life and principles to work with the organization that busted them fueled her long-standing resentment.
Lingering Resentment
Ever since that incident, Ashe has maintained a strong personal vendetta against Cassidy. Her disdain is a recurring theme in their interactions, reflecting the deep-seated anger and sense of betrayal she feels, making their encounters fraught with tension and animosity.