It's difficult to develop that 'hate-to-lose' culture when ownership/management keeps moving the guys who truly hate to lose out of the organization.
O'Reilly hated to lose, put that feeling into words, and was traded.
Eichel and Reinhart were sick of losing and didn't want to go through another rebuild. Adams claimed that they didn't want to be here, traded them and then proceeded with his idiotic and doomed rebuild.
It's difficult to build that hate-to-lose culture when you label those players who voice dissatisfaction with losing as dissenters to the cause, and then move them out of the organization.