Church has never been so determined to torture Wild Dog. Can he live up to the sufferings? Will he jeopardize Oliver's leadership as the mayor and the "Green Arrow" to save himself? That doesn't sound quite like him but we never know.
It didn't help that Oliver went out into the open and expose himself to the enemy by disclosing his real identity. He used to be very overprotective when it comes to who he really is even to the "Team Arrow" members. It just declined over time, according to Cinema Blend.
Fighters Diggle and Sara existence in the show deemed important for the season. Felicity has been his savior despite not knowing that he's the Emerald Archer they can look up to in "Team Arrow".
Roy was well guided and was away from harm by not allowing him to challenge the field before he becomes capable enough to fight. Thea has also advanced in her craft after experiencing Malcolm Merlyn's League of Assassins boot camp for the "Team Arrow."
Perhaps Oliver realized that he should stop limiting great fighters to prevent them from dying. They will go out of their way anyway. Laurel's disguising herself with Sarah's signature costume and pretending to be a boxer are some classic strategies to prevent Oliver from isolating her and become a stagnant "Team Arrow" member.
She died despite Oliver's over protectiveness. The new fighters are more like her. So, what should Oliver do now? He cannot spend all his time limiting them from going out of the field. They should enter at their own risk and discretion with little supervision. That's how responsible "Team Arrow" member should be.
On the other hand, Wild Dog's capture can be the breaking point to force "Team Arrow" to enhance their tactics and make some significant changes. If you are curious on how they would go about that exactly, watch "Arrow" at CW every Wednesday at 8 p.m., as listed in the TV Guide.
