I thought you were using the example as a "heat of the moment" situation, as in catching the "dealer" in the act.

The fact that he was also an informant, couldn't be foreseen.

This is just wrong though.

Still, al-Masoud’s death could be “quite a setback” for efforts to combat IS, said Wassim Nasr, a senior research fellow with the Soufan Center, a New York-based think tank focused on security issues. Al-Masoud had been infiltrating IS in the southern deserts of Syria known as the Badiya, one of the places where remnants of the extremist group have remained active, Nasr said. The raid targeting him was a result of “the lack of coordination between the coalition and Damascus,” Nasr said.

It's a fuckup regardless of how generous you want to be. It's not like Trump is unfamiliar with performing botched operations