Eh there were a few targets that I felt a bit of an asshole killing. "Zip Master" in Hitman 2 (As in the sequel to Hitman Codename 47, NOT the new Hitman 2) was some cult leader, IDK exactly how much evil he directly did, but I just felt a little bad killing some old dude while he's unconscious on an operating table undergoing a heart transplant. Dunno why but it just felt a little unfair, would have rather gone after him AFTER the procedure once he was on his feet, would have been a good opportunity for more character development since not much is really said about him. (There's paintings of him in other cult areas so he was influential.) At least Erich Soders in Hitman 2016 was plenty damn evil and I enjoyed both destroying his transplant heart, and going out of my way to murder him on the operating table to make him dead twice-over.
Sidjan and his bro were two hacker-dudes. Same type of thing, just felt a bit dick-ish considering we had to kill both him and his twin brother. Was a fun set of levels though.
Clarence in Blood Money also was kinda depressing. Imagine owning an amusement park, having a accident kill tons of people, get sued for everything, manage to win the lawsuit but lose all your money in court costs, lose your reputation, your wife, then having to rent your property out to an abusive crack cocaine ring to stave off bankruptcy who takes advantage of you. Then one of the fathers who had their child die in the accident hires a hitman to kill you.
Aside from a select few others, (World of Tomorrow, Silvio Caruso, some mentally ill savant who was abused his whole life and working on some sort of bio-weapon and the company working on it has both him, and the person who warned everyone about it killed.) the rest pretty much deserved it. Especially the guys in Traditions Of The Trade who were terrorist bombers.