I have 2 in mind.
1. Nick Franco. Cheater, womanizer, big-time Playboy. Not caring about whose heart he stepped on to get there.
2. Edna from Swan Song. The way that she treated Tommy Brown was pure despicable.
I don't know if he really had it coming, but I wasn't upset when Jesse Jerome was killed. I'm not excusing what Santini was running from, but Jerome seemed like such a despicable person who only cared about the almighty dollar.
This is just my opinion but I feel like most blackmailers have it coming. Not the point the finger at anybody specific in the series but blackmailing is definitely a high motive for killing.
Gene Stafford in "Exercise In Fataliy" is near the top of "You asked for it" because the man has no sense of cautionary tact to realize that openly threatening a guy who he *knows* could at the very least rough him up physically is just......DUMB.
Lessing certainly deserved it and it was an accident. That was why the script then had to give us Vivica committing a second pre-meditated murder so that the audience at the end wouldn't feel sorry for her when she gets caught.
I would say Tony Galper in "Columbo Likes the Nightlife."
He wasn't just a bad guy, but his death was an accident while Vanessa was defending herself.
In the same episode, Linwood was also a despicable victim, but that was a cold-blooded murder, which makes it harder for me to say he "deserved" it.
I was seriously considering those two also quid.
Yeah, Edna got what she deserved!
I don't know about deserving it, but Karl Lessing really "asked for it."
Not only did he PRETEND he was willing to negotiate with Viveca, he also pretended that he wanted HER back.
Another vote for this bum.
Everybody hated the creep. He treated his business partner and staff like dirt.
And, worst of all...
He was willing to ignore Santini's secret career in the Nazi SS if he paid him off; and....Jerome was Jewish.
Santini deserved a medal....before we gassed him.