It'd be a messy little blow-up, that's for sure. Fucking with technobaby is a sure-fire way to (eventually) kill yourself, but...well...hate makes folks do crazy stuff, sometimes. And no one of Jackpointer caliber is ever going to admit, maybe even to themselves, that there's a job they can't pull off. It takes confidence to run the shadows, and to people who are used to dodging megacorporations and federal governments, there's the distinct possibility that "just a few shadowrunners" might not (on the surface) seem like as much of a threat.
So to us? Sure, Clockwork would have to be friggin' insane to try it. We can all see the Jackpointers likely to come crashing down onto him if he gives it a go, we can see how dangerous a group of people they are, we can see how nasty the rest of his life is going to be if he hurts technobaby. But to Clockwork? He's done this sort of thing before. He's pissed off families before. He's snatched technos before. If he goes into it cold and mean and plays it like he has in the past (and, in his head, he will)...he can pull it off.
Obsession and hatred make smart people do stupid, dangerous, things. If you're already used to doing dangerous things...yeah. I could see him making a play. Eventually.