The Cubs are known to have interest in trading for the Rays’ Chris Archer, so Cole, should he be available to them, would make sense as a similar target.
As for the Pirates’ end ... man. I’m usually not too attached to guys or upset by seeing them leave, but seeing Cole with the Cubs would sting big time. Avoiding a divisional trade may be a consideration if the Pirates choose more of a reloading route as opposed to a scorched-earth rebuild, but, if the Cubs end up with the best offer, that’s probably a prudent deal to make. It’s worth noting, though, the Cubs have traded a lot away from their previously fertile farm system in recent years. They don’t have the obvious guys that would start a deal, like, say, the Yankees, anymore.
I just ... I don’t know. The Cubs???