[Jefferson had figuratively "let go" of his family himself on more than one occasion. He's not going to be casting judgement on Rumple's parenting skills any time soon.]

I've traveled to Oz and am quite familiar with the Wicked Witch's reputation. I even stole from her once, a crystal ball right out of her vault, but she has no idea who I am. [as all good thieves should be able to brag. Infamy is for amateurs.

As for the switch to private video, he'd been getting hints from others about what's been happening here, but the details of the problem leave Jefferson with conflicting emotions about it. How torturous for Regina to be at the mercy of someone else. Regardless of her supposed "change of heart", Jefferson still holds a justifiable grudge against her. On the other hand, he held no enmity against Rumplestiltskin (despite the Dark One's actions in the Enchanted Forest), and he would rather not see that sort of power in the hands of anyone but Rumple's own.

It's the sort of situation where it really would be safer for Jefferson not to get involved.]

Could she do it? Would she be able to open a portal? [This causes Jefferson a very different sort of moral dilemma.]