I have a theory as to how Winn went from being the Vedek of an order 'barely heard' in the season 1 finale to being voted as Kai a year later.
Jaro is the reason she got elected as Kai.
Specifically, she used her knowledge of him while they were planning on getting power together to leapfrog her status as someone working for the greater good of Bajor. Note how very quickly she turned on him when Kira presented the evidence in "THE SIEGE".
By the time of "THE COLLABORATOR", she was so raised up in status from before that her ONLY threat to being elected Kai was Bareil, and we saw what happened there in that episode.
As for Jaro's fate, he was almost certainly put in prison. And quite likely killed there by another inmate for almost getting the Cardassians back or even Winn ordered him killed to make sure she couldn't be connected to him.