Jim said the Blackstaff chooses the wizard. Now I actually interpreted it meaning the Blackstaff itself chose the wizard but I think someone showed that Jim meant the Blackstaff wizard chose the next Blackstaff. Well the position is very very dangerous. Eb has got to know that there is a good chance someone will take him down before he can hand it down to someone else. So my guess is he has in advance chosen who will take is place at the time of his death. Who would you see him picking?
I could see him picking Harry, believing Harry is the right guy for the job, but I'm also thinking Luccio might be his pick (perhaps so Harry wouldn't have to live with the nightmares of what he would have to do).
That is exactly the kind of word lawyering I would expect from a sneaky little author like Jim.
For me, candidates would include Harry, Ramirez, Luccio, Chandler, and Listens-to-Wind.
1. Harry is the most likely choice. Eb clearly has faith in him, and believes he can handle the burden of being The Warden. But I think circumstances have changed too much; with his Wardening and Knighting he has to do full time, adding the office of Blackstaff might be too much for Harry to handle, and I'd expect Eb to think similarly.
2. Luccio is doable, but I think she'd be too rigidly in support of the laws. Not to Morgan levels of insanity, but not flexible enough. Plus, after the body switch, she's lost her full potential, and has proven susceptible to mind alteration.
3. Listens-to-Wind is more likely, I think, specifically because Eb respects his ability to rein in his anger and outrage, and act dispassionately, according to his conversation in Turn Coat. Seems like a good candidate for someone with power over life and death. Plus, imagine what access to black magic could do for a Healer.
4. Ramirez is a bit of a stretch. He's proven brave and loyal, and can think outside the box. But Ebenezer doesn't know him well enough yet for him to be seriously considered, I think.
5. Chandler is my longshot. Capable, dependable, and loyal in enough quantities that he's trusted by everyone on the Council, even the top brass. Harry notes he's been seen in positions that would require great trust too often for it to be a fluke.
Really, it depends on what you think the role of the Blackstaff is. I see it as a check against the Council's arrogance and politicking, when action is being deliberately halted or slowed by bureaucracy and the rules and Laws are twisted against their purpose of protection. Eb would want it passed to someone who is as far away from that nonsense as possible.