Chiarelli's drafting and developing is the most worrying for me.
Since 2006, the Bruins record for drafting and developing is pretty horrendous.
Lets say the cut off is 150 games for argument sake. Ie drafted dude helps team for 1.5 seasons or more.
2006:
Kessel
Lucic
Marchand
2007:
None
2008:
Colborne (all for Flames)
2009:
Jordan Caron
2010:
Tyler Seguin
2011:
Dougie Hamilton
Under his guidance, the Bruins have drafted and developed 7 players who have played >150 games for that team. The latter 2, came via high picks due to the Kessel trade. Colborne didn't really don a Bruins jersey so he's basically a non-factor too.
It's a pretty barren list in terms of drafting and developing.
I'm going to assume Chiarelli had basically no say in the 06 draft cause of when he was hired, but if he did that draft was flat out amazing. His first 3 drafts that I assume he had oversight of look bad, the 10,11, & 12 drafts look pretty average where I think they will get 2 NHLers out of each and 13 & 14 are too soon to tell. Boston has prided itself more on being well rounded and having good role players through out the line-up and building a cohesive team. Pittsburgh is more of here are our stars, let's just plug the holes around them the best we can with the money we have left, the quality of their role players on the 3rd & 4th line and 3rd pairing d-men have generally been lower and it's easier to sneak into their line-up then it is with Boston so games played shouldn't be the only benchmark seperating the two.
From 2010- Ryan Spooner is a pretty good prospect he's just taking the long road to get there like Lander, but I think he will have a good career infront of him.
From 2011- Alexander Khokhlachev is very talented, he seemed pretty raw when I seen him so he's the kind that will take a bit longer, but he fits the mold of players I see Detroit pick up, then fast forward 5 years later and they are amazing all of a sudden.
- Anthony Camara is probably safe to write off considering how bad his offensive numbers are, but I do remember him being strong defensively kind of the equivalent of Ewanyk, but he does enough little things right that sometimes coaches take a shine to them and they can play a fair number of games.
2012- Malcolm Subban is a top shelf goalie prospect and the number of even really good goalies prospects that play many games at age 21 is extremely rare. All indications are this was a very good pick up to this point.
-Seth Griffith is a great pick for the 5th round watched him a ton as a London Knight the kid is a gamer, he could have a long career infront of him based around his great work ethic and pretty decent hands.
Pittsburgh's draft record just seems like they are really good at drafting and developing defensemen, almost exclusively specializing in it, the only forwards they drafted of note in Shero's time was Jordan Staal at 2nd overall in 06 (which he probably had no say in cause of when he was hired) and Beau Bennett at 20th overall in 2010 who looks like he might be a bust. They have one goalie drafted of note in Tristan Jarry in 2013 who we are all familiar with.
So from what I see in their histories is Shero has the formula for drafting and developing young d-men and Chiarelli has the ability to trade for quality d-men who were undervalued by their current clubs. Being that Nicholson has already appointed Bob Green as the director of player personnel and will be overseeing all the scouts, I don't see Chiarelli's duties if hired as overlapping on what Green is doing. He'd probably be more focused on the trading aspects and making decisions on potential UFA acquisitions, essentially just another person in the room at the board table helping make the decisions. It all depends on how you compartmentalize things, but I can only assume he would be used to do what he is good at and kept away from things that are not his area of expertise.