I'm probably going to get s*** for this, but I think Chiarelli has been pretty average aside from one good year, and that year was 2006 (2006 draft, signing Chara and Savard). His draft since 2006 consists of Seguin (idiot proof), Hamilton, and possibly Pastrnak, with some maybes in Colborne, Caron and Griffith. As for trades, his record is mixed:
Good:
Kessel trade
Rask trade
Boychuk for Hendricks
Horton trade
Bad:
Seguin trade
Boychuk trade
Versteeg trade
Kaberle trade (Leafs acted like idiots with their picks)
Sobotka trade
All that's left is his free agents, where I don't know his history as well beyond Chara and Savard. Overall, he seems like an okay GM who got really lucky with inheriting Bergeron and Thomas.