I give kudos to DS for building a 'team'.
Bill Belichick has a great line "We're building a team, not collecting talent."
At this point, I think that we can all agree Sweeney has done a great job building a team that can compete for the Stanley Cup. He has made a mix of good and bad moves, but the key has been limiting the mistakes so they don't come back to hurt him.
Now, I don't want to turn negative, but there are plenty of Sweeney's moves I haven't liked. Chief amongst them was the decision to go for a re-tool versus a re-build. Hell, I wanted Cassidy fired from Providence years ago when we weren't developing any young players. When decisions work out, you look like a genius, and when they don't, well, that's when the pink slips come out. Sweeney has been more right than wrong. We love to be armchair GMs here, but there's a reason he's a GM in the NHL, and I'm sitting here typing this out on a Friday night.
To me, the most important quality for a GM is to be able to "self-scout". Just after that, is asset management. We point to the 2015 draft or the Beleskey signing (and some even mention the Backes signing) as moves we don't like. The ones I think about are not getting value for Eriksson at the 2016 trade deadline, and trading away significant draft capital for Rinaldo, Liles, and Stempniak. However, that was Sweeney's first year at the helm, and like our young players, he has grown and developed.
We're in a good spot now, but I think Sweeney's real test is yet to come. We should have a Cup contender for at least the next two years. Can Sweeney sign the young guys and negotiate the expansion draft so that Cup contender period is for an indefinite amount of time? Chiarelli made mistakes and closed the window. Has Sweeney learned from that? We're going to see over the next few years. I, for one, am hopeful for the future.