They've been one of the smartest organizations for over a year now, ever since they hired Shanahan. He hired analytics prodigy Kyle Dubas as AGM and the franchise went from having no advanced stats presence to the largest analytical department in the league. Shanahan also hired Mark Hunter, who had a ridiculously successful track record drafting and developing stars with the London Knights. As a Leafs fan, it feels very much like the first couple of years under Theo. Still a long way to go, but it's just a huge change for the organization to be continually making smart moves in a proper rebuilding effort. The farm system has gone from bottom 5 to top 10 in two drafts as they continue to target as many skilled forwards as possible (much as the Cubs target the best bat available). They also use free agency like the Cubs did, picking up undervalued veterans on short deals with the intention of flipping them at the deadline for assets. They did it with Santorelli and Winnik last year, Parenteau is an obvious candidate this season. I am extremely underwhelmed with the Kessel return, but I am willing to cut them some slack since essentially every other transaction has been great. I think Kessel's salary and NMC really left the team without many viable suitors. Why they absolutely had to move him, I'm not sure. Obviously either Babcock or Shanahan absolutely wanted him gone. Very disappointing. On the other hand, having an elite sniper in his prime on a rebuilding team doesn't make much sense either.