The trades are starting to pick up as the Leafs ship out another pending UFA in Daniel Winnik to the Pittsburgh Penguins for Zach Sill, a 2nd round pick in 2016, and a 4th round pick in 2015 with the Leafs retaining 50% of Winnik's salary for the rest of the season ($1.3M caphit = $650k retention caphit). (Edited per new information). Who is Zack Sill you might ask? I know I did. Turns out, he's not very good. Likely, this was important from a contract-swapping perspective or the Leafs needing bodies to play in the AHL after they clear the decks at the NHL level and bring up real prospects to finish out the year. Or maybe he stays up to ensure the Leafs get as close to third last place (godspeed but nobody is catching Edmonton or Buffalo) as possible. What he certainly is not is a good hockey player. Yikes.
It's no secret that Winnik was on the way out before the deadline (exhibits A B C) which turns into a nice bit of business for the Leafs after he was signed for free on July 28, 2014. Winnik recognized the value of playing under the media spotlight in Toronto and it's paid off as he's bringing back two draft picks. Of course, with Dave Morrison at the helm there is a question about just how valuable those picks will turn out to be but based on Steve Burtch's work, we shouldn't expect too much out of them.