2015
The time leading up to the 2015 trade deadline was a fairly active one for the Leafs. Perhaps in an effort to kickstart a rebuild, they acquired 6 draft picks in the month prior. One of these picks was a first round selection in that year’s draft, in addition to Brendan Leipsic and Olli Jokinen. Going the other way was Mike Santorelli and Cody Franson.
The first rounder turned out to be the highlight here, as it was traded down twice in order to draft Travis Dermott 34th overall.
Fans may also remember this deadline as the one the Leafs pulled off the impossible. They were finally able to unload the David Clarkson contract to Columbus. In return for the 7 years, $5.25 million deal, the Leafs received Nathan Horton. The LTIR ridden winger would allow for some cap relief, as his contract was taken off the cap due to injury.
Also around this time of year, teams are looking to not only dump players and contracts but to add veteran presences for the playoffs. In this event, it was the Pittsburgh Penguins offering Zach Sill, as well as 4th and 2nd round picks. The latter would turn into Carl Grundström in 2016.
In return, the bottomfeeder Leafs sent Daniel Winnik.
A few even more miniscule deals were sprinkled in. Overall, a decent stretch of trades that would offer some relief, and add some organizational depth.