The organization landed 2014 first-round pick Kasperi Kapanen, 22-year-old defender Scott Harrington, 26-year-old depth forward Nick Spaling and first- and third-round selections in the trade.
It's a substantive strike at reshaping the roster and precisely the reason why Toronto was right, at this stage in the game, to explore trading the player who led them in scoring in each of the past six seasons.
Kessel, who has rung up more points than all but five NHL players since 2011, always stood to offer the Leafs more value as a trade chip than a roster player on a rebuilding squad in the years ahead.
His age, hefty contract (seven years remaining at an annual cap hit of $8 million) and questionable fit didn't line up with Toronto's timetable on the long road back to contention. The assets they landed have the potential to help in that regard.
Kapanen fits in a prospect pipeline that continues to focus on high-end skill; a potential complement to a future forward contingent that includes fellow first-round picks Mitch Marner and William Nylander. He scored 11 goals as an 18-year-old in the Finnish Elite League last season and, like Nylander, is the son of a former NHL player (Sami Kapanen).
Harrington is a familiar face to Mark Hunter, Toronto's director of player personnel. He played four seasons with the London Knights before landing with Pittsburgh in the second round of the 2011 draft. He joins a young stable of Leaf hopefuls on the back-end that also includes Martin Marincin, Viktor Loov, Tom Nilsson, Rinat Valiev and Stuart Percy.
Morgan Rielly and Jake Gardiner are, of course, the young anchors of Toronto's present and future on defence.
The Leafs also added Spaling for immediate help up front; he has one year left before free agency.
In addition to Kapanen and Harrington, the draft picks represent the most potential value down the road. Toronto essentially landed two firsts (Kapanen and the future lottery-protected pick), a second (Harrington), and a third for Kessel. The Leafs also sent 2011 first-rounder Tyler Biggs, a future second-round pick and recent acquisition Tim Erixon to the Penguins in the deal. Toronto will also be absorbing $1.2 million of Kessel's contract for the next seven years.
It's anyone's guess whether the assets Toronto landed in the massive Kessel deal will work out, but the organization, at the very least, acquired potential puzzle pieces.