After another disappointing season for the Toronto Maple Leafs and Pittsburgh Penguins, with both being eliminated in the qualifying round, a big trade in the offseason was bound to occur. The Penguins wanted to get young and wingers for Crosby and Malkin while the Leafs wanted cap space. Unexpectedly, on the morning of August 25, the Penguins brought back a familiar face, Kasperi Kapanen.
 To TorontoÂ
2020 first-round draft pick (15th overall)
Filip Hallander
Evan Rodrigues
David WarsofskyÂ
To Pittsburgh
Kasperi Kapanen
Pontus Aberg (rights)
Jesper Lindgren
Kasperi Kapanen was initially drafted by the Pittsburgh Penguins with the 22nd pick in the first round of the 2014 NHL Draft, but was then flipped to the Maple Leafs in a blockbuster trade that sent Phil Kessel to the Penguins. In the 202 games Kapanen played for the Leafs, he recorded 90 points (41 goals and 49 assists). The Penguins also acquired the rights to Pontus Aberg who is currently in the KHL (Russia) and Jesper Lindgren, a former fouth round pick and is currently playing in the AHL.
The Leafs got a huge haul for Kasperi Kapanen which included a first-round pick (15th overall) which the Leafs can use to draft a great prospect in the deep 2020 draft. Another big piece in the trade was Fillip Hallander, a promising young prospect taken in the second round of the 2018 NHL Draft. Evan Rodrigues is an add-on to the trade, acquired for depth with David Warsofksy who is just there for a roster spot.
Winner: Maple Leafs
Even though the Penguins are desperately trying to win another Stanley Cup before Crosby and Malkin are past their primes, they gave up too much for Kapanen who will most likely be a second or third-line winger for the Penguins. Meanwhile, the Maple Leafs will free up $3.2 million in cap space which they desperately needed along with getting yet another great prospect with the 15th pick and get a solid defensive prospect in Hallander.