Revisiting the Maple Leafs Trade of Phil Kessel to the Penguins – Hockey Writers – NHL Trade Analysis

Phil Kessel was traded from the Boston Bruins to the Toronto Maple Leafs on September 18, 2009, for a first round pick and a second round draft pick. At the time, Kessel was a young and talented player who had shown promise. However, he also had some ups and downs, and the Bruins wanted to move him in free agency and acquire other draft picks.

The Kessel Trade was controversial

The trade was controversial. Some Maple Leafs fans weren’t happy about giving up so many picks on Kessel. However, he became a key player for the team, scoring 30 or more goals in his first three seasons with the team. He also earned two All-Star Game appearances in six seasons in Toronto.

The truth is, even though the trade was criticized by fans on both sides, it worked out well for both teams. The Bruins used their draft picks to select talented players, and the Maple Leafs landed a talented player that helped them compete for a playoff spot.

Kessel Was The Penguins Wanted Asset

Kessel gave the Maple Leafs six solid seasons; scored more than 30 goals four times and 25 once.

Related: Phil Kessel – Biography of an NHL Star

However, on July 1, 2015, Kessel’s time with the Maple Leafs ended when he was traded to the Pittsburgh Penguins. Going with him to Pittsburgh were Tim Erixon, Tyler Biggs, and a conditional second round pick in the 2016 Draft (which became Kasper Bjorkqvist). Returning to the Maple Leafs were Nick Spaling, Scott Harrington, Kasperi Kapanen, a first round pick (which became Sam Steel), and a third round pick in the 2016 Draft (which became JD Greenway).

The Maple Leafs traded Steel to the Anaheim Ducks in June 2016 for a second round pick (which turned out to be Maxime Comtois) for Frederik Andersen. Greenway never played in the NHL.

While Kessel may not have been a fan favorite, many still believed the team didn’t get enough return for their leading scorer. Maybe they had a point. Kessel went on to help the Penguins win two Stanley Cups, while the Maple Leafs struggled for consistent scoring in the seasons following the trade.

Which Led to Kessel’s Trade in Maple Leafs

There are several factors that contributed to Kessel’s trade. First, the team failed to make the playoffs in his last three seasons in Toronto. He also saw a slight dip in his production, scoring fewer goals and points last season.

In 2013-14, he scored 37 goals and 43 assists (for 80 points) in 82 games. Although the following season was still good, his scoring production dropped by almost a point. In 2014-15, he scored 25 goals and 36 assists (for 61 points) in the same 82 games.

Related: Phil Kessel Went to Toronto Maple Leafs Trade and Revisited a Decade Later

Second, Kessel’s salary became a burden. He was one of the top players on the team, and it was clear that the Maple Leafs were not Stanley Cup contenders – even without Kessel. It was time to rebuild.

Third, Kessel (rightly or wrongly) had developed a reputation as a difficult player to work with. Conflicts with coaches and teammates were reported. If the Maple Leafs were going to change their culture and leadership, it seemed clear that they had to “out with the old and in with the new,” meaning it was time for Kessel to move on.

Fifth, the Penguins wanted Kessel. They were looking for a goal scorer to play alongside one of the best players in the world – Sidney Crosby – and he seemed like the perfect fit. He was. While the Penguins looked over the fence on the Maple Leafs’ roster, Kessel was a pure scorer who could consistently put up around 30 goals a season.

Who Won the Kessel Trade?

It’s hard to say which team won the 2015 Kessel trade. Much depends on how the trade is evaluated. However, both parties benefited.

Related: Greatest Lines of the Pittsburgh Penguins

The immediate impact was in favor of the Penguins. Kessel arrived and did exactly what his new organization had hoped and expected. In 2015-16, his first season there, he posted 26 goals and 33 assists (for 59 points), and the Penguins won the cup. In 2016-17, he scored 23 goals and 47 assists (for 70 points) en route to a second straight championship. Kessel continued to produce for the Penguins over the next few seasons.

The Maple Leafs received a package of players and draft picks in the trade, which they used to rebuild their team, including a highly regarded prospect named Kasperi Kapanen.

Kapanen played parts of five seasons with the Maple Leafs, culminating in a 20-goal season in 2018-19. He moved on, but the first-round pick was used on Timothy Liljegren, who was the team’s strong young defenseman before they traded him to the San Jose Sharks on Oct. 2024.

Both Teams Got Something They Needed

Both teams benefited from the trade, making it difficult to declare a clear winner. However, in Kessel, the Penguins got a high-scoring winger who helped them win two Stanley Cups, and the Maple Leafs got a few pieces that helped them rebuild their team.

Most notably, they inadvertently took Andersen, forward Kapanen, and defender Liljegren.