The trade deadline and trades overall benefit the team that acquires the best player in the deal. At least that’s the common thought behind most deals in what is known as a buyer’s market. Usually, the teams that are labeled sellers have to trade star players for pennies on the dollar.
Related: Top 10 NHL Trade Rentals Who Didn’t Win the Stanley Cup
That said, some trades allow the selling team to bottom out and end up in a lottery position for the NHL Entry Draft. While teams don’t tank, especially the players and coaches, front offices can move on from a player, and by doing so, they set themselves up for an effective rebuild and long-term success. Some instances of this helped set up perennial Cup contenders as they were finally able to draft elite talent.
Blackhawks Trade Patrick Kane (2023 Trade Deadline)
To understand the payoff of the Patrick Kane trade, it’s important to look back at the Alex DeBrincat trade, which happened in the 2022 offseason. The Chicago Blackhawks sent him to the Ottawa Senators in a deal that both gave them a big haul and set them up for a good lottery position. Looking back, it heavily benefitted the Blackhawks since DeBrincat was traded the following offseason for a much lower asking price as he went from the Senators to the Detroit Red Wings.
Then came the Kane trade at the 2023 Trade Deadline. By moving their top player and the face of the franchise, the Blackhawks made it clear they were chasing the top pick in the 2023 Draft. Kane, even in his 30s, was playing at a high level and early on in the season, he helped the Blackhawks win a few games they otherwise would have lost. Without him, they were in prime position for the number one overall pick. That pick was Connor Bedard, a generational talent who can transform a franchise.
The early years of general manager (GM) Kyle Davidson’s tenure were crucial for success. The moves he made put a lot of young players on the roster to build around. The 2022 draft class alone gave them Kevin Korchinski and Frank Nazar, a two-way defenseman and a center who will play pivotal roles on the roster. The Kane trade was the final masterstroke as it helped them land Bedard and put together a great young team that should compete for years to come.
Maple Leafs Trade Phil Kessel (2015 Offseason)
Following the 2013 first round defeat, the Toronto Maple Leafs became a team on the decline. It was clear they wouldn’t contend with the group they had. However, they were good enough to remain out of draft lottery position. That changed when the Maple Leafs traded Phil Kessel to the Pittsburgh Penguins in the 2015 offseason.
Kessel at the time was one of the best players on the Maple Leafs, scoring 20 goals and 25 assists or more in all six of his seasons with the team. He was good enough to allow the Maple Leafs to win enough games to remain out of lottery position. By trading him, they were one of the worst teams in the NHL in the 2015-16 season and it allowed them to draft Auston Matthews with the number one overall selection in the 2016 Draft.
Suddenly, the Maple Leafs had a young core that would compete for years to come. Mitch Marner and William Nylander were already in the pipeline and with Matthews making an immediate impact, they successfully rebuilt their roster. Throw in the John Tavares signing in the 2018 offseason and they had a core four to contend for a Cup (something that has yet to happen but with the group still together, it’s only a matter of time before it does, right?).
This trade also worked out for Kessel. He went to the Penguins just as they were hitting their stride. He won the Stanley Cup with them in 2016 and 2017 and in the 2022-23 season, helped the Vegas Golden Knights win it all. Leaving the Maple Leafs was what kickstarted Kessel’s career.
Oilers Trade Ales Hemsky (2014 Trade Deadline)
The Edmonton Oilers were in a decade of darkness where there seemed no end in sight. Then came the 2014 Trade Deadline. The Oilers would have to trade a face of the franchise but it was a price worth paying when they moved Ales Hemsky to the Senators.
This ended up becoming one of the more one-sided trades in recent memory, not because of what the Oilers received in the deal but what it did for them in the long run. The Senators got Hemsky to make a push for a playoff spot and they came up five points short. Hemsky left in free agency, signing with the Dallas Stars, and the Senators were left empty-handed from the trade. The Oilers started the next season slated to be one of the worst teams in the NHL and that’s what happened. They went 24-44-14 and fell to the bottom of the standings to win the lottery and ended up with the top pick in the 2015 Draft.
Who was that pick? Connor McDavid! One of the greatest players of all time, he turned the franchise from a perennial bottom-feeder into a title contender every season. The Oilers were one win away from winning the Stanley Cup last season and it’s noticeable McDavid was the reason why. He has carried the team throughout his tenure and led them in the Final to force a Game 7 despite the team trailing 3-0 in the series. If this team ends up winning the Cup, it will be because of their star player who they got in part by trading Hemsky in 2014.
Lightning Trade Vaclav Prospal (2008 Trade Deadline)
The Tampa Bay Lightning rarely sell at the trade deadline. One of the times they did end up working out. They traded Vaclav Prospal in 2008 to the Philadelphia Flyers and it pulled the rug out on the season. The Lightning went 6-10-2 after trading one of their best players and ended up with the top pick in the 2008 Draft and selected Steven Stamkos. Interestingly, they re-signed Prospal in the 2008 offseason only to buy out his contract after the 2008-09 season.
After the Lightning drafted Stamkos, they remained in rebuild mode and a lottery team. In 2008-09, they were one of the worst teams in the NHL and with the second overall pick in the 2009 Draft, they added Victor Hedman to the roster. Suddenly, the Lightning had two core pieces to build around with an elite forward in Stamkos and a two-way defenseman in Hedman.
The Prospal trade seems like a minor one even though he was one of the best players in the league at the time. However, the trade put the Lightning on track to rebuild and put together a great team. The Stamkos selection had a direct correlation to that deal and he became a key part of turning the Lightning into a model franchise, one that would appear in the Final four times in a 10-year span and win the Cup in 2020 and 2021.
Other “Best Selling” Trades
There have been a few firesales in recent years and only time will tell if any of them will work out. The Senators had a teardown in the 2018-19 season when they traded Erik Karlsson, Matt Duchene, and Mark Stone to help them rebuild. By moving on from all their core players, they were able to draft a new core to build around but they still have yet to turn the team into contenders. The San Jose Sharks recently did the same thing, trading Karlsson in the 2023 offseason and then moving Tomas Hertl at the 2024 Trade Deadline. Both teams have yet to see their firesales pay off.
It’s easy to look at every team that trades away talent at the deadline as the loser of the deal. They are suddenly forced to rebuild and hope it works out. These trades prove that sometimes, the best path to contention is to tear down the roster or at the very least, move on from one of the best players on the team.
Is there a trade that has set a rebuilding team up for long-term success? Let us know in the comment section below!
