Ranking the 5 Biggest Losers From the 2025 NHL Trade Deadline

1. Edmonton Oilers

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Stan Bowman is entirely out of touch. The Edmonton Oilers GM continues to make bad decision after bad decision, undoing all of the good Ken Holland brought to this franchise.

The Oilers were rumored to be in the market for a versatile defender and a scoring winger. Coincidentally, they had both players on their roster during last year's run to the Stanley Cup Final. But instead of matching the offer sheets on Philip Broberg and Dylan Holloway, the Oilers decided to fill those holes at a more detrimental cost. 

No offense to Jake Walman, but he's getting $1 million less than Broberg and doesn't come close to matching his production. Likewise, the Oilers decided to ink Jeff Skinner to a more lucrative contract and he has 26 fewer points than Holloway. In summation, at roughly the same cost, Edmonton has two worse players in Walman and Skinner. And they gave up a first-round draft pick to accommodate those transactions.

The Oilers need to rid themselves of Bowman before he does more damage. 

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EDM Oilers To Win Outright +750

4. New Jersey Devils

5 Teams That Made the Most Impactful Deadline Day Moves

The New Jersey Devils were in a precarious position. Days ago, they lost Jack Hughes to a season-ending shoulder injury. Rather than using future capital to replenish his loss, the Devils made only a couple of minor deals, signaling the beginning of the end. 

Cody Glass was the most notable acquisition, but he won't come close to replacing Hughes' production. Likewise, Daniel Sprong and Marc McLaughlin offer no value.

The Devils should have set their sights on a true rental. A player like Brad Marchand, Brock Boeser, or even Scott Laughton to enhance their competitiveness into the playoffs. By the time Hughes is back next year, Jacob Markstrom will be almost 36 years old and on the decline. As will the Devils' Stanley Cup odds.

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NJ Devils To Win Outright +3000

3. Chicago Blackhawks

Impact of Trades on Cup Odds: Before and After Analysis

The Chicago Blackhawks made a significant move a few days before the deadline. They traded Seth Jones to the Florida Panthers for Spencer Knight and a first-round draft pick in 2026. Unfortunately, there were no other substantive moves, dooming the Hawks to ongoing misery. 

Chicago's top line is the only lifeline keeping the Hawks afloat. Otherwise, they have a mishmash of aging players and tertiary contributors who would have been much more valuable to playoff-contending teams. As we've seen, there's little those players offer to the current iteration of the Blackhawks. 

No rebuild is easy, but it becomes especially difficult to build a contender when you're unwilling to acquire the necessary pieces. In that regard, Chicago continues to fail. At this rate, it won't be long until Connor Bedard demands his way out.

Bet365 NHL FUTURES ODDS

CHI Blackhawks To Win Outright +450000

2. Pittsburgh Penguins

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There may be a few glass-half-full people out there who are willing to commend Kyle Dubas on a job well done, but we're not one of them. The Pittsburgh Penguins have imploded this season, failing to capitalize on the twilight years of their aging core. Rather than selling off every player they could, the Pens elected to move bits and pieces for early-to-mid-round draft picks that do nothing to help Pittsburgh over the next few years. 

Rickard Rakell and Bryan Rust should have been on the move at the deadline. Both players earn more than $5 million and are over 30 years old. Neither skater has been the type of player the Penguins need them to be. Both have significantly underachieved, and their value only diminishes moving forward.

Ridding themselves of a few bad contracts could have been the difference for the Pens. They could have used those savings to make a big splash this offseason. Now, Pittsburgh will be forced to run it back with the same disastrous roster next year, tarnishing the legacy of their once-proud dynasty.

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PIT Penguins To Win Outright +70000

1. Edmonton Oilers

Check Here for the Most Up-to-date NHL Odds.

Stan Bowman is entirely out of touch. The Edmonton Oilers GM continues to make bad decision after bad decision, undoing all of the good Ken Holland brought to this franchise.

The Oilers were rumored to be in the market for a versatile defender and a scoring winger. Coincidentally, they had both players on their roster during last year's run to the Stanley Cup Final. But instead of matching the offer sheets on Philip Broberg and Dylan Holloway, the Oilers decided to fill those holes at a more detrimental cost. 

No offense to Jake Walman, but he's getting $1 million less than Broberg and doesn't come close to matching his production. Likewise, the Oilers decided to ink Jeff Skinner to a more lucrative contract and he has 26 fewer points than Holloway. In summation, at roughly the same cost, Edmonton has two worse players in Walman and Skinner. And they gave up a first-round draft pick to accommodate those transactions.

The Oilers need to rid themselves of Bowman before he does more damage. 

Bet365 NHL FUTURES ODDS

EDM Oilers To Win Outright +750