Since Stan Bowman was hired on July 24, 2024, he has been responsible for signing 50 contracts for the Edmonton Oilers organization. To narrow them down for grading purposes, only contracts that have had the greatest impact or are soon to have an impact on the NHL roster will be graded; most entry-level and depth deals will be omitted.

The grade will be based on term, cap hit, clauses, and what the team expected or expects of the player.

Date: Sept. 3, 2024

Terms: eight years, $112 million ($14 million cap hit)

The first deal that Bowman ever signed with the Oilers has also been his best. Signing one of the best players in the world to a contract that was not only max-term but also a very reasonable cap hit that will only become more and more of a steal as the cap continues to rise dramatically was excellent business. Comparing it to the contracts of Leo Carlsson or Kirill Kaprizov already makes it look like a bargain, and it’s only a year old. It was also the first step in ensuring that Connor McDavid signed his own extension, which we will get to in a bit. This deal expires in 2033, when Draisaitl will be almost 38, virtually ensuring that he will be an Oiler for life.

Jan. 17, 2025

Terms: one-year, $1.755 million cap hit

After Klingberg signed a one-year deal with Toronto in July 2023, he only played 14 games for the Maple Leafs before missing the rest of the season and then undergoing hip surgery, which would cause him to go unsigned and miss the beginning of the 2024-25 season as well. While that gave many general managers pause when it came to signing Klingberg, Bowman’s gamble paid off fairly well, as the Swede became a legitimate part of the 2025 Stanley Cup Finalist team’s blueline, featuring in 19 playoff games and picking up four points.

April 19, 2025

Terms: two years, $2.6 million ($1.3 million cap hit)

Bowman re-signed Emberson to an inexpensive deal after his first season in Edmonton. Emberson’s dependability and reliable penalty killing are worth the low cap hit all day long, especially as a right-handed blueliner.

June 27, 2025

Terms: eight years, $30.8 million ($3.85 million cap hit)

Just days before he was set to become an unrestricted free agent, Bowman inked Frederic to what is undoubtedly the worst contract he has signed with the team. After being acquired from Boston, he played just one regular-season game before being an ineffective playoff regular. Rather than cutting losses and letting him walk, Bowman doubled down on the player and signed him to a maximum term, with a no-movement clause in the first four years. While it is pretty unlikely that he has as poor a season as the first year of the deal (four goals, seven points in 74 games) that saw him become a healthy scratch during the playoffs, this contract can only be considered a failure at this time.

June 30, 2025 | July 1, 2026

Terms: one-year, $1.3 million cap hit | one-year, $2.6 million cap hit

After being acquired via waivers, Kapanen was able to play up and down the lineup to end the 2024-25 season and became a reliable secondary contributor over the course of that playoff run. That stretch earned him an affordable extension, and his 2025-26 season, while often injured, proved even better. He put up four goals and six points in six playoff games last spring to earn him a doubled-up salary on another one-year deal. With solid secondary production and penalty killing skills, both deals look like wins.

June 30, 2025

Terms: four years, $42 million ($10.5 million cap hit)

Bouchard exploded for 21 goals and 95 points, and another seven during the playoff series against Anaheim in the first season of this bridge contract, already making it look like a slam-dunk win, even at a shorter term. Compare it to the likes of Cale Makar or Zeev Buium’s new contracts, and even though it is not max length, it is still outstanding value. The length is the only thing keeping it from being a full grade.

July 1, 2025

Terms: two years, $7.2 million ($3.6 million cap hit)

Added late in the day on July 1, Mangiapane was supposed to be another reliable middle-six winger with some scoring touch. That plan flamed out in a hurry as the forward was often healthy-scratched due to being a defensive liability and providing limited offence. He was waived in early March 2026, and after going unclaimed, Bowman needed to improve the draft pick they were sending to Chicago to a first-rounder for Dickinson and Dach in order to unload Mangiapane, further showing what a poor contract it was for Edmonton.

Sept. 23, 2025

Terms: three years, $8.85 million ($2.95 million cap hit)

Bowman and the team saw potential in Podkolzin after a solid first season in Edmonton that saw him produce 24 points in the regular season and another 10 in the playoffs. He improved the following season, racking up 37 points and becoming a regular linemate of Leon Draisaitl. By getting ahead of the game and extending the fan favourite at a relatively low price point early, this is looking like a savvy move.

Oct. 6, 2025

Terms: two years, $25 million ($12.5 million cap hit)

As easy as it would have been to consider any McDavid extension the best signing of the Bowman era, this deal, which kicks in this season, ranks behind Draisaitl’s due to its short term. It is still a full grade, as any contract for the best player in the world should be, but that is more due to McDavid taking a discount on his terms rather than Bowman’s negotiating skills.

Oct. 6, 2026

Terms: seven years, $49 million ($7 million cap hit)

This is another contract that begins in the 2026-27 season, but at this time, this one is looking questionable at best. Walman has shown a lot of positive results for the team when healthy, but is often a step behind when returning from injury, which is a common occurrence in his career. While upside remains, the substantial price tag and risky term are reasons why this deal is not Bowman’s best work.

Oct. 8, 2025

Terms: three years, $12 million ($4 million cap hit)

Despite Ekholm’s age, this contract is a positive signing for Bowman and the Oilers. It also kicks in this season, and while Ekholm will likely not be on their top pair in the second and third years of the deal (or even this season), the cap hit will not be punishing as the salary cap rises league-wide. Ekholm can also still provide offence as he showed last year, picking up 41 points.

Oct. 8, 2025

Terms: one-year, $1.5 million cap hit

Roslovic was added midway through the opening game of the 2025-26 season after the forward did not find the long-term deal he was looking for in the offseason. He proved to be a very solid middle-six scoring winger, picking up 21 goals and 36 points in 69 games. Despite Roslovic flaming out in the playoffs, this deal provided excellent value.

June 21, 2026

Terms: four years, $20 million ($4 million cap hit)

Acquired in the Mangiapane trade, Dickinson had a strong start to his Edmonton tenure and looked outstanding in the playoffs, despite fighting injuries and missing a few games. Locking up their shutdown centre was important, and this contract, like Ekholm’s, will prove to be very reasonable value down the line.

June 22, 2026

Terms: five years, $20.5 million ($4.1 million cap hit)

Signed with a similar mindset to Dickinson in locking up a defensively sound 2026 trade deadline acquisition, this deal will likely provide surplus value if Murphy can help solidify the penalty kill, which he had already begun to do at the end of last season. Although the penalty kill then became a mess during the playoffs, Murphy remained a steady presence while chipping in some offence.

July 1, 2026

Terms: five years, $20 million ($4 million cap hit)

Added shortly after the Darnell Nurse trade, this deal comes with some risk as Shea only has one full NHL season under his belt at 29 years old. The price tag, however, should be manageable if Shea does not live up to expectations and will become more than fair value should he continue to build off of last season with Pittsburgh, where he picked up 35 points and provided strong penalty-killing results.

July 1, 2026

Terms: one-year, $1 million cap hit

After an outstanding playoff run for Cup champion Hurricanes was cut short due to a knee injury, Edmonton added the Dane to a very inexpensive deal. Even with bonuses incorporated, which could see the contract being brought up to as high as $1.8m, the price tag remains low. Andersen will miss the start of the season with said knee injury, but he was brought in to be the starter when the playoffs roll around, and as long as he is ready and performing by then, this deal will be a win.

Bowman and his staff have made more smart decisions than poor ones when it comes to locking up players during his tenure. There are major misses like Mangiapane and Frederic, although the latter still has the opportunity to bounce back, but for the most part, the signings have been nice pieces of business.

Retaining players acquired by trade has also been good management. While time will tell how the contracts play out, it has made some steep acquisition costs more palatable.

Factoring in depth signings, adding talent from overseas, retaining two of the best players in the world, and the fact that even his worst misses haven’t been complete albatrosses like GMs before him, Stan Bowman’s contracts deserve an A- grade.

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