The Edmonton Oilers recently announced Stan Bowman as their general manager and executive vice president of hockey operations, following his reinstatement by the NHL.
This is Bowman’s first NHL role since leaving the Chicago Blackhawks GM position in Oct. 2021, making his return to the league just over two years after he was disciplined as a result of the Blackhawks’ sexual assault scandal. Bowman was aware of the occurrence but neglected to inform the proper authorities. Consequently, his hiring has not been well-received by the Oilers fan base, and rightfully so.
In exploring a little bit of the background of the Oilers’ new hire, Bowman served as the Blackhawks GM for 12 years, winning three Stanley Cups in 2010, 2013, and 2015. He’s been involved in many significant deals throughout his career and with that in mind, here’s a look at the top five largest contracts he’s negotiated and signed in his career, presented in the order they occurred.

Duncan Keith: 13-Year, $72 Million Contract Extension Signed in 2009

Former NHL D-man Duncan Keith was in his fifth season with the Blackhawks when he signed a 13-year contract extension worth $72 million on December 3, 2009, which, at the time, was the largest contract in team history. With Bowman overseeing the deal, the contract carried an annual average value (AAV) of $5.5 million.
Long-term deals in the 13-year range are now a thing of the past, and every contract carries some risk, but Keith’s deal, with a $5.5 million cap hit, turned out to be one of the better contracts of its era. The D-man was a cornerstone of the Blackhawks’ blue line for 11 seasons after signing the extension, helping the team win three Stanley Cups in total and he also won the Conn Smythe Trophy in 2015. All in all, Keith’s contract should be viewed as a win on Bowman’s résumé.
In 2021, the two-time Norris Trophy winner was 38 years old and sought a trade to be closer to his son in British Columbia. The blueliner waived his no-movement clause, and in July of that year, the Oilers acquired Keith and Tim Soderlund in exchange for Caleb Jones and a conditional 2022 draft pick.
Additionally, another possible win for Bowman was that he did not retain any salary when he traded Keith to Edmonton. However, a potential misstep might be in how he used the extra cap space (Seth Jones), which will be discussed later.
That said, Keith is now a player development coach for the Oilers. He played 64 regular-season games for the club during the 2021-22 season, recording 21 points and helping them reach the Western Conference Final. He was also noted for being a mentor to young D-man Evan Bouchard, who has since become one of the NHL’s most productive blue liners.
Nonetheless, there’s a little bit of irony in the fact that Bouchard, who was mentored by Keith (a player Bowman once signed to a lengthy contract), will now be seeking a new deal after the 2024-25 season—one that will also now be negotiated by Bowman.

Patrick Kane and Jonathan Toews: 8-Year, $84 Million Contract Extensions Signed in 2014

Patrick Kane and Jonathan Toews, once the marquee superstars of the Blackhawks and future Hall of Famers, had one more year left on their identical five-year, $31.5 million contracts that they had signed with the team before the 2010-11 season. That said, on July 9, 2014, they signed new identical contract extensions under Bowman’s watch.
The duo each signed an eight-year contract extension valued at $84 million, with an AAV of $10.5 million and it was also noted that Bowman sounded like a proud father at the press conference as he shared stories about his two forwards’ rise to stardom.
At the time, their agent indicated that both players could have commanded $13.8 million per season. This suggests Bowman did well in negotiations by signing them for $10.5 million AAV each, relative to their market value. On the other hand, there was also some concern that these contracts contributed to Chicago’s lack of cap space. Nevertheless, Kane and Toews, who helped bring three Cups to the franchise, became the first players to surpass the $10 million AAV mark since the salary cap was introduced in 2005.
That said, in trying to understand why the Oilers brought Bowman into the fold, one reason may be due to his experience negotiating massive contracts with superstars, such as the combined $168 million deals he previously negotiated for Toews and Kane. With Leon Draisaitl due for a contract extension and Connor McDavid also approaching one, his experience in this area could have been particularly appealing to the Oilers’ CEO of Hockey Operations, Jeff Jackson.

Brent Seabrook: 8-Year, $55 Million Contract Extension Signed in 2015

In September 2015, Bowman signed Blackhawks blueliner Brent Seabrook to an eight-year contract extension worth $55 million, with a $6.875 million AAV. At the time, the deal wasn’t regarded as a bad decision, as the Blackhawks’ defender was in his tenth season with the team, had been a key contributor to their three Stanley Cup wins, and was a leader on the backend, forming a great tandem with Keith on the top pair for many seasons.
Seabrook set a career-high in points, 49, in the season following the signing of his extension, but started to regress heavily thereafter as age and injuries took their toll. As the seasons went on, his play declined and he resembled more of a third-pairing D-man and unfortunately, by 2019, The Athletic ranked Seabrook’s contract as the worst in the NHL.
He was limited to 32 games during the 2019-20 season due to ongoing injuries, and a severe issue with his right leg ultimately ended his career at age 35. Mark Lazerus of The Athletic criticized Bowman’s decision-making on the Seabrook contract extension, saying:
“Stan Bowman was guilty of being too loyal to one of his most loyal players, and Seabrook spent the rest of his career getting mocked and jeered and booed and hated for it.”
Ultimately, the contract was Bowman’s way of rewarding Seabrook for past achievements, but it didn’t pan out as hoped. Moreover, because Seabrook didn’t officially retire, his contract remained on the Blackhawks’ books, on long-term injury reserve, until it expired last season.

Bowman Traded for Seth Jones and Signed Him to a $76 Million Contract in 2021

The moves Bowman made in July 2021 with the Blackhawks set off a chain reaction that affects his now Oilers team to this day.
At the time, perhaps in an attempt to keep his Chicago team contending, Bowman cleared cap space by trading Keith to the Oilers. He then traded Adam Boqvist, a first-round pick, and additional draft picks to the Columbus Blue Jackets in exchange for D-man Seth Jones and immediately signed him to a massive eight-year deal worth $76 million with a $9.5 million AAV in July 2021.
Signing Jones to such a large contract was a big gamble, as they were paying him as if he were going to be a perennial Norris Trophy contender, but he has not come close to achieving that level.
He set a career-high of 46 assists in his first season with the Blackhawks during the 2021-22 season. However, he also has a combined plus/minus of -90 over his past three seasons in Chicago, which can be partly attributed to the team’s rebuilding phase and partly to his performance.
Moreover, in 2023, The Athletic once again listed another Blackhawk, Jones, as having one of the worst contracts in the league, marking what could be another blunder by Bowman, who negotiated and signed the deal.
This brings us to the link between Bowman’s massive deal for Jones and how it connects to the Oilers.
Following the huge deal Jones signed, the Columbus Blue Jackets responded by signing their top D-man, Zach Werenski, to a six-year deal valued at $9.583 million AAV. Bowman set the market price for top D-men, which influenced the Oilers to sign Darnell Nurse to an eight-year deal worth $9.25 million AAV—a number that many now consider to be overpaid.
Overall, Bowman has experience negotiating and signing big money contracts. He’s been given a second chance with the Oilers, and it’s intriguing to see the parallels in his current situation. Just as he had superstars Kane and Toews with the Blackhawks, he now has Draisaitl and McDavid. Similarly, where he once had a stud D-man in Keith on defence, he now has Bouchard.
That said, Bowman’s major defining moments moving forward in Edmonton will be judged not only by his team’s success but also by how he handles the contract extensions (if he is able to) for those three key Oilers. Considering that, now that you’ve had some time to reflect on Bowman’s hire, what’s your stance on the Oilers bringing him on board?

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