This marks Stan Bowman’s first full off-season at the helm of the Edmonton Oilers.

On July 24, 2024, the Edmonton Oilers hired Bowman as general manager. Before his arrival, Jeff Jackson handled several key tasks, including bringing in Viktor Arvidsson and Jeff Skinner, and re-signing Corey Perry, Connor Brown, Mattias Janmark, and Adam Henrique. To make room for those extensions, Jackson dealt Ryan McLeod to the Buffalo Sabres in exchange for Matthew Savoie.

While that opening stretch was strong enough to help the Oilers reach their second straight Stanley Cup Final, Bowman faced cap constraints almost immediately. When the St. Louis Blues extended offer sheets to both Philip Broberg and Dylan Holloway, Bowman responded by trading Cody Ceci to the San Jose Sharks for Ty Emberson. Edmonton then chose not to match the offer sheets. It was a misstep in Holloway’s case, but likely the right call with Broberg.

During the season, Bowman made a series of savvy acquisitions. He claimed Kasperi Kapanen off waivers, signed John Klingberg, and traded for both Trent Frederic and Jake Walman. All four players made an impact in the playoffs. That success prompts a fair question: how did Bowman handle the early off-seasons when he led the Chicago Blackhawks during their championship window from 2009-10 through 2017-18?

Let’s dig in.

Bowman was promoted to GM on July 14, 2009, a couple of weeks after the opening day of free agency. The team had already made a splash, signing Marián Hossa to a 12-year deal while letting go of Martin Havlát, Samuel Pahlsson, Matt Walker, and Nikolai Khabibulin (who signed a four-year deal with the Oilers).

It paid off. The Blackhawks won their first Stanley Cup since 1961, ending the league’s longest active drought at the time.

Fresh off their Cup win, the Blackhawks had to make tough cap-related decisions. They traded Dustin Byfuglien, Brent Sopel, Akim Aliu, and Ben Eager to Atlanta for Joey Crabb, Jeremy Morin, two draft picks, and Marty Reasoner. Reasoner was flipped before the season started. They also dealt Colin Fraser to the Oilers for a sixth-rounder and moved Kris Versteeg to Toronto in exchange for a package that included Viktor Stalberg.

On July 1, 2010, they sent Andrew Ladd to Atlanta for a marginal return. When Niklas Hjalmarsson signed an offer sheet with San Jose, Chicago matched it, but that decision forced Antti Niemi out, leading to Corey Crawford’s promotion.

The defending champions squeaked into the playoffs with 97 points in 2010-11, nearly upsetting Vancouver after falling behind 3-0 in the first round. Alexander Burrows ended the series with an OT winner in Game 7.

There were no major free-agent losses, but the Hawks signed veterans Jamal Mayers, Andrew Brunette, Sean O’Donnell, Daniel Carcillo, and Ray Emery. They traded Troy Brouwer to Washington for a first-rounder and dealt Brian Campbell to Florida for Rostislav Olesz. Steve Montador was acquired and later extended.

Crawford signed a three-year deal, and extensions were also handed to Patrick Sharp, Stalberg, Montador, and Michael Frolík. Brandon Saad inked his entry-level contract.

The 2011-12 season ended in disappointment: Chicago was eliminated in six games by the Coyotes, who won their first playoff series since moving to Arizona. The Coyotes would reach the Western Conference Final but haven’t made the playoffs in a non-COVID year since.

After back-to-back first-round exits, a shake-up seemed likely, but Bowman stayed the course. The Hawks’ lone trade was a minor draft-day move. They added Sheldon Brookbank, Michal Rozsíval, and Antti Raanta.

The lockout-shortened 2012-13 campaign saw the Blackhawks go 21-0-3 before their first regulation loss. At the deadline, they added Michal Handzuš. They cruised through Minnesota, Detroit, and Los Angeles before defeating Boston in six games in the Final, winning their second Stanley Cup in four years.

Bowman was active: he traded Dave Bolland to Toronto, Michael Frolík to Winnipeg, and Daniel Carcillo to Los Angeles, all for picks. Emery, Stalberg, and Olesz left in free agency.

To fill holes, the Blackhawks re-signed Nikolai Khabibulin and added Theo Peckham and Brad Winchester. They also handed out extensions to Bickell, Leddy, Handzuš, and Rozsíval.

Chicago finished third in the Central in 2013-14, knocked out St. Louis and Minnesota, and fell to the eventual Cup champion Kings in a legendary seven-game Western Conference Final.

A relatively quiet off-season saw only one major move: Brandon Bollig was traded to Calgary for a fourth-round pick. Bowman later acquired Antoine Vermette ahead of the 2015 deadline.

Signings like Brad Richards, Cody Bass, Kyle Cumiskey, Carcillo, and Erik Gustafsson proved useful. The Blackhawks finished third in their division in 2014-15, eliminated Nashville, Minnesota, and Anaheim, and defeated Tampa Bay in the Final to win their third Cup in six seasons.

Looking to repeat, Chicago was again squeezed by the cap. Bowman traded Raanta to the Rangers, Brandon Saad to Columbus for Artem Anisimov, Sharp to Dallas for Trevor Daley, Nilsson to Edmonton, and Versteeg to Carolina. Richards, Vermette, Bass, and Oduya departed in free agency.

They signed Viktor Tikhonov, Cameron Schilling, and Mike Liambas on July 1, but the real gem came earlier: on May 1, during their Cup run, Bowman signed undrafted Russian winger Artemi Panarin. He went on to post 30 goals and 77 points as a rookie, beating Connor McDavid for the Calder Trophy.

Chicago again placed third in the Central in 2015-16, but lost to St. Louis in seven games in the first round.

Bowman sent Teuvo Teräväinen and Bickell to Carolina for picks and moved Andrew Shaw to Montreal. Free-agent losses included Andrew Ladd (Islanders) and Dale Weise (Flyers). The team signed Brian Campbell, Sam Carrick, Spencer Abbott, and Jordin Tootoo.

Despite finishing with 109 points (tops in the West), Chicago was swept in the first round by the eighth-seeded Predators. Nashville made it to the Final, where they lost to the Penguins, the NHL’s first repeat champs since the late-’90s Red Wings.

Bowman’s biggest misstep came here: he traded Artemi Panarin, Tyler Motte, and a sixth-rounder to Columbus for Brandon Saad, Anton Forsberg, and a 2018 fifth-round pick. He also traded longtime defender Hjalmarsson to Arizona for Connor Murphy.

Oduya left in free agency (again), and the only notable signing was Patrick Sharp’s return.

With the core aging and asset management slipping, Chicago missed the playoffs for the first time in a decade. Aside from beating the Oilers in the 2020 play-in round, they haven’t been back since.