As Oilers fans, we love to debate and dissect the work of general managers. These are the people trusted and paid to build the team we see on the ice.

A huge part of that job is making trades: finding deals that improve your roster and, hopefully, push you closer to a Stanley Cup. Over the years, we’ve seen plenty of them. Some were brilliant, others still make us scratch our heads.

In this piece, I’ve looked back through franchise history and picked the best trade made by each Edmonton Oilers GM, from Glen Sather to Stan Bowman. You might disagree with some of these choices, and that’s fine. There have been plenty of trades that can spark debate in Oil Country.

Glen Sather was the architect of the Oilers dynasty in the 1980s. He wasn’t alone, but his leadership and hockey mind were major reasons the team won five Stanley Cups. Over two decades as GM, he made plenty of deals, but the one that stands out didn’t happen in the 1980s.

At the tail end of the 1992-93 season, Sather traded Esa Tikkanen to the New York Rangers for a prospect named Doug Weight. The young forward had just eight points in 13 games after joining Edmonton, but the team was coming off one of its worst seasons ever (26-50-8). The following year, Weight led the Oilers with 74 points, becoming a rare bright spot in the early ’90s.

By 1995-96, Weight hit the 100-point mark, something no other Oiler managed in that decade. He was named captain in 1999-00 and, by the time he was traded in 2001, had scored 178 goals and 436 points in eight seasons with Edmonton. No Oiler in the ’90s had more points (487) or goals (132).

Other strong Sather deals: acquiring Curtis Joseph and Mike Grier’s rights from St. Louis, getting Tommy Salo from the Islanders, and adding Jason Smith from Toronto. But none defined an era the way Weight did.

Replacing Sather after he left the Oilers to run the New York Rangers was no small task. Kevin Lowe made his share of controversial trades, but his best was landing Chris Pronger from St. Louis in 2005 for Eric Brewer, Doug Lynch, and Jeff Woywitka.

Fresh off the NHL lockout, Pronger instantly became a franchise-altering piece. He led the Oilers to the 2006 Stanley Cup Final, posted the third-best offensive season of his career, and had a dominant playoff run. Unfortunately, after the Cup Final loss, Pronger requested a trade and was dealt to the Anaheim Ducks.

A Hall of Fame defender during his playing career in Edmonton, Lowe has a mixed legacy as general manager. His work ahead of the 2006 deadline (adding Dwayne Roloson, Jaroslav Spacek, and Sergei Samsonov) is among the best string of in-season trades the league has ever seen. But losing franchise icon Ryan Smyth over pennies is an ugly memory for the Oilers.

Tambellini’s tenure was defined by a rebuild, and his record is thin on wins outside of the ones that came at the Draft Lottery.

His best trade came at the 2011 deadline, when he sent winger Dustin Penner to the L.A. Kings for Colten Teubert, a first-round pick, and a conditional third. That pick became Oscar Klefbom, who developed into a steady top-four defenceman and fan favourite before injuries cut his career short.

Without that trade, we don’t get the Klefbom era in Edmonton.

The MacT years weren’t exactly a high point for trades, but acquiring David Perron from St. Louis in 2013 was a solid move. Edmonton gave up Magnus Paajarvi and a 2014 second-round pick, and Perron responded with a career-best 28 goals and 57 points in his first season.

Though he was traded the next year to Pittsburgh for Rob Klinkhammer and a first-rounder, Perron was one of the few bright spots before the Connor McDavid era began.

Chiarelli’s time in Edmonton is remembered for more bad than good, but trading for Cam Talbot at the 2015 draft was a win. The Oilers sent second-, third-, and seventh-round picks to the Rangers for Talbot and a seventh.

Talbot became the starter for four seasons and backstopped Edmonton to its first playoff berth in a decade in 2016-17, starting 73 games with a .919 save percentage. His performance that year remains one of the best by an Oilers goalie in the last 20 years.

Holland inherited Connor McDavid and Leon Draisaitl in their prime and the mess left by Chiarelli. His best trade came in 2023, when he acquired Mattias Ekholm from Nashville for Tyson Barrie, Reid Schaefer, a first-round pick, and a fourth.

Ekholm stabilized the blue line, formed a dominant pairing with Evan Bouchard, and has been among the NHL’s best in plus-minus since joining Edmonton (+83). While the Cup hasn’t come yet, the Ekholm deal was a game-changer.

Holland also made undoubtedly the best free-agent signing in team history back in 2021, inking Zach Hyman to a seven-year deal.

Hired last summer, Bowman hasn’t had an opportunity to really put his stamp on the Oilers yet. That said, the former Blackhawks boss has already made a handful of solid additions during his brief time in Edmonton.

Bowman’s first year brought pressure to deliver at the 2025 deadline, and he struck by acquiring Jake Walman from San Jose for Carl Berglund and a conditional 2026 first-round pick. Walman isn’t Ekholm defensively, but he’s a reliable top-four defenceman with strong two-way metrics. The move surprised many, but Walman’s play has been well-received so far.

Being GM of the Edmonton Oilers means every move is under the microscope. When things go wrong, fans demand change. And with the franchise’s losing history, there’s no shortage of bad trades to point at. But through all the turbulence, each GM has had at least one deal that worked out for the team.

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