The five worst Jim Benning trades: Vancouver Canucks' most damaging deals

The five worst Jim Benning trades: Vancouver Canucks’ most damaging deals

Jim Benning’s tenure as general manager of the Vancouver Canucks from 2014 to 2021 was marked by a series of questionable decisions that set the franchise back years. While Benning proved capable in the draft, his trade history tells a different story—one of mismanaged assets, premature abandonment of prospects, and a consistent pattern of overpaying for the wrong pieces. The consequences of these moves continue to impact the organization today, making it essential to examine the five worst Jim Benning trades that shaped the Vancouver Canucks’ struggles during his seven-year tenure.

These transactions didn’t just fail in isolation—they represented a broader problem with asset management that plagued the organization throughout the Benning era. From giving up future stars for marginal returns to trading away draft picks that became impact players, each deal on this list demonstrates why Vancouver missed the playoffs in five of Benning’s seven seasons as GM.

The Oliver Ekman-Larsson disaster that hamstrung the franchise

The Oliver Ekman-Larsson trade stands as perhaps the most catastrophic transaction in modern Canucks history. In July 2020, Benning acquired the aging defenseman along with Conor Garland from the Arizona Coyotes, sending back a package that included a first-round pick, a second-round pick, a seventh-round pick, prospect Jay Beagle, Loui Eriksson, and Antoine Roussel. More damaging than the assets surrendered was the albatross contract Vancouver took on.

Ekman-Larsson was signed through 2027 with an $8.25 million cap hit, one of the worst contracts in the NHL at the time. Arizona was so desperate to shed the deal they couldn’t afford to pay his salary on time. Instead of capitalizing on Arizona’s weak negotiating position, Benning actually gave up significant assets to take on the burden, essentially doing the Coyotes a massive favor while handicapping Vancouver’s cap flexibility for years.

The trade’s timing made it even worse. Benning was so fixated on acquiring Ekman-Larsson that he allowed veteran defenseman Chris Tanev to leave as a free agent rather than re-signing him. Tanev went on to be a stabilizing presence for Calgary and later Dallas, while Ekman-Larsson struggled to live up to his contract in Vancouver. His defensive metrics were among the worst in the league during his time with the Canucks.

While Garland provided some value as a productive forward, it wasn’t nearly enough to offset the damage done by Ekman-Larsson’s contract and the draft capital surrendered. The deal required a franchise-defining effort to eventually escape, and by the time the Canucks bought out OEL’s contract in 2023, the cap penalties were still affecting roster construction. This transaction perfectly encapsulated Benning’s worst tendencies: overpaying for name recognition, ignoring underlying analytics, and prioritizing short-term fixes over long-term sustainability.

Trading Jared McCann and picks for Erik Gudbranson’s toughness

In May 2016, Benning executed what would become his most regrettable trade when he sent 19-year-old forward Jared McCann, a second-round pick, and a fourth-round pick to the Florida Panthers for defenseman Erik Gudbranson and a fifth-round pick. The move exemplified Benning’s impatience with young prospects and his obsession with acquiring size and toughness at the expense of skill and potential.

McCann had just completed a promising rookie season with Vancouver, showing flashes of the first-round pedigree that made him the 24th overall pick in 2014. Rather than allowing him time to develop, Benning gave up on the young forward after just one season. The decision to include additional draft picks in the package—particularly a second-rounder—made an already questionable trade indefensible.

Benning’s rationale centered on building a tougher, more physical team to compete in the Pacific Division. He believed the 6’5”, 216-pound Gudbranson would provide the defensive presence and physicality the Canucks needed. The problem was that Gudbranson’s style of play was already becoming outdated in an NHL increasingly focused on speed and skill. His foot speed issues and inability to move the puck effectively made him a liability in Vancouver’s defensive zone.

Over his time with the Canucks, Gudbranson never developed into the top-four defenseman Benning envisioned. He struggled with injuries and was eventually traded to Pittsburgh in 2018 for a late pick and prospect. Meanwhile, McCann blossomed into exactly the type of player Vancouver desperately needed—a versatile, two-way forward capable of playing multiple positions. He’s since become a vital piece of the Seattle Kraken organization, regularly posting 20-plus goals and providing tremendous value. The second-round pick Vancouver surrendered became Rasmus Asplund, who carved out an NHL career of his own. Looking back at the broader context of the Canucks’ best and worst trades of all time, this deal stands out as particularly damaging to the franchise’s competitive window.

Gustav Forsling given away for Adam Clendening’s false promise

Less than eight months after selecting Gustav Forsling in the fifth round of the 2014 draft, Benning shipped the Swedish defenseman to the Chicago Blackhawks for Adam Clendening in February 2015. This trade represents the dangerous combination of impatience with prospects and overvaluing organizational depth over legitimate potential.

Forsling was admittedly a project when drafted, but he showed promising development in his junior career. At just 18 years old, he needed time to mature physically and refine his game. Benning, however, saw an opportunity to acquire Clendening, a 22-year-old former second-round pick who was lighting up the AHL and appeared NHL-ready.

The move seemed designed to add immediate organizational depth on defense, but it backfired spectacularly. Clendening played just 17 games for Vancouver during the 2014-15 season, spending most of his time in the AHL before being included in the trade package that brought Brandon Sutter to Vancouver. His NHL career never took off, and he’s played just 65 total games in the league.

Forsling, meanwhile, developed into exactly the type of defenseman every team covets in the modern NHL. After initially struggling to establish himself with Chicago, he found his game with the Florida Panthers, where he’s become a cornerstone of their blue line. His ability to move the puck, skate efficiently, and contribute at both ends of the ice represents everything the Canucks have lacked on defense during their recent struggles.

The trade hurts even more when considering Vancouver’s chronic shortage of quality left-shot defensemen. Forsling has played nearly 400 NHL games—almost double what Clendening managed despite being four years younger. He was also a key contributor to Florida’s Stanley Cup run, the type of playoff performer Vancouver desperately needed. This transaction exemplified Benning’s tendency to prioritize perceived readiness over legitimate upside, costing the organization a potential top-four defenseman for years to come.

The Tyler Toffoli rental that ended in organizational embarrassment

At the 2020 trade deadline, Benning made a significant push to bolster Vancouver’s playoff chances by acquiring Tyler Toffoli from the Los Angeles Kings for Tim Schaller, prospect Tyler Madden, a second-round pick, and a conditional fourth-round pick. On the surface, adding a proven 20-goal scorer seemed like a reasonable move for a team trying to make a deep postseason run.

Toffoli performed admirably during his brief stint with the Canucks, and the team made an unexpected run to the second round of the playoffs in the 2020 bubble. The trade could have been remembered as one of Benning’s better moves—except for what happened next. Vancouver completely fumbled the opportunity to re-sign Toffoli during the offseason, losing him to the Montreal Canadiens in free agency.

According to Benning’s own admission, the Canucks “ran out of time” to negotiate a contract extension with Toffoli. This explanation was met with widespread skepticism, especially after reports emerged suggesting Toffoli wanted to remain in Vancouver and was never even presented with a formal contract offer. The organizational mismanagement turned a potentially savvy acquisition into a disastrous rental that cost significant assets for just 20 regular-season games.

The aftermath stung even more as Toffoli immediately proved his worth in Montreal, scoring 28 goals in 52 games during the shortened 2020-21 season. He demonstrated exactly the type of finishing ability and veteran presence Vancouver desperately needed, making his departure feel like organizational malpractice. The assets surrendered in the trade—particularly Madden, a skilled prospect, and the second-round pick—represented real cost without any lasting return.

This transaction damaged Benning’s credibility both within the organization and across the league. It raised serious questions about Vancouver’s internal communication, contract negotiation capabilities, and overall strategic planning. Either way, trading meaningful pieces for 20 games of production exemplified the short-term thinking that plagued Benning’s tenure.

Brandon Prust for Zack Kassian and a pick: paying to downgrade

In July 2015, Benning sent Zack Kassian and a fifth-round pick to the Montreal Canadiens for Brandon Prust, a deal that made little sense at the time and looks even worse in hindsight. The transaction represented a puzzling downgrade at forward while simultaneously giving up a draft pick—the exact opposite of sound asset management.

Kassian had been acquired by Vancouver in 2012 as part of the Cody Hodgson trade with Buffalo. While he wasn’t lighting up the scoresheet with 59 points in 179 games, he was fulfilling his role as a physical presence who could protect teammates and occasionally contribute offensively. At 24 years old, Kassian still had room for development and was signed to a reasonable contract.

Prust, meanwhile, was 31 years old and coming off a disappointing season in Montreal. Benning believed the veteran’s experience and toughness would benefit Vancouver’s young roster, but the move ignored several red flags. Prust had just 15 points in 66 games the previous season, his physical style was taking a toll on his body, and his best years were clearly behind him.

The experiment failed miserably. Prust managed just one goal in 51 games with Vancouver and became a distraction off the ice with various controversies. He lasted just one season with the Canucks before being moved to waivers, and his professional career effectively ended the following year. The fifth-round pick Vancouver included in the deal added insult to injury—they paid Montreal to take Kassian off their hands.

While Kassian’s career had ups and downs after leaving Vancouver, he provided several productive seasons for the Edmonton Oilers, including a 15-goal campaign in 2019-20. More importantly, he continued to provide exactly what the Canucks thought they were getting from Prust: physical presence, toughness, and protection for skilled teammates. The trade highlighted Benning’s flawed evaluation process and his willingness to give up assets to “fix” problems that didn’t exist, all while creating new holes in the roster. For a team that has since struggled with lack of toughness and sandpaper, giving away Kassian and a pick to acquire a player who provided nothing represents a special kind of asset management failure.

How these five worst Jim Benning trades defined the Vancouver Canucks’ decline

The pattern across these five transactions reveals fundamental flaws in Benning’s approach to building a hockey team. He consistently overvalued intangibles like toughness and experience while undervaluing skill, youth, and potential. He demonstrated chronic impatience with prospects, giving up on players like McCann and Forsling long before they had reasonable opportunities to develop. Perhaps most damaging, he showed a troubling willingness to add draft picks to trades even when acquiring inferior players, effectively paying other teams to make Vancouver worse.

These deals didn’t occur in a vacuum—they represented a coherent philosophy that proved disastrous for franchise-building. While Benning deserves credit for his draft record, including selections like Elias Pettersson and Quinn Hughes, his inability to manage assets through trades repeatedly set the organization back. The long-term cap implications of deals like the Ekman-Larsson acquisition limited Vancouver’s flexibility to add complementary pieces, while the loss of players like McCann, Forsling, and Toffoli created holes that proved difficult to fill.

The Canucks are finally emerging from the shadow of these mistakes, but the process required years of rebuilding and salary cap gymnastics. New management has worked diligently to clean up the mess, buying out bad contracts and attempting to recoup some value from declining assets. The current competitive roster exists despite Benning’s worst trades, not because of them, serving as a reminder that poor asset management can set a franchise back for nearly a decade. For fans who endured the Benning era, these five transactions stand as cautionary tales about the importance of sound organizational philosophy and the lasting damage that poor trade decisions can inflict on an NHL franchise.