Tyson Barrie recently announced his retirement from the NHL after 14 seasons and 822 career games, many as an effective offensive defenceman and occasional power-play quarterback. With over 500 career points, he enjoyed five seasons of more than 50 points and seven seasons of double-digit goal totals. But, despite his impressive resume, his one season with the Toronto Maple Leafs wasn’t among his career highlights.
Barrie will inevitably be remembered as a key part of the underwhelming return when the organization traded Nazem Kadri to the Colorado Avalanche. The 2019 offseason deal saw Toronto ship out the sometimes temperamental and undisciplined Kadri for a dynamic blueliner in Barrie and a speedy middle-six forward in Alex Kerfoot. Unfortunately, the club lost a heart-and-soul player for an underwhelming return.
In NHL markets like the Avalanche and Edmonton Oilers, Barrie may be celebrated for his contributions. Here, however, we will use the veteran defenceman’s retirement to explore where the Kadri-for-Barrie (and Kerfoot) trade ranks among the franchise’s worst over the past decade*. These are the Maple Leafs’ five-worst trades of the past 10 years:
*Note: We are considering all trades made as of the summer of 2015 and onward.
Dishonorable Mention
Several recent bad deals didn’t make the top five. The Dion Phaneuf era ended with a whimper when the former captain was traded in February 2016 for four players and one draft pick who would play just 54 total games in Toronto. However, Phaneuf’s subsequent tenure with the Ottawa Senators and Los Angeles Kings was just as underwhelming as what Jared Cowan, Colin Greening, Milan Michalek and Tobias Linberg offered the Maple Leafs.
In another disappointing trade with the Senators that centred around a defenceman, Cody Ceci became a target of Maple Leafs fans’ ire after the 2019 deal that brought him to Toronto for Connor Brown, Nikita Zaitsev and Michael Carcone. Apart from giving up a useful forward in Brown, the Maple Leafs didn’t lose much here, apart from some fans’ hair as they watched Ceci’s numerous defensive miscues.
Finally, Toronto paid handsomely to land Ryan O’Reilly at the 2023 Trade Deadline, shipping out four draft picks and minor leaguers Mikhail Abramov and Adam Gaudette for the hometown star. O’Reilly was excellent for Toronto, but the draft capital sacrificed was probably a little too steep for what amounted to 13 regular-season and 11 playoff games.
5) Maple Leafs Land Nick Foligno
| Toronto Maple Leafs Get: | Columbus Blue Jackets Get: | San Jose Sharks Get: |
| Nick Foligno | 2021 First-Round Pick | 2021 Fourth-Round Pick |
| Stefan Noesen | 2022 Fourth-Round Pick |
Acquired two seasons apart, there are plenty of similarities between the trades for O’Reilly and Nick Foligno. Both veteran forwards were brought in to provide leadership, character and toughness along with on-ice production. But while both proved to be costly rentals who didn’t help the Maple Leafs reach new heights before signing elsewhere, at least O’Reilly was a productive member of the club.
At the cost of a first-round pick and two fourth-round selections, Toronto got a mere four points (and no goals) in seven regular-season games and one assist in four playoff games out of Foligno. In hindsight, the Maple Leafs couldn’t reasonably have expected much more from the then-33-year-old. He only had seven goals in 42 games to date that season and had managed just 10 goals in 67 games the previous campaign.
But the acquisition cost wasn’t cheap. The Maple Leafs sent out three draft picks, most notably the 25th overall selection in the 2021 Draft, which was used to bring in Corson Ceulemans. The fact that the 22-year-old blueliner has been a disappointment to date in the Columbus Blue Jackets’ organization doesn’t make Toronto’s asset management any better.
4) Maple Leafs Trade Mason Marchment
| Toronto Maple Leafs Get: | Florida Panthers Get: |
| Denis Malgin | Mason Marchment |
In what was perhaps the most damming example of former GM Kyle Dubas’ emphasis on skill over size and physicality, the club made a minor league deal in the days leading up to the pandemic, acquiring Denis Malgin from the Florida Panthers for Mason Marchment.
We covered this trade in-depth a few months ago on its fifth anniversary. Malgin managed just two goals across 31 games with the Maple Leafs and never really established himself in the NHL before returning home to Switzerland. Marchment, meanwhile, has blossomed into an impact power forward, coming off back-to-back 22-goal seasons with the Dallas Stars before joining the Seattle Kraken.
Dubas had seen plenty of Marchment at the American Hockey League (AHL) level with the Toronto Marlies and clearly considered the diminutive-but-speedy Malgin as the better long-term bet. Unfortunately, it only took until the 2021-22 season for the Uxbridge, Ontario native to emerge as a bona fide force, breaking out with 18 goals and 47 points in 54 games with the Panthers. With questionable depth on the left wing behind Matthew Knies, the Maple Leafs would have done well to keep Marchment around.
3) The Phil Kessel Era Ends in Toronto
| Toronto Maple Leafs Get: | Pittsburgh Penguins Get: |
| 2016 First-Round Pick | Phil Kessel |
| 2016 Third-Round Pick | 2016 Second-Round Pick |
| Kasperi Kapanen | Tyler Biggs |
| Scott Harrington | Tim Erixon |
| Nick Spaling |
Phil Kessel’s up-and-down six-year tenure with the Maple Leafs finished with the club riding a dismal 30-44-8 record to a seventh-place finish in the Atlantic Division. In short, the split between Toronto and the NHL’s current ‘iron man’ was inevitable – both to help the club transition to a new era and to give the then 27-year-old a fresh start elsewhere. But did they really need to help him out as much as they did?
Kessel was sent to the Pittsburgh Penguins in a blockbuster deal involving six players and three draft picks. For the Maple Leafs, the trade helped initiate a rebuild that ultimately yielded the current era of perennial playoff contention. However, the deal itself failed to deliver much value.
The first-round pick was shipped out in the Frederik Andersen trade (and became Sam Steel), the third-round pick (James Greenway) never reached the NHL, and neither Nick Spaling nor Scott Harrington left a mark in Toronto. Kasperi Kapanen enjoyed several productive seasons with the team, including a 20-goal campaign, but it’s hard not to be a little underwhelmed by the overall return.
This trade looks especially paltry when you consider how Kessel fared in the aftermath. The speedy, high-scoring winger was the Penguins’ missing piece alongside Sidney Crosby and Evgeni Malkin, helping deliver back-to-back Stanley Cups as soon as he arrived in Pittsburgh. He even enjoyed a renaissance 2017-18 campaign, with 34 goals and a career-best 92 points.
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2) Maple Leafs Ship Out Nazem Kadri
| Toronto Maple Leafs Get: | Colorado Avalanche Get: |
| Tyson Barrie | Nazem Kadri |
| Alex Kerfoot | Calle Rosen |
| 2020 Sixth-Round Pick | 2020 Third-Round Pick |
As with Mitch Marner, Kadri often served as the scapegoat for fans during his time with the Maple Leafs. The hot-headed forward had trouble keeping his emotions in check, usually with significant consequences. The seventh overall pick of the 2009 NHL Draft incurred suspensions in back-to-back postseasons on account of dirty hits, putting his team in a precarious position in the season’s biggest moments.
While that temper and lack of self-control expedited Kadri’s exit from the organization, the club probably didn’t put enough emphasis on the positive side of that passion. The former London Knight brought a level of heart and soul to the franchise that has been difficult to replace. Both Barrie and Kerfoot had their moments with the Maple Leafs but lacked Kadri’s inspired energy and drive. Like Kessel, it was difficult to watch their former draft pick hoist the Cup as part of the 2022 Colorado Avalanche – even if his penchant for ill-timed playoff suspensions followed him to the Mile High City.
There is a valid argument to be made that trading Kadri was both necessary and, in many ways, beneficial. After all, Toronto’s only series wins of the past two decades have come in the time since he left. Unfortunately, though, Barrie never became the top-pairing defenceman that the club had hoped to acquire, and Kerfoot capped out at 13 goals and 51 points as a decent middle-six forward. Kadri, meanwhile, has continued to make an impact in Colorado and with the Calgary Flames, with some fans still clamouring for a potential reunion.
1) Maple Leafs Let Carter Verhaege Get Away
| Toronto Maple Leafs Get: | New York Islanders Get: |
| Michael Grabner | Carter Verhaege |
| Taylor Beck | |
| Matt Finn | |
| Christopher Gibson | |
| Tom Nilsson |
There has been some seller’s regret over trading away Marchment, Kessel and Kadri, but no player has come back to haunt the Maple Leafs quite like Carter Verhaege. A local kid and 2013 third-round draft pick, Verhaege didn’t necessarily have the profile of a future impact player for a Stanley Cup champion when he was shipped out with four other mid-range prospects for Michael Granlund ahead of the 2015-16 season. However, his key role on the juggernaut Panthers and his success against the Maple Leafs have made what was already a bad trade look disastrous.
None of Verhaege, Taylor Beck, Matt Finn, Christopher Gibson or Tom Nilsson were considered major losses when the trade took place. To be fair, only Verhaege proved costly. Beck saw action in 92 NHL games, and Gibson got 16 games in net, but the quartet otherwise failed to make any kind of impact. But the risk of surrendering quantity is that there are more opportunities for at least one prospect to pan out.
Verhaege, who bounced around the New York Islanders and Tampa Bay Lightning before landing with the Panthers, has recorded 120 goals over his last four seasons. He also has a whopping 44 points (including 18 goals) over Florida’s past two Cup runs. In contrast, Granlund lasted one season in Toronto, scoring nine goals in 80 games and helping the Maple Leafs go from a 68-point team that finished seventh in the Atlantic to becoming a 69-point team that finished eighth.
Mercifully, none of these misguided deals were quite on the level of Niedermayer-for-Kurvers or even Rask-for-Raycroft (in 2006). Still, even in a decade filled with a relatively high level of organizational success, you can point to many examples in which the Maple Leafs’ front office failed to either acquire the right player, maximize their return or understand the value of what they were trading away.
