The 5 Worst Toronto Maple Leafs Free Agent Signings in the Auston Matthews Era

During the Toronto Maple Leafs rise to prominence in the Auston Matthews era, they had many opportunities during almost the past decade to look for ways to bolster the roster in support of the Leafs superstar and company.

The Toronto Maple Leafs had explored the trade route, making both good and not-so-good deals to address their needs in the process. In addition, they have also tried promoting some young prospects from within their organization where some showed promise and potential, whereas others ultimately flamed out in the end.

But most importantly, the Leafs made most of their major moves during free agency, with hopes that they could add solid, proven commodities that could significantly help the team get to the next level without giving up any assets.

Some of the Maple Leafs signings may have worked out in one way or another. However, there have been various others where the Leafs probably wished they had spent their money more wisely instead.

The 5 Worst Toronto Maple Leafs Free Agent Signings in the Auston Matthews Era

With the 2024 NHL free agency set to open in a little more than two weeks away, let’s take a look back at five free agent signings by the Maple Leafs since the debut of Matthews in 2016 that unfortunately didn’t produce the results that was expected of them in the end.

Patrick Marleau

With the new wave of talent leading the way in Matthews, Mitch Marner and William Nylander, the Leafs suddenly found themselves back in strong contending status after getting back into the playoffs during the 2016-17 season.

With everyone’s hopes and expectations suddenly raised to another level, it encouraged the Leafs to make a big splash during free agency that year to further augment the new star-studded lineup.

As a result, the Leafs decided to put most of, if not all of their marbles into the most durable NHL player of all-time in Patrick Marleau by signing him to a three-year contract with a $6.25 million AAV.

Turning already 38 by the start of the 2017-18 season, many were afraid that the contract wouldn’t age well despite Marleau being one of the most prolific scorers in the game. He had a decent first year with the Buds as he potted 27 goals and 20 assists for 47 points in 82 games played, while adding another four goals during the playoffs.

However, his game regressed considerably during his second year with the team, so much that he was deemed expendable and was eventually traded away to the Carolina Hurricanes along with a first-round draft pick for cap relief following the 2018-19 season.

The addition of Marleau wasn’t a complete failure. After all, he did bring some valuable veteran leadership to the young Leafs core and played some role in getting them into the playoffs. As a result, the signing was bad not because of Marleau’s underwhelming performance.

But with most of the young stars on team-friendly, entry-level deals, the Leafs could have spent the money better to give the team the best and strongest chance of winning the Stanley Cup. Instead, it was mostly blown on Marleau, who eventually led the Leafs to just two first round exits.

On top of that, they even had to give up a valuable asset by throwing in a first round pick to unload his albatross of a contract in the end.

Joe Thornton

The Leafs surely didn’t learn from their mistake with Marleau when they decided to bring more veteran leadership in grey-bearded superstar Joe Thornton through free agency prior to the start of the 2020-21 NHL season.

Had Toronto signed him at least 10 years prior in his prime, no doubt he could have been a huge difference maker. But at aged 41 entering the season at the time, many probably knew it wasn’t going to happen with Father Time out in full force.

Surprisingly, Thornton did appear to hold his own in the early parts of the season when he tallied 3 goals and 8 assists in his first 12 games while playing together with the likes of Matthews and Marner.

However, things practically went downhill from there in terms of production as he would only register another 9 points for the rest of the year, including going pointless during a rough 17-game stretch in the middle part of the season.

Thornton’s foot speed obviously was no longer there, making it difficult for him to catch up with the high-flying young Leafs core.

As a result, he was eventually moved further down in the lineup to the bottom-six as the season progressed and ultimately provided little to no Impact when the playoff season came around.

Looking back, getting Thornton seemed like a great idea, that is, had it been perhaps a decade earlier. Instead, the Leafs wasted a potential valuable spot in the lineup that could have helped the team..

Nick Ritchie

With the Leafs unable to afford to bring back fan favourite Zach Hyman following the 2020-21 season, the team searched for his ideal replacement during free agency that offseason.

After seeing Nick Ritchie put up a career-high 15 goals with the Boston Bruins just the previous year, the Leafs decided to give the former first-rounder a chance to play with Matthews and Marner on the top line for 2021-22 by signing him to a two-year, $5 million contract. At 6-foot-3 and 236 pounds, Ritchie was certainly bigger and stronger than Hyman and was excepted to be a more dominant force than his predecessor..

However, once the regular season rolled around, the Leafs quickly found out Ritchie was nothing close to what Hyman was during his time with the blue and white.

Very often, Ritchie seemed out of position and failed to use his size to dominate the opposition. Even worse was the fact that he had practically no chemistry with Matthews and Marner, which was kind of hard to comprehend, considering the tremendous skills and abilities of the dynamic duo. Ritchie ended up registering just 2 goals and 7 assists in 33 games as a Leaf, and was ultimately traded in-season to the Arizona Coyotes for Ryan Dzingel and Ilya Lyubuskin.

Consequently,, the Ritchie signing had turned into a complete bust as he couldn’t even survive the season. But given that Lyubuskin did play a more major role on the Leafs defense for the rest of the 2021-22 season, at least Toronto managed to recoup a useful asset for their failed experiment.

But if the Leafs had the chance to do it over again, perhaps they should have done everything they could to re-sign Hyman instead, given the successful prolific scorer that he has now evolved into with the Edmonton Oilers.

John Klingberg 

Alas, even in the Brad Treliving era as GM in Toronto, he has already registered a “miss” to his record in terms of free agent signings.

During the past offseason in 2023, Trelviing wanted to add a proven right-handed defenseman to help bolster the Leafs defensive corps’ offensive potential heading into the 2023-24 season.

As a result, the Leafs decided to ink veteran John Klingberg to a one-year, $4.15 million deal.

However, there were already red flags in his resume as his defensive play had regressed quite considerably in recent years.

Nevertheless, the Leafs believed that he could more than make up for it by being a major contributor offensively and by helping to quarterback their potent power play. Unfortunately, Klingberg would wind up being a huge disappointment for the Leafs as he struggled big time both offensively and defensively right from the start of the 2023-24 regular season.

Klingberg ended up appearing in only 14 games, with only five assists to show for while registering just two points on the power play. (All stats from hockeydb.com)

Klingberg’s season and eventual tenure with the Leafs would ultimately end when he had to undergo hip surgery in December.

So much for one of their huge investments from the offseason. Tyler Bertuzzi and Max Domi might have ended up being solid producers in the end for the Leafs after a rough start, but the Klingberg addition certainly turned out to be a complete failure.