2 of the 5 Worst UFA Signings This Summer Were Ex Toronto Maple Leafs

The Toronto Maple Leafs, comparably, did pretty good!

Toronto Maple Leafs v Philadelphia Flyers
Toronto Maple Leafs v Philadelphia Flyers / Mitchell Leff/GettyImages
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Most of the free agents are off the board now and it looks like the Toronto Maple Leafs are done adding to the roster on the free-agent market.

Many opinions have been put out there about the Toronto Maple Leafs new acquisitions however, I want to focus on signings around the league.

Over a billion dollars was thrown around on July first and as usual, on July first, some bad deals were handed out.

This list of the five worst signings so far isn't going to be in any particular order. Some of the things I looked at when deciding on the five worst deals were money and term but I also looked at the fit for the player as well as the organization.

Joel Edmundson

Joel Edmundson signed a four-year deal with an average annual value of 3.85 million dollars with the LA Kings (All salary statistics from Capwages.com).

The former Leaf can play both the left and the right side and is a defensively focused defenseman. He struggles with footspeed but will be a physical presence on the backend for the Kings.

This deal was head-scratching for me. I'm struggling to see what General Manager Rob Blake was thinking with this signing. The Kings lost Matt Roy this offseason, who is a good two-way defenseman and a strong skater.

With that tough loss on the blueline, they decided to give way too much term as well as too much money to a 31-year-old Joel Edmundson who has also struggled with injuries throughout his career. While he can play both the left and right side as well as the penalty kill, he can't really skate or move the puck.

This deal reminds me of the four-year contract with an AAV of four million dollars the Blue Jackets signed Erik Gudbranson to in the 2022-23 offseason.

Ilya Lyubushkin

Another former Leaf makes the list. Lyubushkin signed with the Dallas Stars on a two-year deal with an AAV of 3.25 million dollars.

Lyubushkin was traded from Anaheim to the Leafs at the deadline and the Leafs got him making less than the league minimum against the cap due to having double salary retention in the deal.

Even then, I wasn't excited about the trade.

Lyubushkin is a stay-at-home defenseman who scares me with the puck on his stick but is another physical presence on the ice.

It is a shorter term deal which makes it more tolerable than the Edmundson deal and Lyubushkin is also a right-hand shot. Typically, you have to pay more for the right-hand shot defenseman.

The Stars lost Tanev in the offseason who was spectacular for them after acquiring him last deadline.

While it was always going to be tough to replace him, this Lyubushkin deal as well as another signing they made which I will get to was head-scratching.

The Stars are a very well-run organization but outside of the one-year deal worth three million dollars they gave to Matt Duchene, their offseason has been head-scratching.

Matt Dumba

The other Stars signing I wanted to touch on was Matt Dumba's signing, a two-year deal with an AAV of 3.75 million.

Dumba was a deadline acquisition for the Tampa Bay Lightning last season and he struggled at the start of the season with Arizona as well as when he got to Tampa.

In Dumba's prime, he was a solid offensive defenseman who wasn't afraid to throw his body around.

However, his point totals have been declining and he is a liability in his own end. He only posted 12 points in 76 games last season between Arizona and Tampa.

His underlying numbers weren't any better. Through 58 games in Arizona, he lost his minutes where he had a goals-for percentage of 43.84 percent and it was even worse in his 18 games in Tampa, where his goals-for percentage was at 38.05 percent (Stats from EvolvingHockey.com).

The money they handed to Dumba is bad but adding him as well as Lyubushkin is even worse.

Chandler Stephenson

Stephenson signed in Seattle on a seven-year deal with an AAV of 6.25 million.

Stephenson was a big part of the Vegas Cup run in the 2022-23 season, where he posted 20 points in 22 games. Last season he only posted 16 goals and 35 assists for 51 points in 75 games (All point totals from NHL.com). 

Since Seattle's inaugural season, they have been a team with a lot of good support players but no top talent on the roster.

Stephenson doesn't change this and they're paying him 6.25 million a year.

Last season, Stephenson only had an expected goals for per 60 of 2.44 and an expected goals against per 60 of 2.56. Right now, DailyFaceoff.com has him projected as the second-line centre behind Matty Beniers.

Beniers faced his sophomore slump last season. He had a 20-point drop-off between his rookie year and last season. 

Stephenson will be 37 when the deal expires and even with the cap going up, I don't see how he will be worth 6.25 a year.

Stephenson is a good player and the Leafs had interest in signing him, but obviously backed down when things started to get crazy.

This is far and away one of the NHL's worst contracts.

Sean Monahan

Monahan signed with the Columbus Blue Jackets this offseason on a five-year deal with an AAV of 5.5 million dollars.

Monahan was a good story last season but this is a terrible contract anyways.

Coming off a major injury, the 29-year-old posted 26 goals and 33 assists for 59 points in 83 games between his time in Montreal as well as Winnipeg. This was remarkable for a guy who has an injury history, but it doesn't justify a five-year commitment.

His point totals were respectable and he's solid in his own end. I like Monahan as a player but at this point in his career, Monahan is a support player who is a decent option as a third-line centre.

I'm assuming part of this deal is to try to get his former teammate Johnny Gaudreau going after back-to-back pretty disappointing seasons for him.

5.5 million for Monahan is too expensive and five years to a guy with significant injury history in his career gives this deal a decent chance to age poorly.

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Even with the cap rising if the injury bug continues to affect him, it will probably still be tough for him to live up to the cap hit.

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