The five riskiest (and worst) signings from the first day of NHL free agency

The NHL's free-agent signing period officially opened on Saturday, and it did not take long for teams to start throwing around some silly money.

There is always a risk in dipping into the free-agent market because you are typically bidding for players other teams decided they did not want, but it never stops teams from going wild as soon as they can.

Let's take a quick look at five of the riskiest (and worst) contracts signed on the first day of the signing period. 

Alex Killorn to Anaheim Ducks

The deal: Four years, $25M

Killorn has been an excellent player for the Tampa Bay Lightning and was a key cog in the team's four Stanley Cup Final appearances dating back to 2014. He is also coming off a strong 2022-23 campaign that saw him score 27 goals.

The risk here -- and the problem -- is that Killorn is going to be 34 years old when the 2023-24 season begins, and his best days are almost certainly behind him. There is a very good chance that within a year or two the Ducks are looking at this contract with some serious regret if and when his production drops. 

Tristan Jarry back to Pittsburgh Penguins

The deal: Five years, $26.875M

Jarry has been the Penguins' starting goalie for the past four seasons and it seemed to be a foregone conclusion his time with the team would end in free agency. Injuries and inconsistency made him one of the organization's biggest question marks and there just did not seem to be a path for him to return.

Until there was.

The Penguins not only brought him back but gave him a five-year deal to remain their starting goalie.

When Jarry has been healthy, he has played well at times in his career, even earning two All-Star game nods. But injuries have been a constant problem for him the past two years and have severely limited his impact. The Penguins are betting he can stay healthy and find some consistency, while also clearly believing there was no better upgrade available. It is a huge risk. 

Joonas Korpisalo to Ottawa Senators

The deal: Five years, $20M

The Senators had one of the worst goalie situations in the NHL last year and it was a big reason why they missed the playoffs. 

It needed to be one of their top priorities this offseason and they addressed it by signing Korpisalo to a long-term deal.

The risk here is simply that nobody really knows how good Korpisalo actually is and Ottawa is committing to him for the next five years as their starter. He has had moments where he has looked good -- including during the 2022-23 season -- but he has finished with a league average or better save percentage in just three of his eight seasons in the NHL. Projecting goalies is always a risk and the Senators are taking a huge one here. 

Pierre Engvall re-signing with New York Islanders

The deal: Seven years, $21M

This is a classic case of "I like the player but I hate the contract." 

There is nothing wrong with the Islanders keeping Engvall on the roster and wanting to re-sign him. The $3M per year salary-cap figure is also perfectly acceptable for what he provides offensively and defensively. 

But he is still only a depth player who is not going to make a major impact. You simply do not need to sign players like that for seven years. 

Ryan Reaves to Toronto Maple Leafs

The deal: Three years, $4.1M

Is it going to cripple the Maple Leafs' salary cap situation? No. Does he make them dramatically worse? Also no. He also does not make them much better. 

Reaves is an enforcer, a player whose greatest contributions are fighting people, delivering some big checks and nothing more. He is also going to be 37 years old this coming season and is very much at the end of his career. It is just a bizarre move for a team that needs to add more scoring depth to its roster. Not a fighter.