No team ever walks out of the offseason thinking their big addition will end up being a bad move. Otherwise, they would not have acquired the player in the first place.
But often it does not take long for that buyer's remorse to kick in when the puck drops and a team sees how that new addition fits on their roster and actually plays for them.
A lot of times, that big free-agent addition is a buyout or trade waiting to happen. Sometimes the player a team gave up in a trade blossoms, while the player they acquired doesn't work out. That is the risk teams take in a lot of these moves.
We take an early look at teams that might be already having second thoughts about their additions.
Edmonton Oilers: Signing Jack Campbell
Goaltending has been a major issue for the Oilers for most of the Connor McDavid era. General manager Ken Holland made a meaningful effort to improve that this offseason when he signed Campbell to a five-year, $25 million contract in free agency to take over their top goalie spot.
There is always a risk with long-term contracts in free agency for goalies, and Campbell seemed especially risky because he does not have an extensive track record of consistent success in the NHL.
Another red flag: Another Stanley Cup contender (Toronto) decided he was not worth that price and they needed to upgrade the position.
Campbell has been a solid backup, and he showed flashes of potential during his time as a starter in Toronto. But he turns 31 in January, and few would be able to say how good of a goalie he actually is with any confidence. There is always a significant risk in trying to project future goaltending performances because the position can be so maddening, and making that sort of investment in a player who has no extended track record as a high-level starter is quite the roll of the dice.
Campbell has had a rough start with the Oilers, managing only a .874 save percentage in his first eight appearances, and he has been outplayed by backup Stuart Skinner.
The Oilers are pushed to the top of the league's salary cap and do not have the flexibility to miss on free agents at this important of a position. They better be right about Campbell. Early returns are not promising.
Toronto Maple Leafs: Matt Murray Trade
This might be unfair because Murray has only played in one game and been sidelined with an injury, but that is sort of the problem with Toronto's decision to take on Murray's contract.
He has not only regressed from where he was in his first two years when he was a back-to-back Stanley Cup champion with the Pittsburgh Penguins, but he has also missed a lot of time to injury recently.
This was always a curious decision by Toronto.
The Maple Leafs are under immense pressure to have postseason success and desperately needed to find a strong solution in goal. Murray has not been one of the league's least productive goalies over the past three years, but he carries a $6.25 million salary cap hit for this season and next season. For a team that is pushed to the limits of the salary cap, that is a huge commitment to take on.
Given the questions surrounding Murray, as well as the way some of their other potential offseason options (Darcy Kuemper, Ville Husso, Alexandar Georgiev) are playing, it would not be wrong for the Maple Leafs to have some regrets.
Especially during what has been a really disappointing start to the season for the team overall.