Andrew MacDonald

Nearly every team has one of those players: a top talent they were excited to sign and never thought could do anything but help them. In hindsight, history shows that more often than not, expensive, long-term free agent contracts don’t work out. It may look good at first (or it may look bad right away to the outside observer), but players struggle to make their value last throughout a lengthy contract. Those contracts come back to bite teams and are hard to get rid of. As teams begin to finalize their rosters at this point in the off-season, many are struggling to make everyone fit under the salary cap and are regretting these past signings that exasperate a cap crunch that can be tough for even a mistake-free club. We already took a look at the first third and second third of the league; here are the contracts that each of the final ten teams would most like to trade, from Philadelphia to Winnipeg:

Philadelphia Flyers: Andrew MacDonald – two years, $10MM remaining

Based purely on salary versus what he brings to the table, Jori Lehtera’s $4.7MM contract is the worst on the Flyers. However, Philadelphia is far from cap trouble this season, currently among the five lightest payrolls in the league, and Lehtera’s deal expires after this season. However, next year the Flyers will need to re-sign or replace Wayne Simmonds, hand new deals to Ivan Provorov and Travis Konecny, and likely find a new starting goalie. The cap crunch will be much more real and the over-inflated $5MM contract of Andrew MacDonald will hurt. MacDonald’s six-year, $30MM contract was immediately panned by the public and it wasn’t long after that he was buried in the minors for cap relief and to keep him out of the lineup. MacDonald simply is not the player he was with the New York Islanders earlier in his career when he could eat major minutes, was stellar in man-to-man defense, and could block shots with the best. What he is being paid now is far beyond what he is actually worth. Some would say that Radko Gudas is worse, but that is an argument that suffers from recency bias. Combining the past two seasons, Gudas actually has the same amount of points as MacDonald in fewer games and less ice time, a better plus/minus rating, far more shots, and of course infinitely more hits. At $3.35MM for the next two years, Gudas is a far better deal.

Pittsburgh Penguins: Carl Hagelin – one year, $4MM remaining

The real answer is that GM Jim Rutherford would not like to trade any more players. He already ditched two of his worst contracts by sending Matt Hunwick and Conor Sheary to the Buffalo Sabres and he isn’t eager to make another salary dump. However, the reality is that Rutherford is going to find it hard to manipulate his roster this season with just over $1MM in cap space. As such, it is likely that another Penguin could be on the move. An outside observer could easily point to the Jack Johnson contract as one that stands little chance of maintaining its value over the term and the same argument could be made for Patric Hornqvist as well. However, Rutherford just signed those deals and wouldn’t move them even if he could. That leaves a short list of players who could be moved and the only one that sticks out as being overpriced is Carl Hagelin. Hagelin has played an important part of the Penguins’ reign over the past few years, but at $4MM he has not cracked 40 points in any of the three seasons and can go cold for weeks at a time. Rutherford won’t make a move unless it can benefit the team, but if he can get another scoring winger in exchange for a package that dumps Hagelin’s salary, he’ll do it.

San Jose Sharks: None

Mikkel Boedker, Joel Ward, and Paul Martin are all gone. Two top forwards, the two best defensemen, and the starting goalie are all locked up long-term at a reasonable rate. The Sharks have almost $4.5MM in cap space this season, giving them room to add. Congratulations to GM Doug Wilson and his staff. This roster is the epitome of cap compliance mixed with depth and talent. There is not one contract that the team would be interested in dumping.

St. Louis Blues: Alexander Steen – three years, $17.25MM remaining

The Blues currently have all but $285K of their cap space committed to 24 players. The team may send Chris Thorburn or Jordan Nolan down to the AHL, but will only gain marginal space. Something else has to give. If they could target any player to move to alleviate some pressure, it would be Alexander Steen. With just seven forwards and three defensemen (as of now) signed beyond next season and the majority of players in line for raises or free agent replacements, these cap woes aren’t going away anytime soon and an expensive long-term deal needs to be shipped out. Understandably, St. Louis is all in this season and wouldn’t be eager to ship out an important top-six piece. However, Ryan O’Reilly, Vladimir Tarasenko, Brayden Schenn, and Jaden Schwartz are the new young core up front now and paying 34-year-old Steen $5.75MM for three more years for declining production just doesn’t make sense. The Blues could potentially land some nice pieces from another contender for Steen as well. Admittedly, the Tyler Bozak contract looks even worse than Steen’s, but the Blues won’t be looking to trade a player they just signed.

Tampa Bay Lightning: Ryan Callahan – two years, $11.6MM remaining

The long-term implications of several other deals aside, the Lightning’s Stanley Cup window is wide open and their focus is on the here and now. The one player really impeding their ability to add freely to the roster is Ryan Callahan. While GM Steve Yzerman has excelled at extending most of his core below market value, the six-year, $34.8MM contract for Callahan was a mistake. Injuries limited Callahan to just 18 games in 2016-17, but last year he played in 67 games yet he only managed to score 18 points. Callahan’s days as an impact player are over, but he is still being paid like one at $5.8MM. While Tampa Bay can manage this season with close to $3MM in cap space, they would have more to work with without him. However, Callahan’s contract will really present a major road block next summer, when the Bolts need to re-sign Brayden Point, Yanni Gourde, Anton Stralman, and more. There is no doubt that Yzerman will look to unload Callahan’s contract before it comes to that point.

Toronto Maple Leafs: Nikita Zaitsev – six years, $27MM remaining

The Maple Leafs severely jumped the gun when they rewarded Nikita Zaitsev with a seven-year deal after his rookie season in 2016-17. Although Zaitsev was an import, making his NHL debut at 25 years old, his situation epitomizes why bridge deals exist. Toronto sought to lock him up long term and gave him nearly a maximum term at $4.5MM, just $500K less per year than top defender Morgan Rielly. In his encore performance last season, he showed that he is not worthy of the salary nor length of that contract, dropping from 36 points to 13 points for the year, turning the puck over at an alarming rate, and eventually becoming a healthy scratch. This team simply can’t afford the type of long-term mistake that they made with Zaitsev. While it’s nice that they have Reilly, John Tavares, and Nazem Kadri signed long-term, it’s Auston Matthews, Mitch Marner, and William Nylander they need to worry about. The Maple Leafs will have to balance multiple expensive, long-term deals moving forward and would love for Zaitsev’s to not be one of them.

Vancouver Canucks: Loui Eriksson – four years, $24MM remaining

It seems unlikely that the recently-signed deals for Jay Beagle and Antoine Roussel will work out well, but they at least deserve some time. Loui Eriksson has had his time and has done nothing with it. While the Canucks aren’t under any cap pressure, they can’t enjoy seeing Eriksson’s $6MM cap hit – the highest on the team – on the books for four more years, especially when the bulk of his front-loaded salary has already been paid out. Eriksson was brought in with an expectation that he would be the ultimate fit with Daniel and Henrik Sedin. Instead, he has scored just 47 points combined over two seasons, less than his final season total with the Boston Bruins. The Sedins are now gone, the team is trying to get both younger and more physical and defensive-minded, and Eriksson is simply an expensive poor fit. There’s not much more to say about a player who desperately needs a change of scenery and a team that wants him gone.

Vegas Golden Knights: None

The Golden Knights are riding high after an outrageously successful first season in the NHL. It is highly unlikely that they see anything wrong with their current contracts, almost all of which were either hand-picked or signed by GM George McPhee. Give it some time and that could change. Reilly Smith is notorious for a significant drop in production in his second year with a team, but is signed for four more years at $5MM. Paul Stastny for three years at $6.5MM per seems like a solid deal, but he has always produced better surrounded by equal talent. Does Vegas have enough to justify his signing? A $2.775MM cap hit for Ryan Reaves doesn’t seem to make a whole lot of sense. Finally, there’s the three-year, $21MM extension for heroic goalie but also 33-year-old well-worn vet Marc-Andre Fleury, which could end poorly. And this isn’t even counting what could be a massive reactionary contract for one-year breakout star William Karlsson. The Knights don’t see any problems right now after finding immediate success, but if they slide significantly in year two, things could get ugly.

Washington Capitals: T.J. Oshie – seven years, $40.25MM remaining

No, it’s not Tom Wilson. The call of the question is which contract each team wants to trade, not which is objectively the worst. Wilson’s contract does seem excessive, but he is just 24 and could grow into that salary (doubtful but possible). Plus, the organization loves what he brings to the team. T.J. Oshie on the other hand is heading in the wrong direction. Oshie has done what he was brought in to do: help the Capitals win the Stanley Cup. It took a max eight-year term to keep Oshie off the market last summer and now Washington has their Cup but also has a 31-year-old with diminishing returns signed for seven more years. Oshie could absolutely still help the Capitals over the next few years, but it’s doubtful that he will be back in 60-point range in that time. He also will be nothing more than a cap space vacuum when he’s in his late thirties making $5.75MM. Oshie is a great player and one of the more likeable guys in the league, but this contract has little upside left. The Capitals would at the very least consider trading Oshie now, which can’t be said for most of their other core players.

Winnipeg Jets: Jacob Trouba – one year, $5.5MM remaining

The list ends with a tricky one. Is $5.5MM a fair value for Trouba? An arbitrator thinks so and the Jets would likely agree. However, Trouba’s contract has been a nightmare for the team. The young defenseman clearly does not want to be in Winnipeg and has set himself up for yet another arbitration clash next summer, after which he will bolt in free agency. The Jets have no long-term security with Trouba and that meddles with their future planning. With Blake Wheeler, Tyler Myers, and several others also in need of new contracts next summer, the Jets don’t need another Trouba arbitration award cutting into their cap space just so that he can walk after the season. The team will definitely look to get maximum value in a trade for Trouba over the next season.