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Draft Guide

Top 25 Transactions

by Ryan Dadoun
Updated On: October 4, 2018, 4:09 pm ET

Ultimately, when it comes to preseason predictions, some are going to agree with your assessments and others won’t.  Even in that environment though, attempting to assemble a list of the Top 25 transactions is particularly divisive because people can’t even agree on the definition of a good transaction. 


For example, Chicago has re-signed Patrick Kane and Jonathan Toews to matching eight-year, $84 million contracts.  Kane and Toews are amazing players that have defined that franchise, so keeping them on board was naturally a must, but at the same time, those cap hits are, at best, fair value. 


That matters because in a hard cap, the Stanley Cup winner is ultimately the team that got the most value out of what they had.  Chicago had an edge because Kane/Toews were undervalued at $6.3 million and that edge will evaporate when those contracts take effect.  Just as Pittsburgh had an edge in 2009 when they won the Cup because Evgeni Malkin was still on an entry-level contract.  Ever since the Penguins have had to pay fair value for Crosby/Malkin, they haven’t made in to the finals.  They’ve had depth problems because paying a pair of superstars what they’re worth eats up a significant portion of the cap. 


Now this isn’t an argument against Chicago or Pittsburgh or an attempt to say that Chicago was wrong for re-signing Kane/Toews.  Taking a step back from cap theory for a second, from a practical standpoint, Chicago really had no chose.  The duo revitalized their franchise and it would have been a PR nightmare to trade one or both of them or, worse, let either one walk.  It would have been interpreted by the masses that the Blackhawks’ ownership had gotten cheap. 


Instead, this is being brought up to highlight that there are different ways of interpreting what makes a good transaction.  For the purposes of this list, I’m going to attempt to blend value based on the cap hit/length of the deal with the talent of the player.  After all, if you are too disciplined in the interest of never overpaying a player than you might end up with plenty of cap space, but little talent.  As you’ll see, noteworthy trades have also been included in this list and in those cases, what was given up will also be a factor. 


One final note is that the Kane/Toews extension won’t be on this list, not because they aren’t good enough, but because they won’t impact the 2014-15 campaign, given that they don’t start until 2015-16. 


1) Dallas acquires Jason Spezza and Ludwig Karlsson from the Ottawa Senators in exchange for Alex Chiasson, Alexander Guptill, Nicholas Paul, and a 2015 second round pick 


While it might sound like the Stars gave up a lot for Spezza just due to the number of moving pieces involved, the prospects the Stars surrendered aren’t top-end players and Chiasson doesn’t have star potential.  This is really a case of Stars GM Jim Nill taking advantage of the fact that Ottawa’s hands were tied because Spezza both demanded a trade and limited the number of teams he would accept a deal to. 



With the free agent market being relatively weak, an argument can be made that by acquiring Spezza, the Stars made got the biggest upgrade of the summer.  With Spezza working for them, the Stars are great up the middle and are in a position to put forward two strong scoring lines. 


2) Marian Gaborik signs a seven-year, $34.3 million contract extension with Los Angeles 


The Kings managed to win the Stanley Cup for the second time in three years, but that probably wouldn’t have happened if they didn’t acquire Gaborik from Columbus in March.  Gaborik was the missing piece the Kings needed to spark their anemic offense and losing him as an unrestricted free agent would have been a big blow. 


That being said, Los Angeles didn’t have a lot of cap space to work with, so they were fortunate that Gaborik was willing to sign a cap friendly contract in exchange for a longer term and the luxury of playing for a contender.  The Kings are still taking a risk given Gaborik’s injury history, but for a $4.9 million annual cap hit, it’s a risk well worth taking. 


3) Brad Richards signs a one-year, $2 million contract with Chicago 


Los Angeles wasn’t the only team that managed to lure a big name player to take a substantial discount for the sake of playing for a contender.  Chicago needed a second-line center, but didn’t have the cap space to easily get a guy like Jason Spezza or Ryan Kesler.  Fortunately they didn’t have to as Richards was willing to take a substantial pay cut in order to join one of the best franchises in the NHL. 


You could argue that Richards could afford to do so because he was bought out by the Rangers, but that misses the point.  The NHL is full of rich players and most don’t start taking big pay cuts just because they’ve already made millions.  Sure, Richards is already getting paid by the Rangers, but he could have still decided to maximize his paycheck by signing with a team that could have afforded his market value and he chose not to. 


4) Thomas Vanek signs a three-year, $19.5 million contract with Minnesota 


Vanek’s cap hit seems about right, but what makes this deal great is the term.  The Wild didn’t want to lock themselves in with Vanek long-term because they want to make sure they have cap space available for when their promising young players are due for their big paydays.  On top of that, had they signed Vanek to a long-term deal, it would have been far riskier as Vanek is already 30 (31 in January).  This way they get his prime years without committing to keeping him during his decline. 


You could argue that Vanek’s market value went down after his rough playoff run, but we would counter that years of success outweigh a rough month.  If his market value truly went down, then Minnesota deserves recognition for taking advantage of the situation. 


5) Nashville acquires James Neal from the Pittsburgh Penguins in exchange for Nick Spaling and Patric Hornqvist 


The Predators went into the summer with the objective of upgrading their offense and they took a significant step in that direction when they got Neal.  The former 40-goal scorer is locked up for four more years at $5 million per, so this might prove to be a bit of a steal for them. 


That being said, there’s a couple reasons why this didn’t rank higher.  One is that Neal is a risk to regress now that he’s away from Pittsburgh and the likes of Sidney Crosby and his regular center, Evgeni Malkin.  The other is that Neal has dealt with a series of injuries over the last couple of years and has displayed a lack of discipline that’s got him into some trouble.  So while Neal might be able to lead the Predators’ charge for years to come, he’s not a safe bet. 


6) Christian Ehrhoff signs a one-year, $4 million contract with Pittsburgh 


The Pittsburgh Penguins didn’t have the cap space to re-sign Matt Niskanen, but they were able to replace him in the short-term with the Ehrhoff signing.  Ehrhoff had six goals and 33 points in 79 contests last season, which might not sound particularly special, but keep in mind he was playing on a Sabres’ squad that averaged just 1.83 goals per game. 


Moving from one of the worst offensive teams in the league to one of the best should do wonders for Ehrhoff’s production and that’s likely why he was willing to sign a relatively cheap one-year deal with the Penguins.  He’ll cash in next summer if all goes well, but for now the Penguins will reap the rewards. 


7) Anaheim acquires Ryan Kesler and a 2015 third round pick from the Vancouver Canucks in exchange for Nick BoninoLuca Sbisa, the 24th overall pick in the 2014 draft (Jared McCann), and the 85th overall pick in the 2014 draft (Keegan Iverson) 


Like Dallas did with Ottawa, Anaheim was able to take advantage of the fact that Vancouver’s options were limited because Kesler was demanding a trade.  Kesler will serve in a similar capacity as Spezza in the sense that both will be the second-line centers on their new teams, although Kesler brings a little less skill and more grit to the role. 


The Ducks are getting Kesler for longer as well as his six-year, $30 million deal runs through the 2015-16 campaign.  The single biggest reason this trade slipped below the Spezza deal is because the Ducks gave up more, including a potentially decent second-line center, a defenseman with a fair amount of upside, and a first rounder. 


8) Paul Stastny signs a four-year, $28 million contract with St. Louis 


Stastny’s $7 million annual cap hit is perhaps a bit high given that he’s recorded between 50-60 points in each of his last three 82-game campaigns, but the fact that the 28-year-old agreed to just a four-year deal gives St. Louis some flexibility. 


More than that though, this is an example of why judging a team’s free agent success based on the player’s talent to cap hit ratio would give us an incomplete picture.  Are the Blues giving Stastny more than his market value (compared to what other $7 million players bring to the table)?  Perhaps, but he was one of the best free agents out there and if the alternative was simply keeping the cap space free, then that wouldn’t have helped the Blues.  They’re in a win-now mode and under those circumstances, they should be spending to the cap.  If this is what they had to give to lure a top-line center to St. Louis, then so be it. 


9) Arizona acquires B.J. Crombeen and Sam Gagner from Tampa Bay in exchange for a 2015 sixth round draft pick 


In other words, the Tampa Bay Lightning were looking to dump those contracts to free up some cap space and Arizona had the space to spare.  In Crombeen, the Coyotes are getting an enforcer who could play on their fourth line, but it’s the addition of Gagner that makes this trade interesting. 


Gagner is coming off of a rough season where he recorded just 37 points in 67 games, but he got off on the wrong foot because he missed the start of the season with a broken jaw.  After the humbling terms of this trade – the second time he was moved this summer – he’s motivated to bounce back this season.  He might emerge as one of the Coyotes’ top forwards, which admittedly isn’t saying much given their roster, but is still pretty nice for the price of a sixth rounder. 


10) Mike Ribeiro signs a one-year, $1.05 million contract with Nashville 


After the Predators signed James Neal, the next step of their offseason project was finding a center worthy of playing with him.  They couldn’t land any of the big names on the free agent or trade market, but they did get one of the summer’s better bargains in Ribeiro. 


That being said, there’s a reason why he came so cheap.  He only recorded 47 points in 80 contests last season and was bought out by the Coyotes due to “behavioral issues.”  That’s an awfully big red flag, although Ribeiro later said he had marital problems that he’s working through.  All that considered, for the amount he’s making, he’s well worth the risk as he can be a 70 or so point player under the best of circumstances. 


11) Jaroslav Halak signs a four-year, $18 million contract with the New York Islanders 


The St. Louis Blues dealt Halak a pretty big insult in February when they traded him away just before the playoffs in favor of Ryan Miller.  Halak had been great in St. Louis, but injuries had prevented him from participating in their playoff runs – with the exception of 104 minutes in 2012.  Consequently his last real playoff run was in 2010 when he was instrumental in carrying the Montreal Canadiens to the Eastern Conference Final. 


Montreal rewarded him for his efforts by trading him away that summer because they wanted to commit to Carey Price.  At this point Halak has to be developing a complex.  At any rate, he’s one of the better and arguably more underrated starters in the league and the fact that the Islanders could get him for a cap hit of $4.5 million annually is a pretty big win for them. 


12) Steve Downie signs a one-year, $1 million contract with Pittsburgh 


Downie dealt with balance and hearing problems last season and had to undergo multiple ear surgeries to correct the problem, but he should be fine for the start of training camp.  He was also limited to just two games in 2013, which is probably contributed to the Penguins getting him so cheap. 


He’s known for his controversial play, but he’s not a pure enforcer.  Downie has some skill and could actually accumulate a fair number of points if he gets some playing time with Sidney Crosby or Evgeni Malkin.  As a player was was hired to protect the Penguins’ big two, $1 million is a fair price, but given that he’s also a capable top-nine forward even without that aspect of his game, he looks like a steal. 


13) Marek Zidlicky signs a one-year, $4 million contract with New Jersey. 


Zidlicky turned 37 in February, so he wasn’t in line for a blockbuster contract, but he still had an opportunity to cash in on his 42-point 2013-14 campaign.  It certainly wouldn’t have been surprising if he got a contract comparable to Dan Boyle’s two-year, $9 million deal. 


Instead Zidlicky decided to stick with the Devils, which is fortunate for them because it’s not like they played well enough last season to warrant players giving them a hometown discount.  Even at his age, Zidlicky reasonably could have another 40-point season in him, which makes his price tag look pretty good. 


14) Ryan Miller signs a three-year, $18 million contract with Vancouver 


As we touched on briefly with Halak, the St. Louis Blues acquired Miller because they thought he was better qualified to help them win the Stanley Cup.  It didn’t work out like that and after a poor showing in the playoffs, the Blues made it clear that they had no intention of re-signing Miller even after trading a considerable amount to get him. 


Miller is still a great goaltender though and while his $6 million cap hit is merely fair, the three-year term works well for Vancouver.  More than that though, this signing makes all of the Canucks’ other previously questionable goaltending deals look justifiable.  After all, they traded both Cory Schneider and Roberto Luongo for assets, but by signing Miller, their goaltending situation still looks strong. 


15) Matt Niskanen signs a seven-year, $40.25 million contract with Washington 


Niskanen’s deal isn’t a steal by any stretch of the imagination.  You could argue that his $5.75 million cap hit actually isn’t that bad, but he’s still a gamble.  After all, Washington is making a seven-year commitment to an offensive defenseman who has only surpass the 30-point mark twice in his seven-year career. 


All the same, the way the market for defenseman is, it’s highly unlikely that a talented one in his prime is going to come cheap.  The risk associated with this signing is why it slipped all the way to 15th place, but there’s no question that Washington got better by signing him. 


16) Matt Moulson signs a five-year, $25 million contract with Buffalo 


The best kind of free agent signing is one that involves a player you’ve dealt away as a rental coming back.  The Wild gave Moulson along with Cody McCormick to the Minnesota Wild in exchange for Torrey Mitchell and a pair of second round picks. 


Putting that aside, a $5 million annual cap hit seems awfully fair in this market for a forward that can give you around 60 points per season.  He can play on the Sabres’ top line and should help mentor the Sabres’ young forwards as the team moves forward in its rebuild. 


17) Kimmo Timonen signs a one-year, $2 million contract/Michael Del Zotto signs a $1.3 million one-year deal with Philadelphia 


Timonen got off to a rough start last season, but he bounced back to finish with 35 points in 77 games.  Unfortunately after he signed a very friendly one year contract for only $2 million,  he was diagnosed with blood clots in his lower right leg and both lungs and could miss the entire season. The Flyers were forced into another move and signed free agent defenseman Michael Del Zotto to a cap-friendly one year deal. Del Zotto has a lot to prove, since his last good season was in 2011-12 when he had 10 goals and 41 points in 77 games as a 21-year-old. He just turned 24 so he has plenty of time to turn his career around but has only six goals and 31 assists in 107 games since then while being a healthy scratch on numerous occasions. 


18) Olli Jokinen signs a one-year, $2.5 million contract with Nashville 


As mentioned above, the Predators couldn’t lure a top free agent to Nashville, so they went bargain bin shopping instead.  Jokinen is less of a roll of the dice than some of the other guys they brought in.  He doesn’t have the upside of Ribeiro, but Jokinen’s a safe bet to get 40-50 points.  He wouldn’t look out of place on Nashville’s second line and there aren’t too many veterans at that price point you can say that about. 


19) Columbus acquires Scott Hartnell from Philadelphia in exchange for R.J. Umberger and a 2015 fourth round pick 


The Blue Jackets needed to unload Umberger after he fell out of favor with the team last season and getting Hartnell in the process was great for them.  Hartnell should fit in well in Columbus as he’s another forward who brings a blend of skill and grit to the table.  The Blue Jackets are building a team that other clubs will dread playing. 


This trade isn’t ranked higher out of respect for what Umberger can do.  He might not have fit into Columbus’ plans anymore, but he’s still a capable top-six forward and should benefit from the fresh start. 


20) Steve Ott signs a two-year, $5.2 million contract with St. Louis 


Ott is primarily an enforcer, but he can do just enough with the puck to validate using him as a top-six forward.  On top of that, he’s capable of serving as a leader.  The Blues didn’t give him a ton of playing time during his 23-game stint with them in 2013-14, but things might be a bit different now that Vladimir Sobotka has bolted to the KHL. 


As a physical third liner with the potential to see some time on the second line, Ott’s cap hit of $2.6 million doesn’t look bad. 


21) David Legwand signs a two-year, $6 million contract with Ottawa 


Detroit acquired Legwand as a rental in March and didn’t really fit in there, but he still finished the season with 51 points in 83 games.  He’s capable of putting up those kinds of numbers again and figures to get a fair amount of playing time in Ottawa now that Jason Spezza is gone.  He’s certainly not a remarkable center by NHL standards, but it’s a fair price for his services. 


22) Jarome Iginla signs a three-year, $16 million contract with Colorado 


This was a bit of a tough one to rank and there’s bound to be people who will feel that he should have been placed higher.  After all, a $5,333,333 annual cap hit for a player who has scored at least 30 goals in each of the last 12 82-game seasons seems pretty good. 


At the same time, he’s 37 and the Avalanche are taking a huge chance by giving him a three-year deal.  It wouldn’t be shocking if he declines next season and it’s doubtful that he’ll still be nearly as effective by 2016-17. 


23) Derek Roy signs a one-year, $1 million contract with Nashville 


Why did Roy rank below Jokinen and Ribeiro when it comes to the Predators bargain bin signings?  In Ribeiro, the Predators were getting a player who was one season removed from a point-per-game campaign and in Jokinen you got a player that’s at least a decent bet to hold his own on the second line if asked.  Roy is significantly further removed from his glory days than Ribeiro and might not even end up as a top-six forward. 


He’s only 31 years old, so it’s entirely possible that he’ll find his game and once again be a player that can provide you with 20-plus goals and over 60 points.  That’s enough to get him on this list, but he’s this low on it because we don’t consider him a good bet to do that. 


24)  Brian Elliott signs a three-year, $7.5 million contract with St. Louis 


Elliott has been a fantastic backup goaltender over the last few years in St. Louis and he’ll enter the 2014-15 campaign as a serious contender for the starting role.  If he runs with it, then his contract will look like a steal.  That being said, the 29-year-old has also endured some remarkably nasty cold streaks over the course of his career that make us nervous about the idea of him leading a team.  Even if he doesn’t work out as the team’s number one goaltender though, his cap hit is still fair for a great backup.  With that in mind, there’s not a lot to dislike about this move. 


25) Brenden Morrow signs a one-year, $1.55 million contract with Tampa Bay 


This isn’t a particularly exciting move and even with his relatively inexpensive cap hit, we don’t see Morrow as much of a bargain.  Still, he’s a great addition to a team already good enough to make the playoffs that’s looking to make some noise once they get there.  He’s not going to contribute much offensive at this point, but he plays with a physical edge that makes him worthwhile as a bottom-six forward and he brings a wealth of experience to the table. 


Steve Stamkos doesn’t have a lot of experience wearing the ‘C’ and Morrow is someone that’s been in that position that can help Stamkos adjust to his new role.

Ryan Dadoun
Ryan Dadoun is an Associate Editor for Hockey on Rotoworld. Feel free to follow him on Twitter or check out his blog.