At this point, it seems like all but a sure thing. The Ottawa Senators’ hockey-playing situation has gone from “inability to read the warning signs”, made most apparent with their defiance of odds and subsequent acquisition of star forward Matt Duchene in November, to outright disaster, with rumours rampant of confusion in the dressing room, drama in the front office, and penny-pinching efforts in the boardroom. The latter point is the biggest one; what Eugene Melnyk says is ultimately what goes, especially now that he’s named himself CEO of the team.

The dagger to this? A potentially bitter breakup with their franchise player. Anyone paying attention to the hockey world right now is well aware that Erik Karlsson is, at the very least, in the “listening to offers” stage of being moved. The 27-year-old, who has about a year and a half remaining on his seven-year contract, has immediately catapulted into the top of the charts as far as Trade Deadline speculation, and that’s in no way surprising.

After all, we’re talking about a defenceman who, before hitting free agency for the first time in his career, has already won two Norris Trophies, and if it wasn’t for a combination of people treating the award like something that needed to be shared and an ongoing fundamental debate about what defines a great defenceman, he’d probably have won of the award in 5 of the last 6 years (with one year skipped because of Matt Cooke).

There is little to no doubt that Karlsson is the best defenceman of our generation, by a significant margin. As the game evolves towards a high-pace, mobility-oriented, possession-oriented game, Karlsson stands alone. Despite playing on some incredibly mediocre to rough Senators rosters, Karlsson has averaged a 74-point scoring pace over the past seven seasons, and Ottawa’s share of shot attempts has been over 5% better with him on the ice than without him, the highest in the NHL in that stretch. There is a very good argument that he is, with over a decade to go in his career, already the best right-handed defenceman to ever play the game, given how weak the position was until recent years and given the fact that he is well ahead of anyone else in era-adjusted points per game. While offensive numbers aren’t everything, combine them with his known ability to drive differential, and the quality of player becomes apparent here.

With all of this in mind, the idea of trading a player doesn’t make sense, but also does. If the Senators don’t expect to be good again until his early-mid 30’s, and he is most valuable to other teams now while his contract is still on the lower side, than this is the ultimate sell-high moment. While Ottawa have a few noteworthy prospects, their total pool is one of the emptiest in the league at the moment. Their hopes of turning the current group into a competitive team are slim. Getting as many draft picks and prospects as you can, with maybe a roster player or two that can be re-flipped later, would be the absolute most optimal move to get the team back on the right track for the long haul.

But here’s the thing: That $6.5 million cap hit is what makes this such a swingable scenario for other teams. In a league where depth defencemen who are good in the locker room are upwards of $4 million, and number ones who aren’t in Karlsson’s league are pushing nine or ten, he provides tremendous value to a contending team who needs one more superstar to separate themselves from the pack. You know what nerfs that value? Expecting the other team to take on substantial salary with him.

Which, of course, is exactly what the Senators are attempting to do:

The Senators have let it be known that the number of notable pieces in the price could be discounted somewhat if Ryan and his contract are taken on as part of any Karlsson deal. The oft-injured, soon-to-be 31-year-old, who has never scored for Ottawa the way he did for Anaheim, has another four years on a contract that pays him $7.5 million per season with an annual cap hit of $7.25 million.

The Senators know full well that the “Ryan provision” could severely limit the number of Karlsson contenders; that some teams simply aren’t in a position to take on Ryan’s salary or cap hit at the deadline, even if the plan would be to buy out Ryan in the off-season.

Bobby Ryan’s contract, for all intents and purposes, is one of the worst in the NHL. The 30-year-old has a modified No Trade / No Movement Clause, barring him from being traded to 10 teams of his choice, and barring him from being sent down to the AHL. To make matters worse, he still has four and a half years remaining on it, with a cap hit of $7.25 million. He is one of the 25 highest paid forwards in the National Hockey League, which is incredibly impressive when you consider that his last 60-point season was seven years ago, his last 25-goal season was six years ago, and that his 43 point pace this year could be considered a massive bounce-back.

No contending team is going to want to pay $7.25 million for a player that maxes out as playing on their third line. It’s simply out of the question unless you believe this is absolutely the last year your window and that you’ll be selling again in a few months, which makes giving the world for Karlsson seem counter-intuitive. For what it’s worth, here are the teams that could afford to acquire both players at their full price of $13.75 million right now, using pro-rated space:

Nashville ($13.8), Anaheim ($15.1), San Jose ($20.3), Columbus ($21.1), Buffalo ($24.1), Winnipeg ($25.1), Florida ($29.9), Montreal ($30.4), New Jersey ($31.8), Las Vegas ($33.7), Edmonton ($34.6), Colorado ($35.1), Carolina ($68.3), and Arizona ($71.6).

Let’s shed this list a bit. Arizona is a budget team that is way out of the playoff picture, so they’re probably out. Carolina would be interesting, capable of giving up a bunch of young forwards, and could be-fill their Erik Karlsson quota, but defence is the least of that team’s worries. That last point also applies to Nashville and Anaheim. Edmonton would be a fun fit if management had a plan for shedding the Milan Lucic and Kris Russell contracts, but that level of foresight is unlikely from them. Montreal is about to sell, San Jose already has Brent Bruns, and Florida’s in a bit of a real-dollar crunch themselves.

This leaves us with Columbus, Buffalo, Winnipeg, New Jersey, and Vegas. Buffalo would be an awesome fit if they combined a deal with some well-placed offseason signings, but I feel like management would have trouble selling the fanbase on a “buy” move; especially if Ottawa asks for their first. Vegas might want to go for it in their first year, but any move that involves them selling futures is a gigantic risk, considering how little they have to work with right now. Winnipeg has Nikolaj Ehlers’ raise kicking in next year, and extensions for a vast chunk of their core coming either this year or next, making Ryan a hard attachment for them to take. New Jersey is only one year into their “rise” and might want to see what they have first. Columbus is likely the best all-around fit out of teams who have the space to take on both deals, but even in their case, they have just eight players signed beyond the end of next year.

With all of that in mind, I could still see these teams being interested in making a deal because, well, it’s Erik Karlsson at stake, but the Ryan attachment makes it enough of a risk to their long-term plans that they won’t be desperate to win the bidding war, leading to a significantly lower price. Without that attachment, though? That makes things a lot easier and manageable for them, and also immediately allows the Kings, Lightning, Flames, Flyers, and maaaaybe the Leafs and Islanders to get into the mix. It’s a significant additional playing field and gives teams much more incentive to give up assets. As it stands, Ryan’s contract is so above market value that even a 50% retention would make him an excessive asset; the grenade of taking him clean likely pulls at least a 1st round pick or top prospect out of any Karlsson deal.

“But Eugene’s money!” is the common response here. Even the casual fan of an opposing team knows that Melnyk is looking to cost cut in just about any way possible, even threatening to look at different cities to play in if there’s a better financial situation. With that in mind, I’m sure that he would prefer that his hockey team not be paying another $37 million to someone to not put additional fans in the stands, nor help make the team into a contender.

But that’s not the way to look at it.

Firstly, Ryan’s contract isn’t a particularly terrible real dollar situation; while he’s not exactly a front-loaded player who gets cheaper over time, something budget teams tend to put on a pedestal, his real dollars owed for the remainder of his term only exceed his cap hit by $1 million, and his annual signing bonus only accounts for about a quarter of his cap hit. As far as bad deals go, this one is more deadweight to the framework of the hockey club than it is to the business.

Secondly, the cap floor exists. Melnyk can look to cut costs all he wants, but at the end of the day, he needs his team to get to 85% of the ceiling if he wants them to play hockey games. Right now, that’s $55.4 million but could get to $60 million by next season if revenue goals go just right. After the trade of Derrick Brassard to Pittsburgh (which happened while I was writing this post), the Sens are now in a position where they’re committed to $56.8 million in salary for next year, with Mark Stone being the only significant player left to re-sign. If they moved Karlsson on his own and didn’t have to take anything back, the Senators would be at $50.3 million.

That’s if they did nothing else. But what if they continued to sell, and instead of trying to dump Ryan’s negative-value contract, looked to move players who have plateaued by the time they’re close to competitive again? Mike Hoffman is great, but is probably at peak value now as a 28-year-old, and will probably walk as a UFA before the Senators are back in the playoff picture. Zach Smith will be 32 when his current contract expires in three years, Jean-Gabriel Pageau will be 27 in two; young enough to keep, but not substantial enough of a player to hold onto if you’re looking to reshape the organization. If a team still thinks Cody Ceci is good, it’s probably more sensible to trade him now than re-up him into his mid-late 20’s.

Craig Anderson may be hard to move because of his age (and is probably good to keep in the room), but Mike Condon likely can likely get an asset back, given that other teams were interested in signing him in the summer. If you were really aggressive about righting the ship, you could also swallow your pride and look at putting Duchene right back on the trade block that you got him from a few months prior.

That’s a lot of money that can be moved, and moved for positive assets. So much so, that even a few of those moves would put you in floor danger, which is all the more reason to hold onto a substantial contract like Ryan’s. While he holds less than zero value to another team, his value to the Senators is that he allows for them to complete the fire sale while taking up 13% of the cap room needed to reach the floor. On top of this, the young asset or assets (via picks or direct prospects) that likely remain in the Karlsson trade if the other team doesn’t have to take Ryan on will be cost-controlled for at least their first two contracts, which should benefit Ottawa financially as well.

With all of this in mind, the only way that it makes sense, be it through hockey or through money, for the Senators to attach Bobby Ryan to an Erik Karlsson trade is if they have a specific issue with Ryan and this is the only way they can move him. Through all the rampant speculation that has gone on involving the Senators, we haven’t heard anything that indicates that, so I doubt that to be the case. Attaching him as an anchor probably doesn’t give the team any actual financial gain compared to selling other players, and definitely makes the team less likely to be competitive in the long run. If I’m in Ottawa’s position, whether I’m Pierre Dorion or Eugene Melnyk, I’m selling Karlsson separately, some of the support core separately, and letting Ryan save me from the floor. Besides, every year paid off makes him more likely to return to a positive value; especially if, by some fluke (or intensive minute-gaming in a tank year), he ends up having a bounce-back season along the way.

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