Two months ago I put together a series of thoughts on the state of the Ottawa Senators and the organization’s financial distress. Point number two was dedicated to Erik Karlsson.

I encourage you to read the entire linked post, but I’ll quickly paraphrase each subsection. a) We were seeing only the beginning of Erik Karlsson vs. the Ottawa Senators; b) The justification underpinning the ‘Erik Karlsson had to submit a no-trade list’ was junk based on the timeline provided; and c) The primary driver behind the strained relationship was specific to ownership, and not the front office.

The trade discussion encircling Karlsson and Ottawa is now inescapable. Ask ten people about the feasibility about a trade and you’ll surely get ten different responses. The one thing I wanted to do though is spend some time talking about the things I have heard over the past half-season and, more generally, providing an eleventh thought – based on what I know – about a potential trade.

So, let’s begin.

1a.) All of the organizational in-fighting really comes down to two people: the owner, and the player. There are three things professional athletes want – long-term security, a lot of money, and a chance to win championships. Ottawa has always had the upper hand on the first point. Karlsson clearly loves living in the city. That means quite a bit. Historically, be it the NHL or any other major league, it becomes increasingly difficult to pry a player out of his ‘home base’ as he develops more and more comfort with his environment. It’s no different than any employee of any organization, really.

But the other two areas are huge going concerns. Not to beat the deadest of dead horses into the ground but Ottawa’s financial situation is grim. The team wasn’t financially stable when they were winning a ton last year. One can only wonder what it looks like now, with continually sliding attendance and a team that couldn’t string together a series of wins at any point during the season. The team has few remaining executives. Some have ‘left’ the company. Some have been fired. Some have been fired and turned around to sue the team. The owner is now juggling multiple executive hats. It’s created incredible uncertainty within the organization, and that’s permeated into the locker room.

Can this team – a team in a full-blown rebuild with a [still recovering?] superstar player looking for a max contract – genuinely afford an $80mm contract, a contract which will likely carry heaps of signing bonus money and some front-loading? It just seems increasingly unlikely. And if the team is dedicated to a true rebuild plan as reported, does the Karlsson retention even make hockey sense? It’s a valid question.

1b.) I cannot emphasize this point enough, and I’m sure I have written it a half-dozen times or so now: do not discount the impact that Daniel Alfredsson leaving the organization had. Or the impact it had when he left the organization for a second time. Or the discussion surrounding Kyle Turris’ exit from the team. Or any of the unhinged rants about financial investment into hockey operations. It’s created two perceptions, fair or not. The first is that the team is selectively loyal. (As an aside, I think all teams and all players should be selectively loyal. But these are the issues you can run into when two or more parties aren’t aligned.) The second is that the team is not serious about winning a championship, or has no plan to win a championship, or both.



1c.) General managers can pick up a phone and call Pierre Dorion and talk about a trade. Players can pick up a phone and call Erik Karlsson and talk about what it’s like to play for an organization. The latter is true regardless of whether a trade materializes today or if he leaves the organization when his contract expires. This is, to be absolutely clear, happening.



2a.) The discussion around whether or not Erik Karlsson will be moved at the trade deadline is interesting, but ultimately immaterial. It’s true that increasing the market is probably in Ottawa’s best interest and that would mean a summer trade where teams aren’t already hitting their heads on the cap ceiling. But there’s also an incentive for true contenders to make a swing at Karlsson right now. As one example, it’s almost certainly in Tampa Bay’s interest to make a deal today. They’ll get two shots at a Stanley Cup with Karlsson on a super team-friendly contract versus one. And they have enough cap room to make a trade work, though reports about Ottawa’s desire to include Bobby Ryan’s contract into this deal make it awfully difficult.



2b.) If you needed any further indication that this move is about clearing money above all else, the Bobby Ryan attachment would help solidify it. Karlsson, on his deal and in his condition, is one of the most valuable trade pieces a team can possibly have. Even entertaining the idea of utilizing his value to get off of yet another bad contract should tell you all you need to know. And, again, a Ryan inclusion makes this deal infinitely more difficult from a trade deadline perspective. A team taking on roughly $14mm in cap just doesn’t happen in March – not unless it’s a mega-trade of truly epic proportions.



3.) The organization can’t technically negotiate with players until a certain interval pre-dating their contract extension is reached, but that doesn’t stop groups from having, uh, informal discussions. It’s one of the big reasons why you see a slew of contract extensions on the same day in the summer (the NBA, which has a similar CBA in this light, has a ridiculous rash every single summer). Teams and players generally know the landing spot for a deal and when they are able to execute on it, they sign the dotted line and move on. Not that Ottawa needed any reinforcement but it seems reasonably likely to me that they are aware that Karlsson’s not stepping down on his contract demands any time soon. As I noted earlier, even if he’s paid marginal top-out on an 8-year deal, that’s at least $80MM in liabilities to a single player. This is the part that I think Karlsson, right or wrong, will have to wear. His commentary about wanting to be paid top dollar has had a chilling effect on negotiations before they could even begin. And it’s one of the reasons behind Ottawa “aggressively listening” to Karlsson trade proposals.



4a.) I don’t think Erik Karlsson wants out of Ottawa. I do think he wants out of the Ottawa Senators organization. He is, to quote multiple sources close to the situation, “unhappy”.



4b.) There are two ways Ottawa can retain Erik Karlsson. The first is an ownership change. (One including Daniel Alfredsson would surely be a plus.) The second is rebuilding a bridge that’s been so thoroughly burned you can see the smoke from Sweden. I’m skeptical that this can occur but if Pierre Dorion is genuine about his desire to retain Karlsson, he needs to first play the role of middleman or mediator, then convince his cornerstone player that the team has a real plan in place to succeed long-term … then give him at least $80mm.



5.) My opinion, and my opinion only: I just don’t see how Erik Karlsson is in an Ottawa Senators sweater come October 1. Maybe it’s a deadline deal. Maybe it’s a summer deal. But I’m reasonably convinced we have reached a point of no return and although a lot of people will point to a disappointing 2017-18 season as the genesis, the reality is the relationship has soured over years of increasing distrust and skepticism on trust and organizational direction.