On July 1, 2018, we announced that the Toronto Maple Leafs were signing John Tavares. For a young and upcoming team that had multiple superstar-level talents already on it, this was essentially the icing on the cake — and a bomb of a statement to the rest of the league — that meant the Leafs would be Cup contenders for years to come.

While the team was very good last season, ultimately it was a season filled with ups and downs that ended with a first-round loss to an excellent Boston Bruins team. It wasn’t a failure of a season, but since signing Tavares, things have not exactly gone smoothly for a team that should be in the middle of a Cup window.

As their 2018-19 season progressed, it began to be overshadowed by a contract dispute between Leafs management and William Nylander. Eventually, Nylander did return, but having missed the first few months, he was nowhere near his prime form. A .75 points per game player over the previous two seasons, Nylander produced at a .5 points per game clip while bouncing between the top three lines as he never truly found his footing and form we are accustomed to with the now 23-year-old.

After the season ended, Nylander openly acknowledged regretting the way the season unfolded. Ultimately, I am betting he will bounce back and have a fine season (and career) ahead of him, but it was something the Leafs could ill-afford to have happen as they needed peak-Nylander to go along with the rest of their team in order to go deep in the playoffs. Contrary to some beliefs out there, they were not going to go far in spite of him, and they didn’t.

This summer, the Leafs added a sorely-needed defenseman, and while (I think) they still need one more solid piece on the back end, the Morgan Rielly – Jake Muzzin – Tyson Barrie trio is clearly the best the organization has had since Bryan McCabe – Thomas Kaberle – Brian Leetch for a magical quarter of a season (although I have some additional long-term concerns on the trade to bring in Barrie below). Coupled with an attempt to add in more depth (more on that below as well), this team is stacked and should be ready for a Cup run.

And yet, there is another holdout to contend with in Mitch Marner. Again, the team will likely not go far without a high-flying Mitch Marner. They almost certainly need him and everything he brings in order to make a serious run, and who knows how he would respond to potentially missing training camp and possibly the start of the season?

The Leafs aren’t the only team facing this problem. The list of unsigned RFAs is eye-popping: Patrick Laine, Brayden Point, Mikko Rantanen, Matthew Tkachuk, to name a few. Ultimately, Kyle Dubas and the organization are caught in a tough negotiating spot that I am guessing will serve as a point of contention in the next CBA.

This is the only time young stars really have leverage. Once they are arbitration-eligible, they will be sawed off in what they are asking for. By holding out now, the pressure shifts onto the organization to pay up and the player can sit out, making the lives of managers miserable (as we have seen in Toronto). This is, in part, why I think the Leafs signed Auston Matthews to the contract they did when they did — to avoid this headache (although I believe the contract is still too short and walks him too easily to free agency).

Maybe the Leafs sign Marner before the season and this is all moot, but we don’t seem to be heading that way and Marner’s agent has a history of overseeing client holdouts. Let’s not lose sight of the forest for the trees here: When the Leafs should be in the middle of preparing for deep Cup runs, they are being held back by contract holdouts when their time should really be focused on making the final tweaks to this roster. Frustration is clearly growing within the organization – to the point where they’d rather have this end sooner than later, one way or another.

You could argue the team might be better served to trade Marner to find that missing piece on the backend while possibly adding another depth forward piece in a package trade. A trade seems unlikely and difficult, though, unless some team is dying to overpay Marner at over $11 million per year (and make no mistake, that is an overpay; he’s not the best winger in the league and should not be paid as if he is or will be one day). And that leads us to the current holdout scenario.

Complicating matters down the line, somewhat, is that Tyson Barrie and Jake Muzzin are both pending unrestricted free agents. Two quality defensemen both making under $5 million, they will each be in line for raises. If Barrie has a big season production-wise, he could be looking at a deal over $7 million per season without blinking. Barrie is reportedly already eyeing around $8 million. It will be tough to retain both, and it is difficult to see the defense improving if they lose at least one if they each keep playing to their standards.

Frederik Andersen, meanwhile, is two years away from being an unrestricted free agent with no obvious heir apparent in the organization. There seems to be the window right now for clear Cup contention and one the Leafs should be trying to maximize. To this point, they have been stuck in restricted free agent negotiations with no clear out and it is impacting the play of their top players (either directly or indirectly impacting teammates due to their absence).

Cup windows are short in the cap world. While the Leafs have a collection of talented young players, you never know for how long the window will really be open. Look at Pittsburgh throughout the Crosby era, which has not always been smooth sailing. Chicago has missed the playoffs for a few seasons now with prime Patrick Kane and Jonathan Toews years. Winnipeg already looks much worse without ever going all the way, while Nashville hasn’t been able to recapture the magic of their one Cup Finals run. This is a really difficult league to win in just once, let alone consistently.

Here’s hoping to a resolution one way or another soon so that the team can focus on maximizing their Cup window, not simply getting their current talent under contract.

Random Thoughts

– The breakdown of non-neutral zone faceoff starts last year for the Leafs’ top four centers:

PlayerOffensive ZoneDefensive Zone
Auston Matthews65.5%34.5
John Tavares58.6%41.4%
Nazem Kadri62.8%37.2%
Frederik Gauthier26.473.6%

Zone starts are not a catch-all for defensive responsibilities, but they are a snapshot into the Leafs’ strategy to some degree. We noted continually how Nazem Kadri did not thrive in this soft-start role and while the Leafs do match Auston Matthews up against top six lines, they look to do so in favourable positions. The fourth line was left with heavy defensive zone starts, like most teams.

That’s where I’m still trying to figure out the Leafs plan – are they going to load up Jason Spezza with heavy defensive zone starts? Nick Shore? Nic Petan? That would seem like strange deployment. Making your star offensive players play more in the defensive zone so that your fourth line can get more offensive zone starts is suboptimal. As has been noted a number of times, in successive years, the Leafs acquired Brian Boyle, Tomas Plekanec, and then were heavily rumoured to be in on Luke Glendening. It’s pretty clear what the Leafs look for in that role come playoff time, but it’s not clear how they are actively trying to solve it during the summer so far.

– When the Leafs traded for Tyson Barrie, I wrote that based on contract, position, and ability to play against top players, Nazem Kadri was the best player in the trade. The value certainly reflects that as the Avalanche had to kick in a legitimate, established NHLer to make the deal while the Leafs included a somewhat-promising defenseman that is also 25 and has eight NHL games on his resume in Calle Rosen. Here is where things get tricky with the deal: If Barrie has a huge year (and he has been a .79 points per game player over the last two seasons, so I don’t see why he wouldn’t), he is going to price himself in at least the $7 million-plus range.

For reference, Tyler Myers got $6 million per year this summer and a somewhat broken, 33-year-old Anton Stralman got $5.5 million per year. Some quick math says the Leafs projected cap hit for next year is around $55.5 million right now, not including any sort of conclusion to the Mitch Marner saga. So that could be around $65 million, plus perhaps $7 million for Barrie pushing them to the $72 million range or so.

Only Morgan Rielly is under contract on defense next year in addition to RFA control on Travis Dermott. You can potentially add in Rasmus Sandin and Timothy Liljegren on entry-level deals, which would be helpful for the cap, but they would still need more quality defensemen. That would leave three or so forwards needed to fill out the roster (they’d have 10 under contract with Marner), plus another three to four defensemen and a backup goalie with maybe $10 million to spend. That would also likely price Jake Muzzin off the team unless they free up money elsewhere.

It’s just tough to see how it turns out well in the long-term if we’re looking at the overall situation today. And if they do sign him to that money and make it work, I’d probably argue he’s overpaid as a second pairing point-producing defenseman (unless he suddenly shows he can be a true top pairing defenseman). So it’s a tough spot. For this current season, I like Barrie a lot, though.

– You can also likely argue that if the season is going well — with Marner in the fold and clicking, coupled with a pretty good core on defense (with two of their best three being pending unrestricted free agents) — this is a good year to make an aggressive move for an over-the-top type of acquisition. There is a lot to be sorted out before then, obviously, but John Tavares is about to turn 29 and Frederik Andersen is about to turn 30 this year. At some point soon, history generally tells us these players are going to decline. Plus, can they really afford to lose in the first round for a fourth straight year? I don’t care who they play at this point, they have to win a round here and go somewhere in the playoffs.

– At the end of the Mats Sundin Leafs era, every trade deadline, fans would clamour for the team to be in on acquiring certain players (just to get into the playoffs) when really, the organization just didn’t have the asset ammunition to get it done. Today, the organization has a number of assets they can dangle to pretty well be in on any deal they so choose (cap considerations aside). They have good young players already in the league and a number of good prospects led by two promising defensemen, but they do lack a first-round draft pick this upcoming year due to the Patrick Marleau trade. They have their second, Columbus’ third, Ottawa’s third, their fourth and Vegas’ fourth, no pick in the fifth, their sixth, Carolina’s and Colorado’s sixths, and four seventh-round picks. If they really want to, they can push their chips into the middle of the table here. And this isn’t intended as a doom and gloom statement that they absolutely should do it now – it’s more to say I think they are reasonably close on paper and have a chance to make a serious run this year.