I am not sure we’ll see a tougher test of Kyle Dubas’ cap discipline outside of the big core four than this upcoming Zach Hyman contract negotiation — at least not until a possible Morgan Rielly negotiation in 2022.

It goes without saying that Dubas’ entire thesis behind his roster construction and cap allocation relies on a high degree of ruthless efficiency throughout the rest of the roster. We’ve seen mid-tier players (salary-wise) the Leafs would’ve liked to have kept squeezed out of Toronto a number of times already, be it Kasperi Kapanen (trade), Andreas Johnsson (trade), Tyler Bozak (walked as a UFA), Jake Gardiner (UFA), or James van Riemsdyk (UFA).

Ideally, Hyman makes Dubas’ life easier by sitting down to hammer out a number that works for the two sides in the next month rather than playing wait and see while approaching this as a negotiation with 32 teams, including the Leafs. On paper, Hyman would seem to fit the profile of someone who would consider taking less to stay at home, but he is obviously under no obligation to as a pending UFA — and he is 100% within his rights to argue that no one else on this team has sacrificed anything financially outside of Jason Spezza (who is obviously in an entirely different situation) and maybe Morgan Rielly many years ago. Plus, Hyman has been playing on a bargain contract for three seasons now.

It’s not a fun conversation, but we cannot strip away the context of how contracts have been handled by this management group to date, either. It’s not the literal $1.5-2 million Mitch Marner is overpaid by that is the really uneasy part here — it’s the culture it creates when the top earners refuse to make even a nominal sacrifice for the sake of the team.

You can argue that Marner and his agent were well within their rights to scratch and claw for every penny, but to be clear, the unyielding “I’m getting mine” attitude was definitely not how the organization saw this playing out. We know this because of a telling quote from Brendan Shanahan when the William Nylander standoff was underway back in 2018.

“When I get together with some of my old mates from the Cup years in Detroit, we talk about winning together and growing together, and that’s what we remember,” Shanahan said in early October of 2018. “We all found a way to fit with each other so that we could keep adding to the group… That’s obviously what we’re asking some of our young leaders to do.”

Shanahan took some heat at the time for making the comparison to his pre-cap-era Red Wings teams, but it’s clear the organization thought it would get more buy-in than the reality that played out, which outside of Auston Matthews’ negotiation — who still only signed for five years at an AAV many thought would buy more UFA seasons than just the one — was about as contentious and ugly as it could have gotten.

We’re continuing to see the many ramifications of all of this play out as recently as this past week. The goodwill Marner has built up within the market when he under-performs in the playoffs is non-existent, and it’s largely his own camp’s fault (smarter advice would have allowed the details of the big contract demand to leak to the media before taking a bit less to appear as though he sacrificed for the sake of the team in the end — a la Connor McDavid — and then made up the difference with Marner’s 45th Intact Insurance commercial).

Beyond all of the above context, with his 29th birthday coming in a few days, the biggest factor is that this is Hyman’s first and only chance to hit a homerun coming off of 36 goals in his last 94 games spanning the last two regular seasons (a 34-goal pace in 2019-20 and a 29-goal pace in 2020-21).

As far as the comparables, the Hyman camp could look at Josh Anderson’s contract (7×5.5) and the Leafs could look at Tyler Toffoli’s contract (4 x 4.25), although neither applies perfectly to Hyman’s situation.

I see Jakub Silfverberg’s deal as a strong comparable for a number of reasons: both are high-utility wingers who can play all situations (PK + PP), are reliable defensively, scored in the 25-30 goal range (as an 82-game pace) in their contract seasons, generally battle injuries, and both were/are due up as pending UFAs turning 29 years of age. Silfverberg’s five-year, $5.25 million AAV leaves him a little overpaid, although factoring into the Ducks’ calculations is the player’s history of significant playoff production — 18 points in 16 games in 2015, nine goals and 14 points in 16 games in 2017.

In a situation that requires tradeoffs, as Chris Johnston wondered aloud recently, maybe the Leafs go the Alex Killorn route by uncomfortably stretching the term to seven or eight years to keep the AAV down — preserving the Cup window created by the Marner and Matthews contracts above all else, at the expense of locking in Hyman all the way until his 36th or 37th birthday. The Leafs can build in the usual escape hatches with a heavily front-loaded and signing-bonus-laden deal, with the hopes that league revenues will be thriving again post-pandemic economics.

The clear reasons for caution here center around not only Hyman’s age but also his injury history. While he certainly seems like more of a playoff player than not, he also has just five points in his last 19 playoff games (13 in 32 overall). But there is a significant emotional attachment to this player for both the organization and fan base, and he is very difficult to replace when we account for his all-situations utility and role versatility — both his ability to drive a checking line if needed, and his obviously strong complementary fit alongside any of the team’s top-six offensive duos (over the years, he has shown that Matthews-Nylander, Tavares-Marner, and Matthews-Marner are all better with Hyman than without).

Anything in the $4.25-$4.75 million range is palatable, but if you’re getting too far north into the 5s or mid-5s, this starts to get very tough.

I don’t envy Kyle Dubas’ job in moments like these, but getting these kinds of decisions right is where his big bet can be won or lost.

Expansion Draft Ramifications

There are also some interesting expansion considerations depending on how (and when) this Hyman contract shakes out.

With Hyman signed before protection lists are due on July 17, the Leafs would have to protect five forwards, and they will therefore have to shift to the seven forwards, three defensemen, one goaltender protection scheme, with Justin Holl exposed (there is no sense in the eight skaters, one goaltender scheme if five forwards are included, leaving you with just three defensemen to protect anyway — Rielly, Muzzin, Brodie. You would sooner add Kerfoot and Mikheyev or Engvall to the protected list, with Holl exposed).

If Hyman isn’t signed by then — which creates the risk of allowing Ron Francis and the Kraken to negotiate with the player prior to the expansion draft — it makes the 8 + 1 protection scheme with Justin Holl protected and Alex Kerfoot exposed the likely play.

Holl vs. Kerfoot could be debated, but I’d urge us all not to get too far ahead of ourselves based on Kerfoot’s seven-game playoff sample versus Montreal.

To his credit, Kerfoot stepped up with John Tavares out injured, played well at center, produced six points in seven games, and became a player Keefe relied on in critical late-game situations when protecting the lead throughout the year. There isn’t a strong appetite in this market at the moment to surrender players who actually stepped up in the playoffs, regular season performance be damned.

But Kerfoot is paid $3.5 million and has produced like a 35-point player — and that’s with a fair amount of opportunity on John Tavares’ wing over the past two seasons.

While Holl slowed down as the season progressed and may not be a full-time top-four defenseman if he’s not paired with Jake Muzzin, he’s right-handed and has been a stable partner for the Leafs’ best 5v5 defender inside the top four. The two have consistently delivered positive results playing tough minutes, and he’s owed $2 million a year for the next two seasons.

This might make for something of an open-and-shut case: Holl recorded three fewer points than Alex Kerfoot in one fewer game this past regular season (20 points for Holl, 23 for Kerfoot).

If Seattle selects him, Kerfoot’s production can absolutely be replaced for less than the $3.5 million he’s owed, and the difference could help offset the Hyman raise.

Of course, whether it is Holl or Kerfoot, Dubas could incentivize Francis to steer clear of them in a side deal, but with Vegas on yet another deep playoff run as of this writing, we need no reminding of how carefully the league’s other 31 GMs need to tread here.