Let’s take three strands and tie them together.

The Leafs are poised to be players in free agency this summer, with a spectacular amount of cap space on top of LTIR flexibility from the Horton and Lupul contracts. The Leafs appear to be rebuilding somewhat ahead of schedule—or if you prefer, they’re rebuilding on the fast schedule that (we hope) compares to teams like Chicago. They’re poised to jump 25 or so points over last season, and up perhaps 15 spots in the standings. That is an incredible and rare feat. The Leafs’ cap space is likely to shrink dramatically by the beginning of the 2019-20 season. William Nylander will require a second contract starting summer 2018; Auston Matthews and Mitch Marner will require new deals for summer 2019. Given all three of them have established their NHL talent very early, we can expect their first restricted free agent deals to be enormous. This is before we even consider key pieces like James van Riemsdyk (if he’s still here, UFA 2018) and Jake Gardiner (UFA 2019), as well as intriguing young players like Connor Brown (RFA 2017) and even Zach Hyman (RFA 2017.) Everyone in this paragraph currently looks likely to get a raise.

So: the Leafs look set to be good next year and the year after and they have a ton of cap space that will subsequently go away.

Why not look for a big impact UFA and offer him an enormous amount of money for short term, and see if we can make this team a contender right now?

I’ve seen variations on this idea suggested several times lately, but the most recent example was by PPP commenter Tanoki:

We should sign Shattenkirk to a two year contract for ALL of our cap space with a handshake that after two years he’ll sign to a five year deal under market value. Pack as much cap hit into the first two years as possible.

To lay it out a little more formally: the Short Max idea is to take a very highly desirable UFA who fills a need and offer him close to the maximum possible contract for two seasons.

For the purposes of this article, we’ll take it for granted that Shattenkirk is the sort of player we’d consider giving this kind of offer to. Let’s look at it.

The Max Contract

The maximum salary for any single year of a deal is laid out by Article 50.6 of the CBA, and it’s pretty simple: 20% of the total team salary cap. Currently the team salary cap is $73,000,000; the maximum annual player salary is $14,600,000, which includes all salary and bonuses.

Note on that: the deal has to explicitly lay out a dollar value (you can’t just offer a player 20% of the max, so that his salary varies with the cap.) Other thing: every year of the deal has to be compliant with the max for the year in which it’s signed. Say, in a total hypothetical, we offer some UFA a seven-year deal at the max in a year where the cap is $73M. The max the player can get paid in real dollars in any year of the contract is $14,600,000. It doesn’t matter if the cap goes up to $78M a couple years later and raises the max by that point; our deal was signed in a $73M cap world, so those are the rules we have to play by. (This also prevents a contract from becoming illegal after the fact if the cap declines, though this has never happened so far.)

Bottom line: Let’s assume the max we can give an FA on a two-year deal is about $14.6M per year.

Has Anyone Signed A Deal Like This Before?

Short answer: no.

No one in the NHL has a cap hit greater than $10.5M, for Patrick Kane and Jonathan Toews. Toews and Kane actually make more than that in real dollars this season ($13.8M apiece), but the deals decline in value in the subsequent seasons. Considering these are both eight-year extensions signed with a Cup team, they have no connection at all to our Short Max UFA scenario.

There are 74 players in the NHL with cap hits of at least $6,000,000 per season. 64 of them (86%) are on deals at least five years in length. None of them are on deals shorter than three years.

Of that group, the guys on three year deals are all either old or unhealthy. Here’s the list of the players on them, with the age they were at the start of the first season of the contract: Mike Green (30), Ryan Miller (34), Tomas Plekanec (33), Joe Thornton (35), Patrick Marleau (35), and Pavel Datsyuk (36). Aside from Mike Green, who is a byword for “injury-prone”, all of these were deals for guys in their mid-to-late 30s, for whom no team wants to take term risk. This has basically no application to a Short Max situation; the kind of player in mind is usually a player in his late 20s.

There are four four-year deals on the list. Three of them are more “too old for full term” players—Henrik and Daniel Sedin (34) and Jason Spezza (32). The last is St. Louis Blues centre Paul Stastny, who appears to be the only UFA to start a high-value contract of four or fewer years in his 20s (29.) Stastny probably would have been well advised to get more term, considering his production is well down from his peak (he scores at about the rate Tyler Bozak does.) On the other hand, $7M a year ain’t bad, and he is, or was, on a Cup contender.

Essentially there is no precedent for a deal of the kind we’re talking about. If you want to try very, very hard, you can argue Alexander Radulov signed a reasonably expensive deal for one season ($5.75M), but Radulov clearly had a ton to prove coming back from the KHL and probably wasn’t getting term out of anybody. And this is a hell of a lot less money than we’re discussing.

The fact no one has done this doesn’t make it impossible, but it should give us pause. GMs and player agents can read the CBA as well as we can, and they’ve tried all sorts of creative deals in the past—take a look at the Kovalchuk contract. Let’s try to think about why they would, wouldn’t, or couldn’t try something like the short max.

Contract Risk

As a rule, players want term as UFAs. This makes sense. Hockey is a dangerous game, and health today does not guarantee health tomorrow. Marc Savard’s career has ended tragically; it would have been even more tragic for him had he signed a one-year deal before getting injured.

Short-term deals offload this risk onto the player. Kevin Shattenkirk may be worth seven years at $7M today; in a few years he may get injured beyond repair, or he may just get old. Maybe Shattenkirk—or whoever else you want to name—really believes in himself to the extent that he thinks he’ll be a 1D well into his 30s, like Nik Lidstrom. But everything we know about aging curve suggests he’s very unlikely to do that, especially as a non-generational player.

$14.6M x 2y guarantees Shattenkirk $29,200,000 in pre-tax income (this is without considering fees and escrow and a thousand other things, but we won’t worry about those for the moment.) $7M x 7y guarantees him $49,000,000. That’s a hell of a difference.

Okay, but maybe he’ll sign a deal after that that will result in him making more money in the end. (This, by the way, is where I note I don’t think a handshake deal to do anything after the two years makes any sense. Putting aside that a handshake deal would be cap circumvention under the CBA and an extremely uncertain bet, Shattenkirk probably needs to make close to as much money as he can on his next contract for this setup to be more profitable.) But even if he’s choosing between $49M guaranteed and $29.2M plus potential, certain money is worth more than uncertain money. And with the increasing unwillingness of teams to give term to guys in their 30s, would you want to bet on that potential?

Circumstances

Of course, there’s another reason these deals don’t happen much. Teams rarely have the cap space to offer max deals, combined with the money to actually pay for them, at a time when the team is good enough to justify offering one. Further to that, for the first cap-era Collective Bargaining Agreement (2005-2013), the popular form of “big contract” was an extremely long-term deal with value that cratered in the final years. The implicit assumption was that the player would retire before the final years of the deal anyway, so having a few years at the end with a salary of $1M just served to reduce the AAV. Shea Weber’s contract is a good example of this. Teams could combine offering a massive real salary while limiting the consequences; they could to some extent have their cap and eat it too.

The league did not like these deals, and it went out of its way to destroy them in the 2013 CBA. The new agreement imposed rules capping contract length, limiting variation in AAV, and imposing recapture penalties for contracts where the player retires early. It’s difficult for teams to avoid major cap consequences for big salary-deals, which might make a shot max deal more logical now than it used to be—for the rare team in a position to offer one.

The Leafs’ Side Of The Deal

There’s a reason so many Leaf fans have suggested this deal; fans always want to make the jump to a Cup. The Leafs would legitimately experience a cap crunch in the second year of the contract, because Nylander would need a raise; $14.6M is a really enormous amount of cap space. But the Leafs could make a deal like this work if they really wanted to. The biggest thing might be the psychological hurdle of giving a player a $14.6M cap hit. This front office has prized flexibility to an enormous degree, and Shattenkirk on a deal of this nature almost totally removes that. We become committed to winning with this team + Shattenkirk + small changes, and that’s a big gamble. I’m not sure our team would be willing.

Still, Lou is an inventive GM, and maybe he’s one of the ones who’s willing to go outside the box enough to attempt something like this. I don’t know that either side would be willing to sign this deal, but the Leafs have more incentive to do it than Shattenkirk does.

Are We Appealing? ;)

Turning back to the player’s decision-making, this deal gets more appealing to the free agent if the team can present him an excellent chance of winning a Stanley Cup. The Leafs actually can probably offer a player a better chance of winning a Cup in addition to a short max contract than anyone else. Teams close to contention don’t tend to have $14M to throw around, which is another reason we’ve never seen a deal like this.

But if the player is very determined to win a Cup, there are probably better options with teams willing to offer a more conventional deal. The Leafs, for all their excitement, are at best a middling team in the process of improving. Edmonton has had false dawns before, too; while I think the Leafs have a more secure road to success because their underlying offensive numbers seem to be legit, it’s still a lot to tell a free agent “I know we were 30th a year ago, I know we’re only mid-level now, but with you we think we’re the Blackhawks.” It’s not impossible! But it’s hard to say whether any particular player would find it persuasive.

A Certain Type Of Player

If you got a player who really wanted to play in Toronto, who was very confident about his ability to gain a subsequent contract and not risk-averse, who believed in the Leafs’ rebuild and that he could boost them all the way to Cup contention, you might conceivably get a deal like this. You’d also have to have a front office who believed the time had come for very aggressive moves. This perfect set of circumstances is obviously not common.

Unprecedented is not impossible, and everything that happens has to happen for the first time. But in the end, I can’t see this contract either being offered or being accepted.