I have always been a long-term planner even though this trait does not synchronize with the prototypical short-term view–typically defined as the win now at the expense of the hockey club’s future mentality–of Leafs Nation. This means that if I were hired by Brendan Shanahan to fill the current vacant GM position of the Toronto Maple Leafs hypothetically speaking, rather than agonizing over the fact that the Blue and White came out on the short-end of the stick in the 2015 NHL Draft Lottery, or unrealistically trying to figure on how to go about convincing Edmonton Oilers GM Peter Chiarelli to trade Connor McDavid to Toronto before the commencement of the 2015 to 2016 NHL season, I prefer to spend my time on analyzing whether there may be a way to put No. 97 in a Maple Leafs jersey at the first available opportune time instead.

Timing Is Everything:

While there is no absolute guarantee, all signs point to the fact that McDavid will be an impact player in the NHL. There have been extensive media coverage detailing how he will inevitably become the next face of the NHL as a can’t-missed generational talent. Indeed, all-time NHL scoring leader Wayne Gretzky, who amassed an incredible 2,857 points over a 20-year career from 1979 to 1999 with stints in Edmonton, the Los Angeles Kings, the St. Louis Blues, and the New York Rangers, described McDavid as the best prospect in the past three decades (along the same calibre as Mario Lemieux and Sidney Crosby) so I will not waste writing space repeating what is already obvious.

Wayne Gretzky says NHL prospect Connor McDavid is “the best player to come into the league in the last 30 years.” » http://t.co/Zwwjydbgks — SportsCenter (@SportsCenter) April 22, 2015

Given McDavid’s expected elite offensive production for years to come, his tender age, his club-friendly salary dictated by his three-year entry level contract, and how marketable he is already not to mention all the intangibles (e.g. how his mere presence would increase the confidence and morale of the team/long-suffering fan base and by all account, bring the best out of his linemates and teammates), there is next to no chance that the Oilers would trade McDavid at this point, at least not willingly. As such, it is simply a waste of time to make phone calls to Chiarelli to try to convince him to somehow change his mind and trade McDavid no matter how attractive the returns may look–yes, that means Toronto will almost certainly get rebuffed even if they were willing to put Mitch Marner, William Nylander, and Morgan Rielly on the table simultaneously as part of the package in a possible deal for McDavid.

A realistic strategy is to keep an eye on McDavid and strike in three years time when the first opportunity presented itself. Three years from now, McDavid becomes a restricted free agent assuming that Edmonton does not resign him before he completes his entry level contract. By that time, the Oilers may well have difficulties getting itself under the salary cap as Edmonton have already committed $22,000,000 to just four players for the 2018 to 2019 season: Jordan Eberle ($6,000,000), Ryan Nugent-Hopkins ($6,000,000), Taylor Hall ($6,000,000), and Benoit Pouliot ($4,000,000). Even if the Oilers is willing to spend the maximum allowed, i.e., at the salary ceiling, for the 2018 to 2019 season, it would be a tall order to fill out the reminder of the roster (totalling 19 players, especially with players such as Nail Yakupov expecting a big raise on his second contract) seeing that the team has already tied up so much money on just four players. As such, Edmonton could face major challenges trying to free up enough cap space to resign McDavid by that time, much like how the Pittsburgh Penguins have little salary cap room to manoeuvre now having devoted a significant percentage of its salary cap to five players: Crosby, Marc-André Fleury, Phil Kessel, Kris Letang, and Evgeni Malkin. In fact, the Oilers could find itself in cap jail, a situation that is reminiscent of how the Chicago Blackhawks had to dispatch key members of its Stanley Cup-winning teams in 2010, 2013, and 2015 having spent a large portion of its cap space to lock up Patrick Kane, Ducan Keith, Brent Seabrook, and Jonathan Toews.

There is a caveat: This window of opportunity may never open if McDavid were to resign with Edmonton after the second year of his soon-to-start three-year entry level contract. However, if the chips were somehow fall into place whereby (1) the Oilers does not kick start contract extension talk with McDavid’s agent (and vice versa) before McDavid’s three-year entry level contract expires or (2) the two parties somehow cannot come to an agreement (e.g., on the term and/or dollar amount) on a new deal, then the stars would align for the Maple Leafs as we would arrive at the first realistic opportune time for Toronto to try to pluck McDavid away from Edmonton.

Taking Advantage of A Team In Cap Jail:

Since the implementation of the salary cap in the 2005 to 2006 NHL season, the Maple Leafs has arguably been the biggest loser under the new system because they can no longer flex their final might to mask their management short-sightedness, i.e., by trading away valuable draft picks for short-term help in order to clinch a playoff berth and then over-spend on unrestricted free agents to compensate for the lack of home-grown talent. Yet, this is one rare occasion in which Toronto maybe able to utilize the rules of the salary cap to their advantage: by tabling an offer sheet that is higher-than-market value, long-term, and heavily-frontloaded to McDavid when and if he makes it to unrestricted free agency after the 2017 to 2018 season.

Of course, conventional wisdom dictates that the Oilers would do everything in their power to keep McDavid, even if t means sacrificing the likes of Taylor Hall, Ryan Nugent-Hopkins, Nail Yakupov, and /or Jordan Eberle by trading them for undervalued packages in order to free up cap space and then use the precious room to resign McDavid. However, as Chicago and the Boston Bruins’ recent cost-cutting measures have demonstrated, a hockey club may not be able to keep a player if it is in cap jail and have no choice but to rid themselves of key members (e.g., Blackhawks GM Stan Bowman traded Brandon Saad to the to the Columbus Blue Jackets and Patrick Sharp to the Dallas Stars in separate transactions whereas Boston GM Don Sweeney traded Dougie Hamilton to the Calgary Flames and Milan Lucic to Los Angeles despite the fact that neither GMs wanted to move these players.

Another factor to consider is that even if Edmonton manages to shed enough salary and free up the necessary cap space to try to resign McDavid, there is no guarantee that McDavid would be willing to resign, especially since he has already made it clear that it be a dream come true for him to play for the Maple Leafs (albeit both Dylan Strome and Marner have the same mentality). Under this circumstance, the Oilers essentially has two options: (1) to engage in a hostile (and possibly lengthy) contract dispute with McDavid which would result in a stalemate for both parties (and in turn give rival teams the chance to submit offer sheets to McDavid) or (2) to trade McDavid for assets that could help the club immediately and/or down the road. Leading up to the 2015 NHL Entry Draft, the Bruins wanted to resign Hamilton (and in fact put a fair offer on the table) but due his fear of looming offer sheets heading Hamilton’s way (scenario 1), Sweeney acted swiftly by trading the young star defenceman to Calgary on draft day (June 26, 2015) even though the return–(a first-round pick (15th overall) and two second-round selections (45th and 52nd overall which the Flames earlier acquired from the Washington Capitals) in the 2015 NHL Entry Draft– has been criticised as being insufficient and underwhelming.

Retribution?

A number of GMs are weary of extending offer sheets to other teams due to the risk of reprisal. For example, former Leaf GM Brian Burke was known for his refusal to use offer sheets (particularly if it is an inflated contract) as a weapon because of the potential retaliation, i.e., if Team A sends an over-valued offer sheet to a star player of Team B, the latter team would return the favour to the former them at some point down the road and the cumulative result is that it would become a never-ending offer sheet war. Likewise, rumours had it that former Leaf GM and Coach Pat Quinn elected to trade 2nd-round draft pick to Boston for Dmitri Khristich’s rights before signing him just to “keep the peace” even though the Bruins were set on walking way from Khristich’s arbitration settlement, which would have granted Khristich unrestricted free agent status (at which point Toronto could simply sign him without having to pay compensation to Boston).

Nevertheless, because the target player, McDavid, is a generational player who in three years from now would still have yet to enter his prime, the Maple Leafs should seriously consider sending him an offer sheet if he arrives at restricted free agency even if it means that vengeance on Toronto from Edmonton is a possible outcome down the road. In short, even if the Oilers were to go after a prized Leaf player (e.g., Marner) as their counterstrike, the Maple Leafs should still be in fine shape. With Toronto in full rebuild mode after the tri-management team of Shanahan, Hunter, and Dubas began the tear down process by shipping Phil Kessel to Pittsburgh not to mention that one or more core leaf players (e.g., Tyler Bozak, Joffrey Lupul, Dion Phaneuf, and James Reimer) are likely on their way out, the team should have plenty of cap space to match Edmonton’s offer sheet to Marner in three years. Even if the Maple Leafs were unable to match the offer sheet for whatever reasons and ended up losing Marner to the Oilers, Toronto would still have effectively ‘traded’ Marner (a likely perennial superstar) to Edmonton for McDavid (a generational talent). This means that the Maple Leafs still emerges as a winner.

Imagine the One-Two-Three Punch

If the Oilers were to corner themselves into cap jail territory and Toronto were successful in signing McDavid after the 2017 to 2018 season via the offer sheet route, image the kind of depth the Maple Leafs would have down the middle with McDavid, Marner, and Nylander centering the first three lines (assuming that the hockey club elects to keep the latter two budding stars at the centre position). To this end, the wishful thinking scenario which I discussed earlier whereby Toronto could afford to play a first-line centre on the second or third line, might just materialize. Sure, the Maple Leafs would surrender a tone of draft picks in successive years to Edmonton (likely four or more first-round picks) as compensation for bringing McDavid to the Leaf fold, but with the nucleus of their top-three lines essentially set for the next decade in McDavid, Marner, and Nylander, Toronto could finally afford to sacrifice draft picks that most likely are going to be late-in-the-round selections given that the team would most likely not only make the playoffs for years to come but in fact go deep in the postseason, if not win the cup. For Leafs Nation, the arrival of McDavid in summer 2018 would mean that the Maple Leafs would finally have its own version of Crosby, Malkin, and Jordan Stall in at the centre position.