The Toronto Maple Leafs front office and coaching staff have largely now been rebuilt, even though the team still lacks an official general manager (whoever it ends up being, Brendan Shanahan will likely have final say on major decisions based on the input of everyone).

The rebuild of the player roster has barely started. Obviously, there will be some tough decisions to make, and the answer to those tough decisions largely revolves around when one believes the window of opportunity opens for the Leafs to compete for the Stanley Cup.

The Leafs actually have some pretty good players in the organization, but it is a very poorly assembled team and lacks quality depth. The strength of the team is on the wings with Kessel and JVR, and the key to winning in the NHL is strength down the middle. For perspective, here are the top centers of the Stanley Cup finalists over the past eight seasons.

  • Jonathan Toews (3 times)
  • Anze Kopitar (twice)
  • Pavel Datsyuk (twice)
  • Sidney Crosby (twice)
  • Patrice Bergeron (twice)
  • Tyler Johnson
  • Derek Stepan
  • Travis Zajac
  • Henrik Sedin
  • Mike Richards (when he was good)

Toews, Kopitar, Datsyuk and Bergeron are probably the best two-way centers of the past decade, while Sidney Crosby is a generational offensive talent. Those are the guys who lead teams to Stanley Cup contention. Johnson and Sedin are high-end offensive players as well (as is Stamkos), and Stepan, Zajac and Richards are (or were) very good two-way centers. In addition, most of these Stanley Cup finalists had very good second and third line centers.

DENVER, CO - NOVEMBER 6: Tyler Bozak #42 of the Toronto Maple Leafs skates against Jamie McGinn #11 of the Colorado Avalanche at the Pepsi Center on November 6, 2014 in Denver, Colorado. (Photo by Michael Martin/NHLI via Getty Images)
DENVER, CO – NOVEMBER 6: Tyler Bozak #42 of the Toronto Maple Leafs skates against Jamie McGinn #11 of the Colorado Avalanche at the Pepsi Center on November 6, 2014 in Denver, Colorado. (Photo by Michael Martin/NHLI via Getty Images)

The biggest flaw with the Leafs the past several seasons has been their significant weakness down the middle. Bozak, who may not be a good third line center, has been filling the hole as first line center. Previous management made a poor decision to buy out Grabovski who, while not a true #1 center, was a good two-way center and at least gave the Leafs some depth down the middle. For me, the rebuilding of the Leafs has to revolve around finding an elite #1 center. Unfortunately, a team (generally) can’t trade for those guys and they don’t generally become unrestricted free agents (we can hope for Stamkos, but I wouldn’t count on it). It’s obvious teams largely need to draft and develop them. Everyone on the list above was drafted by the team they reached the Cup Finals with, except for the undrafted Tyler Johnson.

So, until the Leafs find a true elite level #1 center (I really like Kadri, but he isn’t elite level), there is no reason to even consider the team serious Stanley Cup contenders. Since you aren’t likely to find these guys via trade (though very good, Ryan O’Rielly isn’t likely that guy, either) or free agency, it means drafting and developing them. The best case scenario is either Nylander (less likely) or whomever they draft fourth overall next week becomes that guy. Under that scenario, the Leafs could be contenders in as early as three seasons from now if everything else goes right. More likely, we are looking at the window for being true Stanley Cup contenders starting to open up in the 4-6 year range. So, when we are looking at making decisions for the rebuild they must be made with the following goals in mind:

  1. Who will still be significant contributors to the team starting four years from now?
  2. How will this decision aid the team in acquiring (drafting and developing) that much needed elite-level center?

With that in mind, let me look at the Leafs core roster.

The Keepers

PHILADELPHIA, PA - MARCH 28: Wayne Simmonds #17 and Tye McGinn #15 of the Philadelphia Flyers battle next to their bench for the puck with Nazem Kadri #43 of the Toronto Maple Leafs on March 28, 2014 at the Wells Fargo Center in Philadelphia, Pennsylvania. The Flyers went on to defeat the Maple Leafs 4-2. (Photo by Len Redkoles/NHLI via Getty Images)Nazem Kadri
Kadri has had a roller coaster of a career with the Leafs thus far, but all statistical evidence points to him being a good to very good player. He isn’t going to be the elite #1 center, but he will only be 25 next season. He could be a very good #2 center when the Leafs are ready to compete.

Jake Gardiner
TORONTO , ON - DECEMBER 4: Jake Gardiner #51 of the Toronto Maple Leafs runs into Jacob Josefson #16 of the New Jersey Devils during NHL game action December 4, 2014 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images)I am not sure Gardiner really gets the credit he deserves. I really need to write an analytics post on him, but in my opinion he is probably the Leafs best (two-way) defenseman. He’ll be turning 25 in a couple weeks and is on a very reasonable long-term contract (4 more years at just over $4M/yr). Trading Gardiner would be a mistake.

Morgan Rielly
Morgan RiellyRielly’s offensive ability has been obvious from his first game in the NHL, but early on he struggled on the defensive side of the game (nothing out of the ordinary). He showed progress defensively last year and, if he continues to improve, his upside is huge. Rielly is the least likely player to be traded, and for good reason.


Players that should/will be moved

Dion Phaneuf
Pittsburgh Penguins v Toronto Maple LeafsAs the captain and leader of a team that drove the truck off the cliff several times, he probably needs to be moved. Add in the fact that he is entering his 30s with a big $7M cap hit for six more seasons, and he needs to be moved while he still has decent value. The latter years of his contract might end up being terrible value and that will be when the Leafs will really want to be competing for the Stanley Cup. He needs to be moved this off season.

Tyler Bozak
Tyler BozakBozak should not be on this team next season. End of story. Even if he is good enough to be the third or fourth line center, he is symbolic of everything that has been wrong with the Leafs the past several years. There may be some teams that see value in him; if there are, the Leafs need to get whatever they can for him.

Joffrey Lupul
Joffrey LupulI am a Lupul fan, but at age 32 he won’t likely be a productive player when the Leafs are ready to compete, even if he can stay healthy. With that said, I don’t think there is an urgency to trade him this summer either as his trade value is low right now coming off a poor season, and he is set to earn $6.75M ($5.25M cap hit) next season. He may very well have more trade value at the trade deadline or next summer if he can have a good, and mostly healthy, season.

Roman Polak

Photo: NHLI via Getty ImagesI am not a Polak hater as some are, but if you can get something decent for him you, make the trade. If not, you wait until the trade deadline, but he has no long term future with the Leafs.

Unmovable Players

Stephane Robidas
If you can move Robidas you do so immediately, but there is probably no hope of that happening without taking an equally bad contract back. That said, they did trade David Clarkson, so here’s your customary “you never know.”

Wait and See

James van Riemsdyk

TORONTO, ON - DECEMBER 9: James van Riemsdyk #21 of the Toronto Maple Leafs skates the puck away from Kris Russell #4 of the Calgary Flames during NHL game action December 9, 2014 at the Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images)

JVR is only 26, is on a good contract (three more years at $4.25M), and should still be able to contribute when the Leafs are ready to contend again. There is no reason to trade him just yet unless it returns a player/prospect that has the potential to be an elite first line center for the Leafs for the next decade.

Leo Komarov
Toronto Maple Leafs Leo Komarov celebrates  after Tyler Bozak scores a shorthanded goalHis salary is too high for a third line player, but I really like what he brings to the team in terms of the energy he brings to the game, the willingness to play defense, and his ability killing penalties. I think these are important attributes to have on a rebuilding team. Let’s see what he does over the next couple seasons and then decide what value he might have as a role player beyond that.

Extra Parts

Peter Holland & Richard Panik
We still don’t know whether these guys will develop enough consistency offensively to warrant a top 6 role, but they are cheap, young-ish players who have played well enough to earn more ice time as some of the top six guys are traded away. This is especially true of Holland, who looks like he can become at least a good two-way third line center.

The Goalies
Both goalies are going to be 27 next season, meaning they will be into their 30s when the Leafs are ready to seriously compete for a Stanley Cup, if not well into their 30s. For Reimer, who isn’t looking like he is a reliable starter entering into his prime years, there is little chance he will be when the Leafs are contenders. There is a little more likelihood that Bernier will be a good enough starter four or five years from now, but that is far from certain. The Leafs don’t really have anyone on the verge of taking their jobs, so there is a strong possibility that Bernier and Reimer are the Leafs goalies next year. Long term it is difficult to say, as goalies are hard to predict and the goalie market in the NHL is a strange one these days. It’s likely the Leafs stick with Bernier and Reimer for a few years and see how they and the rest of the team pans out. No rush to make any significant moves in goal yet.

The Big Question Mark – Phil Kessel

Phil Kessel
TORONTO, ON – JANUARY 9: Phil Kessel #81 of the Toronto Maple Leafs scores on Sergei Bobrovsky #72 of the Columbus Blue Jackets during game action on January 9, 2015 at Air Canada Centre in Toronto, Ontario, Canada. (Photo by Graig Abel/NHLI via Getty Images)

Leave the best to last. This is the guy everyone is torn on what to do with, and understandably so. There is no doubting his talent. Over the past four seasons, he has the fourth most goals (trailing only Ovechkin, Stamkos and Perry) and is 20th in 5v5 goals/60. He is an elite offensive player. There is a lot to like about Kessel.

The downside with Kessel, though, is that he is for the most part an offense-only player. Defensively, he is probably below average, and when he was asked to play a better puck possession game under Horachek (which, to his credit, he and the rest of the top line did) his offense dropped off significantly. He is also a winger, which is probably the least important position on the team. The question is, does it make sense to be paying $8M/yr to a largely one-dimensional winger at this stage of the Leaf rebuild?

Kessel will be 28 this season, so he will be well into his 30’s when the Leafs are ready to compete, and will be 34 in the final season of his contract. Between now and then, several players will be looking for new, and possibly big, contracts including Kadri, Gardiner, Rielly, JVR, Nylander, and of course they hope to have an elite first line center that might be earning $10M+ by then. Kessel earning $8M/yr at age 32, 33 and 34 five, six and seven years from now is a luxury they may not be able to afford at this point.

For me, I think Leaf management has to be evaluating all options with Kessel (and they appear to be doing just that). Although he is their most skilled forward and should still be a great offensive player for a long time yet, you have to plan for the possibility that Kadri, JVR, Gardiner, Rielly, Nylander, and whomever the Leafs draft 4th overall next week will be earning big dollar contracts five years from now, and that five years from now they may all be as or more important to the Leafs than Kessel will be. Besides, if those guys aren’t earning big dollar contracts (because they aren’t good enough to), the Leafs won’t be contenders and won’t need Kessel anyway. For that reason, Leaf management must explore trading Kessel. They don’t need to trade Kessel this summer, but there is a strong argument to be made that it is in their best long-term interests to do so. The return will be big and may include a prospect or a draft pick that might end up being that elusive elite #1 center.

Short Term Rebuild Tactics
There will end up with a lot of salary cap space to work with if the Leafs are able to trade some number of Phaneuf, Lupul, Bozak, Kessel or Polak this off season. This will put them in good shape considering the number of teams that are up tight against the cap, and they will have an ability to make some interesting moves in both the free agent market and in the trade market.

There isn’t much in the unrestricted free agent market that the Leafs should be looking to sign long-term, but if they do trade Phaneuf I think they should take a look at bringing Cody Franson back if the dollar amount is good (under $5M/yr would be a steal). The real value for the Leafs will be waiting until August and signing players of the Winnik and Santorelli ilk to one or two year deals. Bring them in, play them a lot, and then flip them for draft picks at the trade deadline. It is hard to predict who those specific players will be this summer, but there will be bargain bin options sitting around in August looking for contracts that can be had for $1-2M and could net the Leafs a second or third round pick come March.

The other thing the Leafs can do with the extra cap space is take on contracts from another team. For example, the Boston Bruins are up tight against the cap and Doug Hamilton needs a new, and likely big, contract, plus they have a number of other roster spots to fill. They also happen to have Chris Kelly set to earn $3M next year as their third line center. The Bruins may very well be willing to send the Leafs a prospect and/or a 3rd round pick if the Leafs took Kelly off their roster. Kelly is still a useful player and come the trade deadline the Leafs could flip Kelly to another contending team for another 3rd or 4th round pick, especially if the Leafs played him a lot to boost his ice time and stats. There other players the Leafs could look to do this with as well. Brian Bickell of the Blackhawks, or PA Parenteau of the Canadiens; Colin Greening and David Legwand of the Senators.

The key to contending over the long haul is building a solid pool of young players to replace the older guys that become too expensive. Ultimately, building that prospect pool is what must begin this summer as it takes 3-5 years to turn a draft pick into a contributing team member. In large part, this will be accomplished by the trades they make for Phaneuf, Bozak, Lupul, Polak and possibly Kessel, but being creative with extra cap space is another important step in that process. It will be an interesting summer for the Leafs, to say the least.