Whenever a Maple Leaf signs a contract, you'll be bombarded with a lot of people telling you that it is the single dumbest trade in hockey history. That's not to say that there aren't some issues with his contract. It's a divisive signing but it's hardly a millstone. It was the same song and dance when Grabovski signed (which makes no sense but here we are) when the truth is that the odds that the deal will go that badly are probably long.

But since you're likely to see "Lupul makes more than John Tavares! LOLOLOL" or some variation on that uninformed chirp we should take a look at what names will probably crop up. The table below is drawn from CapGeek and shows the 20 closest comparable contracts. This group is organized by the percentage of the upper boundary of the salary cap that their cap hit represents in the first year of the deal (Cap Pct). This addition to CapGeek comes courtesy of Draglikepull (but not draglikepull2) who made an app to show a better way to look at cap hit deals.

Name Age Team Length Start Expiry Cap Hit Cap Pct Delta
Ales Hemsky 29 EDM 2 2012 2014 $5,000,000 7.12% $250,000
James Neal 25 PIT 6 2012 2018 $5,000,000 7.12% $250,000
Evander Kane 21 WIN 6 2012 2018 $5,250,000 7.48% $0
David Krejci 26 BOS 3 2012 2015 $5,250,000 7.48% $0
Shane Doan 36 PHO 4 2012 2016 $5,300,000 7.55% $50,000
Patrice Bergeron 27 BOS 3 2011 2014 $5,000,000 7.78% $250,000
Mikhail Grabovski 28 TOR 5 2012 2017 $5,500,000 7.83% $250,000
John Tavares 22 NYI 6 2012 2018 $5,500,000 7.83% $250,000
Joffrey Lupul 29 TOR 5 2013 2018 $5,250,000 8.16% $0
Jeff Carter 28 LAK 11 2011 2022 $5,272,727 8.20% $22,727
Tomas Plekanec 30 MTL 6 2010 2016 $5,000,000 8.42% $250,000
Ryan Kesler 28 VAN 6 2010 2016 $5,000,000 8.42% $250,000
Bobby Ryan 25 ANA 5 2010 2015 $5,100,000 8.59% $150,000
Martin St. Louis 37 TBL 4 2011 2015 $5,625,000 8.75% $375,000
Martin Havlat 31 SAN 6 2009 2015 $5,000,000 8.80% $250,000
Brian Gionta 34 MTL 5 2009 2014 $5,000,000 8.80% $250,000
Jeff Skinner 20 CAR 6 2013 2019 $5,725,000 8.90% $475,000
Marian Hossa 34 CHI 12 2009 2021 $5,275,000 9.29% $25,000
Jason Pominville 30 BUF 5 2009 2014 $5,300,000 9.33% $50,000
Phil Kessel 25 TOR 5 2009 2014 $5,400,000 9.51% $150,000
Shawn Horcoff 34 EDM 6 2009 2015 $5,500,000 9.68% $250,000

As you can see by the table, Lupul's the ninth lowest by that measure. Grabovski, obviously, does well by this measure. However, the table has a few players that shouldn't be included. Lupul was going to be an unrestricted free agent this summer so he had the added leverage of being able to wait until that point when he'd be able to talk to all 30 teams instead of just one. Restricted free agents, however, are left with much less leverage. They cannot offer their services on the open market and have to rely on another team presenting them with an offer sheet - except that NHL GMs are mostly afraid of rocking the boat - so their salaries are depressed. On the list above James Neal, Evander Kane, David Krejci, Patrice Bergeron, John Tavares, Bobby Ryan, Ryan Kesler, Jeff Carter, and Phil Kessel were RFAs at the time that they signed their deal. So if we're looking at true contract comparables we'd want to look at the table below:

Name Age Team Length Start Expiry Cap Hit Cap Pct Delta
Ales Hemsky 29 EDM 2 2012 2014 $5,000,000 7.12% $250,000
Shane Doan 36 PHO 4 2012 2016 $5,300,000 7.55% $50,000
Mikhail Grabovski 28 TOR 5 2012 2017 $5,500,000 7.83% $250,000
Joffrey Lupul 29 TOR 5 2013 2018 $5,250,000 8.16% $0
Tomas Plekanec 30 MTL 6 2010 2016 $5,000,000 8.42% $250,000
Martin St. Louis 37 TBL 4 2011 2015 $5,625,000 8.75% $375,000
Martin Havlat 31 SAN 6 2009 2015 $5,000,000 8.80% $250,000
Brian Gionta 34 MTL 5 2009 2014 $5,000,000 8.80% $250,000
Marian Hossa 34 CHI 12 2009 2021 $5,275,000 9.29% $25,000
Jason Pominville 30 BUF 5 2009 2014 $5,300,000 9.33% $50,000
Shawn Horcoff 34 EDM 6 2009 2015 $5,500,000 9.68% $250,000

Now that we have our control group, let's take a look at the points per game that the players put up in the two seasons prior to signing their new deals as well as their age when they signed the deals (note: the age thing is approximate):

Name PPG Age At Signing
Martin St. Louis 1.18 35
Marian Hossa 0.94 30
Martin Havlat 0.90 27
Jason Pominville 0.89 26
Joffrey Lupul 0.82 29
Shawn Horcoff 0.77 31
Mikhail Grabovski 0.74 28
Shane Doan 0.73 36
Brian Gionta 0.69 29
Ales Hemsky 0.67 28
Tomas Plekanec 0.66 28

Again, Lupul looks good by this metric. His PPG production fits in with the group as does the age at which he signed the deal. Obviously, this is a simplistic measure as it doesn't look at how each player put up the points or whether they will/would continue to be given the same opportunities in the future. The assumption is that at this age, the player is in the current role for which he is being signed so there isn't an expectation that a player that has been given top three or six minutes prior to signing will suddenly stop receiving those opportunities. Or vice versa I guess.

Name PPG Rank Cap Hit Cap Pct 2013-14 Cap Rank
Shawn Horcoff 0.77 6 $5,500,000 9.68% $6,224,240 1
Jason Pominville 0.89 4 $5,300,000 9.33% $5,999,190 2
Marian Hossa 0.94 2 $5,275,000 9.29% $5,973,470 3
Martin Havlat 0.90 3 $5,000,000 8.80% $5,658,400 4
Brian Gionta 0.69 9 $5,000,000 8.80% $5,658,400 5
Martin St. Louis 1.18 1 $5,625,000 8.75% $5,626,250 6
Tomas Plekanec 0.66 11 $5,000,000 8.42% $5,414,060 7
Joffrey Lupul 0.82 5 $5,250,000 8.16% $5,246,880 8
Mikhail Grabovski 0.74 7 $5,500,000 7.83% $5,034,690 9
Shane Doan 0.73 8 $5,300,000 7.55% $4,854,650 10
Ales Hemsky 0.67 10 $5,000,000 7.12% $4,578,160 11

Again, it's simplistic but if you're looking at the market based on boxcar stats then this deal fits in the market. The key is that I think that's a fair assumption of how the market is viewed among the majority of fans and some pundits:

What a shock. So let's agree that while we understand that there are a number of other metrics that can be used to compare this pool of players that by the one that most fans will use it's not that bad of a deal. Of course, once we dig in it may not be as flattering of a comparison but at least this gives a better picture of CapGeek's list of 20 comparable contracts.