The Winnipeg Jets’ General Manager Kevin Cheveldayoff has some big decisions up ahead. The Jets currently sit tied for second last in the Western Conference and last in the Central Division. They had two huge pending free agents between Andrew Ladd and Dustin Byfuglien (since reduced to one with Byfuglien extended), while they also have a major part of their future looking for raises with Mark Scheifele and Jacob Trouba.

Well, we’ve decided to help out Chevy make some of these decisions with a series of investigations on the Jets. We’ll take a look on where the Jets are and where they could be.

We started our series with a breakdown on how the Jets’ roster compares against playoff teams. We noted that the Jets have a lot of top pieces but haven’t built the best supporting cast. Then we looked where the Jets’ weaknesses are impacting them and where they need to improve.

When you look at the Jets’ roster, you may notice there is a bit of a split. There is essentially two separate cores: one of the Jets young and homegrown players, and the older core predominately consisting of former Atlanta Thrashers. There are a few players in the middle but most are either above 27 or below 23 years of age.

The Jets forwards Mathieu Perreault (28), Bryan Little (28), Blake Wheeler (29), Drew Stafford (30), Andrew Ladd (30), Chris Thorburn (32) all sit at 28-years of age or older. The backend adds Dustin Byfuglien (30), Toby Enstrom (31), Mark Stuart (31), and Adam Pardy (31) to the list, plus Ondrej Pavelec (28) in net.

Meanwhile the Jets carry Joel Armia (22), Mark Scheifele (22), Adam Lowry (22), Connor Hellebuyck (22), Jacob Trouba (21), Andrew Copp (21), Joshua Morrissey (20), Nicolas Petan (20), and Nikolaj Ehlers (19) all below 23 and still reside on their ELC.

It’s not too difficult to see what is likely Cheveldayoff’s line of thinking.

The term remaining on many of the Jets’ older players plus the recent Byfuglien contract extension indicates management still hopes to contend with the bulk of their older core intact. The younger core will then be used to support the older core as cost controlled depth options to make up for the value lost with more expensive players.

Time is limited though. Eventually Jets’ young core will deserve significant raises, as we may be seeing already with Scheifele and Trouba. The older core will cost too much and will have to be reduced to just a few pieces in more of a veteran leadership role, as the torch is handed off to the next group.

The combination of all these factors seems to create a tight window for the Jets. We can illustrate this looking at the Jets’ contracts as pulled from NHL Numbers:

Ironically the Jets optimal window seems to overlap the inflated predictions made by a mainstream media outlet not long ago. While it may have been a bit presumptuous for The Hockey News to predict the Stanley Cup, it should be the Jets’ goal given the pieces they control.

The Jets’ will likely still cary players like Wheeler, Little, Enstrom, Myers, Byfuglien, plus any other individuals signed to their own extensions. The older players in the Jets younger core, like Scheifele and Trouba, will be entering their peak performance age. The troops will also be reinforced with top prospects like Josh Morrissey, Nic Petan, Kyle Connor, Eric Comrie and others.

When Chevy makes his choices impacting the team’s future, hopefully he will take all these factors into account. Although, in this case, we’re more building a foundation of knowledge for the next few pieces of the series.