The Jets, and the Challenges of a Small-Market Team in the Salary Cap Era

This story originally appeared on VICE Sports Canada.

Kevin Cheveldayoff has seen it happen before. NHL general managers can struggle almost daily with the limitations of the league's salary cap. It can be a balancing act—one moment you have all the cap space needed to run a contending team, and the next you're moving quality players just to sneak under that number set out by the league.

The lessons came hard and fast for Cheveldayoff, the Winnipeg Jets' general manager. In the span of a year, while working as assistant GM of the Chicago Blackhawks, he won a Stanley Cup and then saw Dustin Byfuglien, Andrew Ladd and Kris Versteeg, among others, shipped out as a means to get under the cap. Now Cheveldayoff's Jets could be in for a similar plight come the end of this season.

Cheveldayoff credits his time with the Blackhawks, who have won three of the last six Stanley Cups, as having an influence on his understanding of the cap. The Hawks were forced to trade players like Byfuglien just over two weeks removed from their Cup win in a deal Chicago GM Stan Bowman then said was "simply a salary cap move."

"In that unique situation, and they've had similar situations since, when you win a championship you feel good about making the decision that you did," says Cheveldayoff.

The situation the Jets find themselves in is strangely ironic considering it was Byfuglien and Ladd whom the Blackhawks could not afford to keep, and now it is Cheveldayoff seeking to manage his own salary cap and the futures of those players as well. "Every decision you make today has a ripple effect for many, many years to come," he says.

Winnipeg is laden with rookies and others still on entry-level deals, including Nikolaj Ehlers, Mark Scheifele and Jacob Trouba. But as the salary cap limits not only the flexibility teams have to sign and trade for desired players, so, too, does it often limit the window teams have to win.

The NHL is a cyclical league, largely dependent on cap space and age of core players in their prime. Teams rarely contend consistently for more than a few years at a time (with notable exceptions of course) and often, when up against the cap, are forced to go for it. In a roundabout way, that's exactly what the young Jets are doing: going for it, probably before they should, but because they have to.

"There's not this magic date or time that you can pick and say 'This is when it's going to fall into place,'" Cheveldayoff says.

The nervous energy that surrounds the Jets this season is symptomatic of the the larger issues that teams with emerging young cores face. As the league gets faster and younger, the windows to win are in turn getting smaller.

Getting a steal on a young rookie like Ehlers in terms of point production (he's one of eight Jets players with a double-digit point total) can be a great surprise, but the leverage given to that player when negotiating future deals can be immeasurable. Teams have to ask hard questions about which young players to invest in and for how long.

"The future creeps up very quickly," says Cheveldayoff, noting that entry-level deals for Scheifele, Trouba, Adam Lowry and Michael Hutchinson will all expire at the end of this season.

"There is never a day in the mind of a general manager in the National Hockey League when the salary cap and the short-term, medium-term and long-term future of where things are at isn't very topical."

Ladd, the team captain who notched a career-high 62 points last season, and Byfuglien, the all-around juggernaut defenceman, are set to become unrestricted free agents.

Ladd, 29, is among the top 30 scorers over the past four seasons with point totals similar to Thomas Vanek, who has an average annual value of $6.5 million. Only four defenceman, meanwhile, have scored more points than the 30-year-old Byfuglien over that same stretch. The physical element he brings to his game could see him fetch more than $7 million per season.

Both would represent key pieces to build around, but the expensive contracts they'll require could be out of Winnipeg's price range, a team that has the lowest cap hit in the NHL, according to General Fanager, at $59,895,830 million.

The Jets, however, can still grow with a roster that's loaded with youth, even if the team loses a pair of its top players. And while the Jets have the two, they can go against the script and try to win.

The emergence of Ehlers, and Scheifele solidifying himself as a bonafide two-way centre in the NHL, have helped the Jets excel quicker than many believed. You can of course point to the insanely productive season that their top line of Ladd, Bryan Little and Blake Wheeler is having, but the secondary scoring and overall depth the young players have been providing can't be understated. The average age of the team, fifth youngest in the league, benefits both the club's Cup chances in the future and its cap situation in the present.

With Ehlers in the lineup and producing, Cheveldayoff has redeemed himself in the eyes of some of the Jets faithful who weren't growing impatient at the team's lack of success—although the club is still is search of its first playoff win in its fifth season back in Winnipeg—but instead by the perceived delaying of young players' transitions to the big club.

"Sports fans are impatient. Hey, I'm as impatient as all of them. We live it each and every day," he says. "You want to win right now. But the reality is that there are no shortcuts in this game. It's a process.

"In this industry and in this business, slowing the process down can you help reap benefits and reap rewards."

A talented group and a threat in the Western Conference, the Jets weren't supposed to make any noise this season. Inconsistent play has the team sitting sixth in the Central and three points out of a playoff spot, but they're hanging tough in a dogfight of a division.

From the outside, some would consider the struggles a man like Cheveldayoff faces to be good problems to have. His team is young, its competing, and the organization is paying players less than almost any other in the league (their total salaries are third lowest in the NHL). By season's end, however, things could look a lot different for the team.