As much as Benn's acquisition improves the depth on the Jets blue line, it also shows the level of confidence Cheveldayoff has in young defencemen in the organization - like Dylan Samberg and Ville Heinola.
The 20-year-old Heinola was reassigned from the Manitoba Moose to the Jets taxi squad on Mar. 17, just as the Jets were starting a season-long seven-game road trip.
He hasn't played a game since but had 10 points in 16 games with the Manitoba Moose this season.
"I think Ville, he's been a little bit of a victim of circumstances here with respect to the taxi squad being up here," said Cheveldayoff. "We think Ville can step right in and play when the opportunity presents itself. We think Ville will have a very short learning curve in that he stepped right in last year, even with less experience, and proved that he can step in. He's that much stronger, that much more a pro."
Logan Stanley is another player on the back end who has taken big strides this season.
The 2016 first-round pick played his first NHL game on Jan. 18 against the Toronto Maple Leafs, the scored his first NHL goal on Mar. 27 against the Calgary Flames.
Stanley averages 12:46 per night and his +12 rating leads all NHL rookies this season.
"The interesting thing is that we're at a point in time, we're 40 games in, which generally is the halfway point of a season where young players like (Stanley) are only just finding their way and continuing to get better and better," said Cheveldayoff. "So, I look at the opportunity that's in front of this group to continue to reap the benefits of some of the younger players getting better and getting an opportunity that should be beneficial to us moving forward."
Winnipeg is 16 points above the playoff line and sits second in the North Division with 15 games left on the schedule.
As much as they'd like to give players like Heinola and Samberg a look, they're also limited to what the collective bargaining agreement allows them to do - specifically, the four-recall rule.
"The four-recall-rule is something that, again, once you use that recall then that player basically has to stay," said Cheveldayoff. "So, again, we'd like to get all our players playing some sort of games here at some point in time. That's a priority, whether that's guys eligible to play in the American League, we'd like to get them playing some games, or if it's giving some opportunities to some players in the National Hockey League."
With the deadline behind him and the team, the focus is now squarely on the battle for positions in the North.
"Obviously, a lot of teams did some other things, but for yourself you look at what's available in front of you, what fits and you make those moves accordingly," said Cheveldayoff. "I think we've sent the message that we've added some depth that can help us as we move forward here in the remaining games and into the playoffs."