You’ve got to be sure.

Whether the question is, “Is Jacob Trouba a top-pairing defenceman?” Or, “Can I win a Stanley Cup with Sean Monahan as my first-line centre?” an NHL general manager has to absolutely sure he knows the answer before he starts handing out long-term deals to young, restricted free agents on just their second contract.

That is where the Jets are with their unsigned 22-year-old right-shot defenceman Trouba, a player on whom the hockey world is split. He is big (6-foot-3, 202 lbs.), mobile and shoots the puck well. But the question persists when you talk to people around the National Hockey League:

Is Trouba destined to be a top pairing defenceman on a good team? That’s the projection the Jets are facing, as Trouba’s camp is likely asking to be paid and played like a top-pairing defenceman.

Averaging eight goals and 24 points per season over his first three campaigns, the scoring numbers don’t add up to a top-pairing guy. And as one NHL exec asked, “Does Trouba make his teammates better?”

Dustin Byfuglien makes his teammates better, but there is no on-ice similarities that would suggest Trouba’s next contract should be anything remotely close to the $7.6 million that Byfuglien makes. And the Jets already have a defenceman who was over-valued by a previous team — Tyler Myers, who is making $5.5 million despite a sometimes questionable defensive game and average offensive output (27 points last season).

You can’t afford two contract mistakes on one blue line, and that’s why Jets GM Kevin Cheveldayoff doesn’t appear to want to unload any Brinks trucks at Trouba’s doorstep just yet. He was sure on Mark Scheifele, and signed him to an eight-year, $49 million deal, proving that the Jets will spend it when they find the right target.

We spoke with Trouba’s agent, Kurt Overhardt, on Thursday morning. He politely declined to shed any information on the topic, stating that he and Cheveldayoff have managed to keep negotiations out of the media thus far, and he is trying to keep it that way. Cheveldayoff is notoriously quiet regarding situations like these.

But the Jets only have to look westward to see the effects of having given big money to players who weren’t fully proven to be wary.

Calgary signed defenceman Dougie Hamilton to a six-year, US $34.5 million deal upon his second contract. For the first half of last season Hamilton was a train wreck defensively, and even though he went 12-31-43 offensively, the questions still exist about Hamilton’s overall game.

In Edmonton the Oilers went long-term on Taylor Hall, Ryan Nugent-Hopkins and Jordan Eberle upon their second contracts, paying them each $6 million over six- or seven-year terms. Hall, since traded, has produced at a level commensurate with his salary, while Eberle has been a 64-point player when healthy.

Nugent-Hopkins, however has not come close to returning value. At the time of the signing, then-Oilers GM Craig MacTavish thought he was getting a good deal on a future first-line centre. But with Connor McDavid and Leon Draisaitl now in the fold, it is quite possible that Nugent-Hopkins could become the third best centre in Edmonton’s lineup, at $6 million per season.

Let’s go back to Calgary, where Flames GM Brad Treliving is fighting the same battle with his unsigned RFA’s Monahan and Johnny Gaudreau. Their agents see the Flames first-line centre and left-winger, and likely want long-term deals that will pay them as such.

I like Monahan’s game a lot, but does he fit into the group with Connor McDavid and Jack Eichel — two sure-fire superstars that we know will still be top line players if their teams are of a Stanley Cup caliber? Or will Sam Bennett turn out to be a better player than Monahan one day?

Will Monahan fit into that category of player that, if he’s your second-line centre your team is fantastic, but if he’s your first-line centre it might not be enough? I’m not sure anyone knows the definitive answer to that yet.

Then there is Gaudreau, who had only 22 of his 78 points last season in road games. He’s a fantastic player, but does he have the leg strength and speed to be as good as Patrick Kane, one of the very few players of a similar size to become an NHL superstar?

Or do those road stats suggest that, with the proper matchups, Gaudreau can be contained? You can fall on either side of that fence, but the point is, if I am a GM handing out long-term dollars to Gaudreau, I want to be dead certain in my own mind that the player is what I am paying him to be.

In the end however, Trouba, Monahan and Gaudreau have two options: Negotiate a shorter term contract they can live with and have a dynamite season next year, or hold out. And in our experience in this department, players always lose in the hold out game. (See: Jonathan Drouin, Tampa).