Did the Jets Wait too Long on Connor Hellebuyck?

There's something about the Connor Hellebuyck situation in Winnipeg that feels a little backwards. Usually, when a star player asks for a trade, the pressure is on the team to find the best possible deal. But there is another kind of pressure that shows up when a trade doesn't happen. Time.
Time may not be helping the Jets deal with the Hellebuyck situation.
Hellebuyck has asked out. He's got a full no-movement clause, but apparently there are teams he'd be willing to go to. So, on the surface, Winnipeg should have some options. The problem is that the NHL has kept moving while the Jets have been trying to figure out what those options are.
Florida may have been interested, but the Panthers just spent a bunch of their trade capital acquiring Brady Tkachuk. Buffalo apparently talked to Winnipeg before the draft, but the Jets wanted the fourth overall pick while keeping their own first-rounder. The Sabres weren't interested. And then there are the little things that can make a trade even more complicated.
Some no-trade clauses changed on July 1. Suddenly, players who might have been available to Winnipeg earlier in the summer had a little more say in where they would go. That's how a trade that looked possible in June can suddenly look a whole lot harder in September. And here's the part that really interests me.
Related: Connor Hellebuyck and the Complicated Meaning of Loyalty
The longer the Hellebuyck situation goes on, the less leverage Winnipeg may have.
It's not that the Jets have no leverage. Hellebuyck is still an outstanding goaltender, and somebody looking for a No. 1 goalie should be willing to pay for one. But every potential trade partner knows the situation. They know Hellebuyck wants out. They know Winnipeg eventually has to make a decision. And they know training camp is coming.
That's not exactly the recipe for maximizing a return. It also puts the Jets in a rather awkward position. If they can't get the package they want, do they simply keep Hellebuyck and start the season with everybody knowing he'd rather be somewhere else?
That's not a particularly comfortable way to begin a season.
Will the Jets get any kind of return for their Vezina-winning goalie?
Maybe Winnipeg eventually gets the kind of return it wants. There are still teams that could become interested, and goaltending situations can change quickly. But the interesting thing about this situation isn't really which team eventually gets Hellebuyck.
It's whether Winnipeg missed its best opportunity to move him. Sometimes in hockey, the hardest part of making a trade isn't finding a willing buyer. It's recognizing when the market is at its best. The Jets may be finding that out right now.
Related: What Is the Jets' Connor Hellebuyck Really Thinking?
