The challenge of evaluating each Blackhawks trade on paper

After every trade deadline, there comes a rush to judgment as analysts and fans try to figure out who "won" and "lost" on one of the busiest days of the year. We often try to grade moves in real-time, even while admitting we don't know what happened behind the scenes. It's a fun, and occasionally illuminating, exercise, but it always comes with the known caveat that these deals play over months and years, not the hours after the trigger has been pulled.

I bring that up because of the curious case of Blackhawks general manager Stan Bowman, who is often one of the busiest executives around the NHL at this time of the year. Bowman is, for the most part, a beloved figure in Chicago. The man who has kept the Hawks' dynasty dreams alive and well, Bowman has maneuvered through countless challenging situations to retool the team as a contender each year.

And yet, Bowman seems to lose trades constantly. It's not hard to go back through his track record and find deals that seem curiously lopsided. Nick Leddy for one good prospect? Patrick Sharp and Stephen Johns for basically nothing? Two high draft picks to rent Antoine Vermette and Kimmo Timonen? On paper, you could argue pretty easily that the Hawks "lost" all of these trades, and you'd probably be right.

Still, Bowman is one of the best GMs in the NHL. He's roundly lauded for his ability to keep Chicago among the league's elite year after year. How is it that such a respected, successful GM often seems to be on the losing end of his biggest trades, then proceeds to compete for Stanley Cups?

When it comes to Bowman and Chicago, they're always content to lose the battle if it means winning the war.

The Hawks are in a unique situation, which becomes apparent just about every time Bowman heads to the negotiating table. Chicago has the two highest cap hits in the entire league with Jonathan Toews and Patrick Kane making $10.5 million each. They're totally worth it, but having nearly one-third of your cap space eaten up by two players demands some creativity. It means you can't quite manage your assets and roster in the same way as a team that's structured differently and is on a different timeline. Sometimes it means trading players basically for salary cap space.

That context helps explain why Bowman's recent moves have received widespread praise despite the consensus that he paid an extremely high price. In a vacuum, giving up two very good prospects in Marko Dano and Phillip Danault, a first-round pick and a second-round pick in order to rent Andrew Ladd, Dale Weise and Tomas Fleischmann for four months sounds like a bad idea. Indeed, the Jets and Canadiens were likely thrilled with their returns in those respective trades -- even though the Hawks still came out looking like winners.

"Chicago paid a premium to pull this trade off -- something teams like Florida and Washington weren't willing to do -- but it won't matter if they're raising the Cup in June," said ESPN's Craig Custance in his analysis of the Ladd deal.

And that seems to sum up where the difficulty with evaluating Bowman's moves lies. If the GM overpays a bit in some trades, but the team raises its fourth Stanley Cup in seven seasons, how much does it matter? The risk in having some challenges down the road is always easier to swallow when you're blinded by the excitement of the near future.

But at same time, Bowman isn't bailing on the future, either. This is what makes the Hawks' player development system so valuable. Having a strong farm system allows Bowman to go into these trade talks without worrying that he'll burn the system to the ground. Prospects are valuable because they can turn into good players -- not only themselves, but as assets if they're traded. Dano ultimately never did much for the Hawks on the ice, but he undoubtedly served value to the team by becoming a central part of the Ladd deal.

Even now, the Hawks still have a fairly healthy group of prospects led by Ville Pokka, Ryan Hartman, Nick Schmaltz, Tyler Motte and Gustav Forsling. There are countless other intriguing players whose rights are held by Chicago, too. And in the meantime, thanks to trades afforded by the organization's depth, Chicago is fully committed to defending its Stanley Cup.

When it comes to all these trades and the way we talk about them, it's often nuanced. How this player will fit, how that prospect might develop, whether the deal will ultimately be justified in the future. And yet, everyone seems to agree that the math is a little different when a championship is within reach. As Custance said, "He might not win trades, but all he does is win Stanley Cups."

And really, that's the deal with Bowman's trades. He might "lose" sometimes, but his ability to develop the team's prospect pool and keep a stellar core together allows that to happen regularly without leaving the team's future gutted. It's a remarkable balancing act, one that Bowman doesn't quite get enough credit for when you see folks on Twitter giving him a hard time for the Sharp deal. You just can't analyze his deals without considering the salary cap implications and how the moves allow the team to keep players like Toews, Kane and Keith.

The Hawks might not win every trade they make, but they're the Stanley Cup favorite with several top young players and a decent farm system still intact. Ultimately, what else can you ask for?