When do the Blackhawks plan on winning again? It’s hard to tell.

The root of the Blackhawks issues can be tied to draft issues detailed in the first part of our “State of the Franchise” series.

Without success in the draft, the Blackhawks have had to look elsewhere to fill out their rosters, but salary cap limitations hampered their ability to make trades or sign prized free agents. But after several years of cost-cutting measures, Chicago finally had a chance to do something — and did nothing. That’s the short version of the story.

The longer version largely revolves around the eight-year contract extension worth $55 million ($6.875 million annually) given to defenseman Brent Seabrook in September 2015. It was a curious move at the time that continues to look worse as age catches up to the Blackhawks longest-tenured player. It’s been debated and discussed ad nauseam since it occurred, with further analysis no longer necessary.

Since that contract was handed out, the Blackhawks have had to make a series of moves in the name of cost certainty or shedding salary cap space:

• June 2016: Teuvo Teravainen and was traded to the Hurricanes in exchange for a 2016 second-round pick to help unload Bryan Bickell’s contract. Nine days later, Andrew Shaw was traded to the Canadiens for two 2016 second-round draft picks
• June 23, 2017: Niklas Hjalmarsson was traded to the Coyotes for Connor Murphy and Laurent Dauphin. Artemi Panarin was included in a trade with the Columbus Blue Jackets that returned a package including Brandon Saad.
• July 12, 2018: Marian Hossa’s contract was included with a third-round pick, Jordan Oesterle and Vinnie Hinostroza in a deal with Arizona that brought back Marcus Kruger, added prospect MacKenzie Entwistle and a 2019 fifth-round pick that’s since been traded./

In all five trades, salary cap considerations were involved. The Shaw, Bickell/Teravainen and Hossa/Oesterle/Hinostroza trades all helped shed salaries, while the 2017 trades provided the Blackhawks with more cap certainty than the contracts belonging to Hjalmarsson and Panarin.

Those deals provided general manager Stan Bowman with salary cap flexibility he hadn’t enjoyed in years. And what did Bowman do with that cap space? He signed Brandon Manning, Chris Kunitz and Cam Ward. This comes one year after the Blackhawks “big” free agent signings were Lance Bouma, Tommy Wingels, the aforementioned Oesterle and an aging Patrick Sharp.

In recent summers, the Blackhawks have looked like a team with an eye toward the future, less concerned with winning in the present than they are with preparing for the next decade of hockey.

Mixed message

Before the season started, Bowman told the Chicago Tribune that he expected the Blackhawks to make the playoffs. In July 2018, team president and CEO John McDonough told WGN Radio that making the playoffs was as “top priority.” McDonough doubled down on those playoff expectations soon after the firing of head coach Joel Quenneville in November.

John McDonough said he believes this #Blackhawks team is a “playoff team.”

— Madeline Kenney (@madkenney) November 6, 2018

For three offseasons, the Blackhawks shed salaries and shipped out talented players, all for the sake of creating cap space. And then, with room to maneuver in the 2018 offseason, the Blackhawks spent little money and got even less value in return.

Bowman said the Blackhawks wanted to save cap space to re-sign Alex DeBrincat and Nick Schmaltz in the 2019 offseason, yet one of those players fell so far out of favor that he was traded away before December. Chicago received at least one quality player in return (Dylan Strome), but spent an offseason saving money for a purchase they never made.

And that’s the most frustrating part about where the Blackhawks sit right now. For several years, they’ve said they were still in a win-now mode, but were restricted in free agency and the trade market due to a lack of salary cap flexibility. After several cost-cutting moves, however, the Blackhawks finally had the wiggle room to make moves. And they did absolutely nothing with it, while maintaining — at least in public — they still intended to win now.

So which is it?