BenFred: Painful trade of Blues captain Ryan O’Reilly can pay dividends if GM shortens reboot

Carrying red plastic cups while covered in colorful beads, the Mardis Gras goers who buzzed their way through downtown St. Louis on Saturday morning stirred up some fond memories of the energy that hummed through the streets during the Blues’ 2019 Stanley Cup championship parade.

The vibe inside the Enterprise Center media room presented a stark and somber contrast.

The Captain had left the building.

“He took me on a hell of a ride,” Blues general manager Doug Armstrong said. “And I enjoyed every second of it. But this is the business I chose to be in.”

Armstrong knows how the Ryan O’Reilly trade looks to the non-realists who did not see it coming.

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The longtime executive who has developed over the years a reputation of a cold-blooded and calculated decision maker swapped his beloved captain two weeks before the March 3 trade deadline, while the Blues were riding a three-game winning streak entering an afternoon game against Colorado. The deal finalized the same day O’Reilly had joined Armstrong to participate in a Make-A-Wish event with a young Blues fan. Ouch.

But here’s the truth.

Entering what has become a disappointing season — it’s OK to give the players some of the blame, too — Armstrong was prepared for his reputation to swing the other way. He was ready to be tabbed a sentimentalist, one who did not properly prioritize the future before a wave of pending free agents departed with little to show for it since the pandemic scrambled what was shaping up to be a fascinating championship defense.

Doug Armstrong (copy)

Blues general manager Doug Armstrong addresses the press on Wednesday, June 26, 2019, at Enterprise Center. 

“I was hoping to be here and celebrate a Stanley Cup, but I was also prepared to be here and lose in the first or second round, and be getting drilled by, well, now you’ve lost, and you have no future assets, and you’ve done all this stuff, and you’re an idiot,” Armstrong admitted. “I was hoping to have to be labeled like that, as a guy who didn’t maximize his assets. I guarantee I’m still going to be an idiot in a lot of people’s eyes, but it wasn’t that difficult to move on, because we are not a competitive team with the good teams right now.”

No lies detected, when you remember the Blues’ projected chances of making the playoffs even after their latest tease are below 10%, and their chances of doing real damage even if they snuck in were, let’s face it, zero.

This group’s window snapped shut faster than Armstrong figured, and while he knew it was trending toward closing, he underestimated how obvious the need to retool would become so soon. He tried to thread a needle, and he missed. If he was going to try to get one more strong season from the remaining core, he should have made the core stronger by not letting an important roster piece like David Perron walk into free agency this past offseason, should have waited a bit on rewarding younger players like Robert Thomas and Jordan Kyrou in front of more established veterans whose futures were hanging in the balance, should have sent Tarasenko out even sooner than he did. Maybe he should have found the money for Alex Pietrangelo at the expense of others?

It’s all quite clear now, isn’t it? It wasn’t so easy at the time. And it isn’t easy now, sending off O’Reilly to the Maple Leafs after he’s meant so much to this city, this team, these fans.

St. Louis Blues play against Chicago Blackhawks

Blues forward Ryan O’Reilly prepares for a faceoff during the third period of a game against the Blackhawks at Enterprise Center on Thursday, Dec. 29, 2022.

Hard stuff. But necessary now. Required.

O’Reilly helped carry the Blues to their first ever Stanley Cup championship on cracked ribs. Never, ever forget it. He arrived here as a player whose love of the game had been questioned in Buffalo. He departed as a leader whose inspired play and dedication to the team made diehards and novices alike love Blues hockey more.

Who knows, maybe there is a chance O’Reilly and the Blues can strike a team-friendly deal if his free-agent market is worse than expected, but that wouldn’t exactly mesh with the transition Armstrong has now prioritized. O’Reilly has had a tough age-31 season that he can hopefully reenergize in the right role with the Cup-hungry Leafs. But the Blues are looking to get younger, turning the spotlight toward developing prospects and supplementing the roster with pieces in similar age ranges. The coming days and months but hopefully not years, plural, will be about patience on the ice and moves off it that shorten the wait until a new window is forced open. Slowing the ripping off of the Band-Aid won’t help. It will make transition take longer and hurt worse.

After the late-night trade Friday of O’Reilly and Noel Acciari to Toronto netted the Blues a first- and third-round pick in 2023, a second-round pick in 2024, plus two AHL forwards, Armstrong now holds three first-round draft picks for 2023 and one for 2024, with more potential rentals to flip in pending free agents Ivan Barbashev and Thomas Greiss. These moves won’t help the salary-cap crunch for next season as they are maximizing returns for contracts that were expiring, but Armstrong will leave no stone unturned as he becomes clearer and more pointed about his direction. He still has to solve a disappointing logjam of underperforming defensemen, for example. The word he used multiple times Saturday was “retrenching” and he’s going to do it around the Thomas-Kyrou duo the team already invested in heavily.

Time for those two forwards to lead. Time for Brayden Schenn to prove he’s the next captain. Time for the young guys who were hungry for opportunities to make cases they are ahead of schedule. Time for Craig Berube to prove he is the right coach for this rebuild by not letting effort and energy slip on the ice. Time for Armstrong to maximize a position he has rarely found himself facing. He wants an LA-style rebuild, not a marathon five to seven-year one.

“The equity in the NHL is to have first-round picks,” Armstrong said. “I wish I had a crystal ball where I can tell everyone how this is going to work out, but I don’t. We could use all of those picks to select players. … Or, they might be gone before their names are ever called. I don’t know how it’s going to play itself out. One thing I do know we are going to do is, if we move picks, players, it’s not going to be for one-year players. We need to retrench with players 25, 26 and under that have term on their contracts, so they can grow with that next core we have.”

This part hurts. Armstrong won’t flinch. The architect of the Blues’ last “hell of a ride” created a parade that made Mardis Gras look like child’s play. He deserves a chance to do it again, and he’s not going to waste precious time.

Sports columnists Ben Frederickson and Jeff Gordon take a break from pondering who could be traded next and when, and turn their attention toward a veteran Blues leader who is performing like you would hope a potential future captain would.

Ben Frederickson

Jeff Gordon

Gary Hairlson