And the decision-makers at the Saddledome are all too aware that the gamble didn’t pay off. What might the team’s cupboard of prospects look like if the organization had acted earlier and shipped him out of town in exchange for young assets?

But with the Flames facing off against the Blue Jackets on Friday night in Ohio, you can’t help but think about it, right? Especially when the Flames currently have four key players on their active roster who are set to be unrestricted free agents next season.

That’s a list that is headlined by first-line center Elias Lindholm and big-minute defenseman Noah Hanifin, as well as blue-liners Chris Tanev and Nikita Zadorov.

The Flames are being patient, but in Gaudreau, there’s an easy-to-see reminder that patience can only take you so far.

There comes a point where, if a player hasn’t put pen to paper, you can’t risk losing them for nothing.
That’s a lesson Craig Conroy spoke about on the day he was introduced as the Flames general manager.

“I was hoping Johnny was going to come back. I thought Johnny was going to come back, but I don’t think I would let that happen again,” Conroy said. “I told Flames president of hockey operations Don Maloney in the meeting that I truly thought John was going to come back and when he didn’t, it was disappointing, It came right down to the last minute but then you think, ‘Uh-oh, you just lost your best asset, one of your best players of all-time and you didn’t get anything for him.’

“It was a real eye-opener for me. I sat in my office for a while, and I shut my door.”

As the Flames try to chart a course forward with their potential free agents, it is worth revisiting the way everything played out with Gaudreau.

They chose not to sell high. They chose not to sell at all.

Craig Conroy: ‘You don’t want guys to walk for nothing’

If there was a right time to trade their star winger, it likely would have been the summer before the 2021–22 season. He had a modified no-trade clause that kicked in toward the end of July and was coming off a bit of a down year, but there’s no doubt there would have been suitors. The Flames chose to hold on, just like they did with the likes of Lindholm and Hanifin this summer.

Of course, Gaudreau had signaled publicly that he was willing to resign long-term and stay in Calgary. The Flames had every reason to feel like they had a real shot at locking him up long-term—again, their current group of pending UFAs has sent similar signals.

But as they learned, saying publicly that you’re willing to stay is not the same as actually committing to it for real. It’s the second part that actually matters.

And in the end, Gaudreau decided the grass was greener in Columbus, of all places.

Should they have traded him during the 2021-22 season? It’s easy to make that argument, but it would have been incredibly difficult to sell the fanbase on dealing away the team’s best player during a season in which they really did look like Stanley Cup contenders and would go on to win their first playoff series in over 15 years.

What happens this year, then, if the Flames are sitting pretty in the standings as the trade deadline approaches?

Are they willing to make the same gamble they made with Gaudreau and risk losing guys like Lindholm and Hanifin for free?