Flames Pass.

GM Craig Conroy would be immediately fired if he passed. Let's see: 33/34 year old Chris Tanev for 1 season, 34 year old Mikael Backlund for 1 season, and an undersized middle-six forward all for a top-10 40 goal scoring winger that comes with an 8 year extension. If those players were Leafs, other fans would say it costs the first just to dump those contracts. And ironically enough, given the Leafs cap situation, it probably would.

all that for one year of Nylander

Nine years

While I think the trade is fair, I'm not sure the Flames would accept. I don't think adding Nylander makes them much better this year with the hole that Tanev leaves behind and the lack of forward depth the team has to make up for in losing Backlund and Dube. Additionally the Flames would have no chance of retaining their UFAs since Nylander's extension would pretty much eat any bump in the salary cap.

There's no way losing Tanev would cripple that defence. After trading him you guys are still left with one of the best top-4s in the league: Hanifin-Andersson and Kylington/Zadorov - Weegar. As for the forwards, I'm kind of surprised how little confidence you have in your younger players like Pelletier and Coronato, unless you're talking about the depth after them, but in that case I'm not sure what "lack of forward depth" means. You guys also make up for the forward depth by adding a needed star producer in your lineup for 9 years. Plus you'll still be able to afford Hanifin and Lindholm after so idek what you're talking about.

The only reason the flames would want Nylander is if Lindholm is staying. If he does stay, then Calgary is paying him roughly 8.75MM AAV, plus Nylander's 9.25MM AAV next year with a 4MM cap increase. That leaves $17,450,000 to fill 10 roster spots. Assuming Pelletier, Dube, Kylington, Zadorov and Wolf continue their trajectories, they all need raises, which will be over the average 1.745MM for each roster spot left. Thus, they'd be filling next year's roster with ELCs. Also that Florida pick is conditional and tied to the trade they made with Montreal to dump Monahan's contract. It costs them an additional 4th if they trade it and removes the protection they have by allowing Montreal to take Florida's pick. So trading that pick exposes them to losing a high draft pick in 2025 (assuming they continue to suck).

For this year, Calgary would only have 2.324MM in cap space left to find two bottom 6 centers, a top 4 RD, and a replacement for Hanifin. Assuming they can actually get a decent return for Hanfin, some of it would need to be allocated to fill the holes in the roster.

So no, Connie wouldn't be a fool to reject the deal. For what it's worth, I do think Backlund and Tanev would push the leaf's over the top. They are two of the best shut down players in the league.

Not that this is relevant to the discussion, but if Backlund and Tanev were really guys that could "push a team over the top", then why has Calgary won 2 playoff series in the past decade (1 since Tanev joined)? And on top of that we're trading our 3rd best player in exchange for them. We already have TJ Brodie, who was literally the BEST shutdown defenceman last year based on just about every WAR models.

Because Calgary has no Elite talent on their team. I said that they could push a contending team over the top. The only Elite players we have had on our roster are Gudreau and Tkatchuk, and they both left. Lindholm is a great 2C, but not an Elite Center like Matthews or Mckinnon.

Also, Brodie and Tanev had near identical GSVAs of 1.3

Backlund had a 2.4 GSVA, which is better than everyone on Toronto except your core 4 (which makes sense given their offensive outputs). His defensive component of his GSVA was higher though than all the forwards on Toronto. Brodie and Giordano had the highest defensive ratings for GSVA on the team (19.6 and 18.4 respectively)

Tanev isn't resigning and Backlund won't commit. So if Willie has committed to signing, the flames easily win the trade. Don't see the leafs wanting another small forward in Dube, they are looking for playoff style guys to support the top guys.