Elliotte Friedman Hints at When a Sidney Crosby Trade Could Happen, and What It Will Cost

On '32 Thoughts' Elliotte Friedman says that a deal for Sidney Crosby, if it were to happen, would likely take place after the Olympics, pending on where the Pittsburgh Penguins are in the standings.

Friedman states that a trade for Crosby isn't guaranteed, but as the season goes on and Pittsburgh isn't winning, that could give course for things to change, and could open up the possibility of a deal done nearing the trade deadline.

Why the Timeline for a Crosby Trade Matters More Than Ever

Elliotte Friedman's new reporting gives a clear indication as to when a Sidney Crosby trade may happen, and how, but still has one key factor to happen, and that's Crosby's decision on his future.

Even with three Stanley Cups, Friedman says that Crosby is still focused on winning and his goal is to be on a winning roster.

Friedman says that while Crosby isn't planning on leaving, his focus is on being on a team that will win. He adds that while Crosby could leave Pittsburgh, they'd have to be in the basement for a deal to be possible.

Ultimately, as Friedman points out, the deal is reliant on Crosby wanting to leave, and as one of the league's greats, it's Crosby who will dictate his next move rather than Pittsburgh, putting the cards in his favor.

Elliotte Friedman makes clear that whatever the return for Sidney Crosby, it's going to be a costly one.

Some may be hesitant at paying top price for a top prospect and a high draft pick just to start a deal for a 38-year-old Crosby, but he's still one of the league's most productive players regardless of his age and capable of being a PPG forward who is a proven winner, the cost will still be heavy.

The rebuilding Penguins will be looking to get top dollar and quickly add to their retool, getting youth adds that will help the team in the long-term for a player who will be retired by the time the next Penguins contention window opens.

Crosby was coy when asked about playing for his boyhood Montreal Canadiens, with Friedman addressing that the Habs could be a suitor, but they'd have to make a move involving assets, which they'd not want to do unless they knew for sure they'd be able to acquire Crosby.

A team like Montreal will be unlikely to want to move players such as Ivan Demidov and Lane Hutson, and both are likely out of the question. The second tier of prospects such as David Reinbacher and Michael Hage may be more of a headline return.

For Toronto, they don't have top prospects except for Easton Cowan, and a deal involving Ben Danford and a 2028 first, the earliest first rounder the Leafs have, although they could acquire a pick earlier, Pittsburgh, in their rebuilding stage would rather get assets sooner rather than later.

This could be what ultimately takes Toronto out of contention for Sidney Crosby, meaning it would likely take a very appealing deal to acquire the future Hall of Famer, one the Leafs would have to make hard choices to see come to fruition.