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Radio Host Proposes Ridiculous Hypothetical Trade That Sees the Leafs Land Sidney Crosby

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Ryan Smitheram
November 26, 2024  (8:22)
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Sidney Crosby scored his 600th career goal over the weekend
Photo credit: Charles LeClaire-Imagn Images

The future of Sidney Crosby is in question with the Pittsburgh Penguins struggling, and OverDrive co-host Jamie McLennan proposed a crazy trade involving Crosby to the Toronto Maple Leafs.

On Monday's edition of TSN's 'OverDrive' Bryan Hayes, Jeff O'Neill and Jamie McLennan discussed the future of Sidney Crosby in Pittsburgh, given the fact that they have been struggling mightily so far this season.

There had been plenty of trade talk surrounding the future hall-of-famer prior him signing a 2-year extension at the start of the season.

While Crosby clearly does not want to go anywhere, teams and the media will continue to ponder the idea of him leaving Pittsburgh, and Hayes and O'Neill admitted on Monday's show that they know it wouldn't happen, but want to see him end his career in Toronto.

When asked to propose a hypothetical trade that may kickstart a potential negotiation for the Cole Harbour, Nova Scotia native, McLennan dove right in.

"Because we're being hypothetical... I'll trade Sidney Crosby and Tristan Jarry for Joseph Woll and Easton Cowan and a first and a second first because of the term on Crosby's contract. It's a package that Tre might hang up the phone and go 'I can't make that happen'."


The consensus among the three was that, immediately, there would be difficulties due to the money involved for not just Crosby, but Jarry as well. Both have multiple years left, and the Leafs would need a massive amount of money retained, obviously increasing the acquisition cost.

While it would be a sight seeing Crosby in a jersey other than the Penguins' black and gold, it is highly unlikely that will happen and the now 37-year-old appears set to ride off into the sunset in Pittsburgh.

Never say never, though.

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Radio Host Proposes Ridiculous Hypothetical Trade That Sees the Leafs Land Sidney Crosby

Will Crosby agree to be traded at some point in the next 3 seasons?

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