Schenn is signed through 2028 at a $6.5 million cap hit and is the captain of the St. Louis Blues.
While his 11 goals and 30 points in 54 games show he still contributes offensively for his team, acquiring him would require some move on the Leafs side.
The Leafs have only $2.2 million in available cap space which is meaning they'd need to cut at least $4.5 million to make room.
One scenario involves the Blues retaining 25% of Schenn's salary, with a third team retaining an additional 25% by reducing his cap hit to $3.25 million.
In this case, trading Max Domi or a package like David Kampf and Nick Robertson could balance the books and make it work.
But the bigger challenge is in the asking price since St. Louis reportedly demands a big return that will likely involve Toronto's 2026 first-round pick and a top prospect.
While the Leafs doesn't want to move Easton Cowan, other prospects like Fraser Minten, Nikita Grebenkin or Topi Niemela could be on the table.
St. Louis also has a need for right-handed defensemen which could make Ben Danford or Niemela attractive trade options.
A proposed trade might see Toronto sending David Kampf, Robertson, Niemela and a first-round pick in exchange for Brayden Schenn with salary retention and Matthew Kessel.
While Schenn's veteran presence could help in a playoff push, his age, contract and the high cost in young talent make this a risky move and the Leafs must decide if his impact outweighs the potential long-term loss.