According to Friedman, the Leafs and Habs may have gotten into a bit of a bidding war for the services of Ben Chiarot during back in 2019, when the Hamilton, Ontario native was a UFA. As we now know, the Leafs ended up with the short end of the stick.
If true, it's likely that the interest hasn't gone away for the Leafs, and Chiarot certainly checks a lot of boxes for GM Kyle Dubas. He's a big, physical defenseman who plays the right side (though he does shoot left) and he won't break the bank with his $3.5M AAV.
The one concern here is that Chiarot's past two seasons in Montreal has not been particularly great for the 30-year-old. Maybe a change of scenery will do him some good, but if the Leafs do decide to bring him in, the move will not come without some level of risk, as Chiarot is a combined -33 over the past two seasons.
