After having a down year, DeBrusk's future in Boston has been in question, many even thought he was going to be traded at this years deadline, but the Bruins decided to keep him around for the playoffs, and now they might be losing him for nothing.
At the end of the year during the Bruins locker room clear out, Jake DeBrusk expressed how he was frustrated that there wasn't a deal in place for him and how he played the whole year without an extension.
During the end of year press conference Don Sweeney stated the Bruins took an aggressive approach with DeBrusk. Chances are that the Bruins did offer him a contract, but it might not be what he wants.
If Jake DeBrusk does sign with the Leafs in the off-season, the Bruins would have lost two fan favourites in back-to-back years, last year being Tyler Bertuzzi.