Thankfully the core is already signed as he is AWFUL at negotiating. (handed out the worst contracts in the league while Leafs GM)
Not trying to absolve him of the core 4 contracts, but I think remembering the context there is useful. He played hardball with Nylander, which (despite some people's thinking at the time) turned out to be a very good contract. Winning that battle probably lost him the war though, because Nylander sitting out half the season really turned the heat up on him getting the Matthews and Marner deals done (and as people have noted, the Toronto market can be pretty vicious). He caved a little on them there (Marner more than Matthews, as I think Matthews' AAV would have been fine for an 8 year deal), but he probably thought he could get away with it expecting the cap to keep going up pre-COVID. Lesson learned. As for Tavares, you're going to overpay for UFAs, especially stars. The only way to win is not to play. Does that all bode poorly for him if he comes here? Time will tell.