One of the most significant issues facing the Maple Leafs for years now is that they have so much money committed to their top 6 forwards (mainly four guys) that they lack the depth and defencemen needed to win when it matters most.
Going into the 2020 NHL season, Kyle Dubas apparently had an offer on the Table from the Florida Panthers to acquire Mackenzie Weegar, who would have been a very welcome and valuable addition to the Toronto Maple Leafs lineup.
At the time, Weegar was not signed yet, but he was an RFA, coming off a one-year contract which paid him $1,600,000; he eventually signed a contract on November 6th that was three years with a $3,250,000 AAV. A cap hit that a Maple Leafs team lacking cap space could afford.
The offer that the Florida Panthers wanted in return for Weegar was Andreas Johnsson and Travis Dermott, but this was too much for Dubas.
Shortly after this trade was turned down, Johnsson was traded to the New Jersey Devils for Joey Anderson (who has played six games for the Maple Leafs).
Dermott, on the other hand, was with the Leafs up until the trade deadline last season when he was traded to the Vancouver Canucks for a round 3 pick in the 2022 draft (Jordan Gustafson).
This is definitely a trade that would have benefited the Maple Leafs, but Dubas did not believe it was a win for the Leafs.
CREDIT: House of Hockey