Quoting: RowdyRoddy96
2019 he was in trade rumours with the Edmonton Oilers
2020 he was in trade rumours with about half the league due to his looming contract situation
2021 he was injured if he wasn't he would have been dealt
First Leblanc took that deal with a hand shake that the following year he would be taken care of, Toronto does not have the cap space to make this kind of deal and handshake deal.
Next, rumors are just that rumors. Like the rumors that Stamkos was going to sign in Toronto when his contract was up several years ago. Friedman stated that anyone on the team was available, minus Larkin and Sieder. Does not mean anyone was going to be dealt but Yzerman would listen, not actively search for a deal.
Based on Yzetman's tra k record if Bertuzzi were to be dealt it would not be for a player who is on the verge of free agency. He is very shrewd GM and would wait until he gets a deal he likes and this is not the deal I beleive he would like. Reilly is a very good player, no doubt, but signing Bertuzzi would and will be easier to sign than a pending player who could walk and leave Yzerman with nothing.
By the way, this rumors that you speak of, could you please produce them or show where I can find them, because I have never heard of this Oulers trade. Just asking.