The fact that the Oilers have been a lot more successful than the Leafs in the playoffs (but at this point, what team hasn’t?) really doesn’t have anything to do with my point, which is that Holland seems borderline obsessed with Leafs players.
Which is logical. The fact is, there are certain types of players that want to play in Canada and more specifically are willing to play in Western Canada. The reality is that this list is not that big. If you can get players that want to be out here and are also slightly undervalued by their previous team and/or willing to be dropped by said team, then its kind of a no brainer to go for them. Ceci was very valuable for us and is signed to a friendly deal. Same with Hyman.
It's not that Holland is obsessed with Leafs players, it's that the org is targeting players that have shown they can play in a hot Canadian market but also are willing to come to a smaller and less "jewel of NA" city like NY, TOR, VAN, LA, etc. It happens that most of these guys are TOR because of a few reasons:
A) TOR is up against the cap like us and has to stay lean every year so they can't always match the UFA term or prices.
B) Other CAD teams are less competitive so they sell at the deadline and the players don't reach UFA. IE - Copp, Chiarot, Kulak, Toffoli, etc. Even Van is considering moving Miller prior to UFA. When you are trying to make playoff runs you aren't going to sell at the deadline, so you have more players going to UFA by default. No different than Gaudreau about to walk in CGY.
People need stop making it sound like some consipiracy. If TOR was a basement dweller always selling off assets for futures, we very likely wouldn't be signing any UFA because there wouldn't be many of value. Likewise, if you weren't trying to stay thin on your signings and just wanted to retain at any cost, these guys wouldn't be leaving.