Toronto and Boston are facing each other in the first round for the second consecutive season. The Bruins eliminated the Maple Leafs last season with a 7-4 win in Game 7 after trailing 4-3 entering the third period.
Tavares quickly became an offseason target for a Toronto, which was disappointed by its early playoff exit. The same could be said for Boston, which was eliminated in five games by the Tampa Bay Lightning in the second round.
Looking back, Tavares said Boston made a compelling case when the two sides met.
"I'd already had a lot of respect and a really good impression of what the Boston Bruins had been for basically a decade and playing against them a lot. You're impressed by the way they work together. How they try to build their hockey team and how they envision having success in both the short and long terms.
"The professionalism, structure and attention to detail goes right through the organization, and you see that trickle down to the type of players they have on the ice that have set the tone for them for a long time. Those are major points."
Cassidy came away from the meeting hoping Tavares had been sold on Boston, but it wasn't to be. In the end, he chose the Maple Leafs, the team he'd grown up rooting for in Oakville, Ontario.
"I like the guy," Cassidy said in a phone interview last week. "He's honest. He got to the points he wanted, the questions he wanted answered. I have a lot of respect for him.
"I don't judge him by the choice he made. He had his choice of teams. Good for him. I found him to come off as a true professional, a good guy, a solid guy. Now the opposition, unfortunately, but a good guy."