The Bruins coach knew the players who were returning, the skill on their top line, and the continuing development and maturity of players like forward David Pastrnak and defenseman Charlie McAvoy.
But there were concerns, too, regarding new players, including a new goalie tandem, an uneven schedule, and all the unknowns and unknowables that comes with a new season.
Now, though, he knows.
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"I felt we were a contender] because we had returning players that I knew were capable of carrying this team a long way," Cassidy said. "We'd been in the playoffs, what, five straight years? And a lot of those guys were returning. So are you a favorite versus a contender? That, to me, would have been the question mark with so many new faces.
"Yes, I did feel we were a contender. Were we a top-tier contender? Until we saw some of the new players, how they fit, that would have been a tough question to answer. … Now I do [know
and three NHL Draft picks, including a first-round selection in the 2022 NHL Draft. The Bruins signed Lindholm the next day to an eight-year, $52 million contract ($6.5 million average annual value).
Lindholm had an assist in his first game with the Bruins, a 3-2 win against the Lightning on Thursday, a victory that multiple players acknowledged was a confidence booster.
At the same time, they're remaining realistic.
"With the way that we've been playing the last little while and the guys that we just brought in at the deadline, I think that we do have the potential to make a good run [in the playoffs]," forward Brad Marchand said. "But you look at the teams in the East, every playoff team is a legit contender this year."
Part of the reason the Bruins have been so good recently dates to a decision made by Cassidy to break up the top line of Marchand, Patrice Bergeron and Pastrnak, a move he's made in the past to varying degrees of success. This time, it's worked.
It extended the lineup, creating three scoring lines that became even better when Jake DeBrusk moved to the top line with Bergeron and Marchand at the end of February. Since then, the Bruins have been clicking in just about every aspect.
That includes in goal, where Jeremy Swayman and Linus Ullmark have shared the workload and helped the Bruins overcome the failed comeback attempt by Tuukka Rask, who announced his retirement Feb. 9 after playing four games.
Swayman, a rookie, is 19-8-3, with a 2.09 goals-against average and .925 save percentage in 31 games. Ullmark, in his seventh season and first with Boston, is 20-9-2 with a 2.73 GAA and .908 save percentage in 32 games.
The Bruins are eager to display their progress against the Maple Leafs, especially given their history in the playoffs. Boston has eliminated Toronto from the postseason three times in the past nine seasons (Eastern Conference First Round in 2013, 2018 and 2019), three of the five times the Maple Leafs have qualified for the playoffs during that span.
"It's a division rival," Cassidy said. "It does matter a little more in the standings because of where we are. We haven't talked at all about the standings, other than moving up in them as the year went on. We've been able to accomplish that. Now we're back in the same area code as these other teams. We'll see how that plays out down the stretch."
Beyond that, the Bruins are a team that has found its rhythm and itself since the midpoint of the season, a team that might just strike a bit of fear in its opponents.
Though the Bruins, with all their postseason experience, aren't taking anything for granted.
"It's going to be a crazy playoffs this year," Marchand said. "I'm really excited for the playoffs this year. It's going to be a lot of fun. And whoever wins this year, I think it's going to mean a lot more than other years because the playoffs this year are so deep.
"You're going to have to win four basically Stanley Cup Finals series to win this year."