The Bruins general manager and Ottawa native spoke to Alfredsson about signing in Boston before ultimately getting a deal done with Jarome Iginla.
"After my discussions with him, no, I wasn't surprised," Chiarelli said of Alfredsson leaving the Senators. "There's a lot of similarities here, too, with Jarome. These guys are elite players in the league for a long time and they want to win. They have a thirst and a hunger, both, to win."
Alfredsson, 40, explained that wanting to win a Stanley Cup was his reason for passing up an 18th season in Ottawa to sign a one-year deal in Detroit that could be worth up to US$5.5 million with performance bonuses.
Iginla, likewise, left the Calgary Flames after a career there, though he was traded to the Pittsburgh Penguins amid a rebuilding project. While Alfredsson left a playoff team in free agency, Iginla still empathized with the long-time Senators captain's dilemma.
"I don't think he took it lightly at all," Iginla said. "By going through it, I know it's not an easy thing as far as leaving a team you've been with for a long time and made a lot of friends and life-long friends. ...
"He wants to win. We want to win. As players you want to win and I don't know which team he thinks is better or anything like that, that's not for me to say. But obviously he still loves playing and has that fire. I guess he probably feels that's his best shot."
Alfredsson and agent J.P. Barry spoke with Chiarelli during the NHL's first two-day interview period about taking that shot with the Bruins. Iginla's agent, Don Meehan, called Chiarelli later, but Boston was only going to sign one of the veteran right-wingers.
"We had had discussions in that two-day window with Daniel Alfredsson and his agent, and it was only towards the end of it when Jarome's agent called us," Chiarelli said. "So at that point, I'm like, 'I've got two really good players here and there's a lot of teams vying for those players.' I wasn't expecting or trying to get both."
Alfredsson chose to join friend and fellow Swede Henrik Zetterberg with the Red Wings, saying he'll fit well within that "culture" and praising the way coach Mike Babcock's teams tend to play. The Bruins then got a deal done with Iginla, one year that could pay him up to $6 million.
"I don't know what (Alfredsson's) assessment was as to why he thought that was the better fit," Chiarelli said, "but I respect it, the same way that I respect Jarome coming back to us and wanting an opportunity."