Instead, he sent the 21-year-old forward packing and shipped him to the Dallas Stars, along with forward Rich Peverley and defenseman Ryan Button, in exchange for forward Loui Eriksson and prospects Joe Morrow, Reilly Smith and Matt Fraser.
The blockbuster deal ends Seguin's subpar three-year career in Boston. He never really lived up to expectations while in a Bruins sweater, and now, his $5.75 million cap hit per season is off the books.
He helped the Bruins win the Stanley Cup in 2011 with a big series against the Tampa Bay Lightning in the Eastern Conference finals. This spring, though, he struggled and had only one goal and seven assists in 22 games as the Bruins lost to the Chicago Blackhawks in the finals.
Seguin had a hard time using his speed to his advantage, and opponents controlled him by keeping him to the perimeter, which made his shot useless.
The Bruins are moving him while he's young and relatively healthy, and Chiarelli was able to get a good deal in return.
Chiarelli criticized Seguin last weekend at the NHL draft, saying the forward needed to become a better pro. Bruins assistant captain Patrice Bergeron had his former linemate's back, but understood what the GM meant.
"I think Tyler's a young guy still and he's got a lot to learn," Bergeron said. "At the same time, he's improved a lot. At that stage, when you're learning like that, that's going to happen, you need to make sure you learn from it and find a way to get better. That's the main thing with him, it's about him finding ways to battle through it, find ways and build some character out of it. He's a terrific player, a terrific person, but sometimes you need to have some lows to get back up and feel better and play better.
"I thought he was really good the way he helped us. He found a way even though he wasn't scoring as much as he would like to. He was still battling hard and doing things, the little details that you don't always see on the score sheet, but it wasn't going unnoticed from us as players and teammates. He's a terrific young player, so he's going to learn."
As for the other players in the deal:
Eriksson, 27, is a solid left winger and posted 12 goals and 17 assists for 29 points in 48 games for the Stars this season.
Smith, 22, can play either wing and posted three goals and six assists for nine points in 37 games.
Morrow, 20, is a solid, puck-moving defenseman and spent this past season at the AHL level.
Fraser, 20, is a left winger and spent the majority of the season in the AHL, but did play in 12 games for Dallas.