Tyler Seguin Signing Was the Beginning of the End for Peter Chiarelli in Boston

Sometimes it's difficult to pinpoint when it all started to go wrong for someone. There are a host of internal, external, known and unknown factors that can make it difficult to discern when things began to fall apart.

It's easy to spot that moment with Peter Chiarelli; it was when he chose to give Tyler Seguin a six-year, $34.5 million contract on the eve of the 2013 NHL lockout, a move designed to get long-term value out of a budding star.

It's not that the contract wasn't and isn't a bargain for the team holding it, because it truly is for the Dallas Stars. It's that Chiarelli misread the player, both his future production and actions once he had a long-term deal, and the butterfly effect it would have on the Bruins' salary-cap structure in coming years.

It's ground zero for why Chiarelli was fired Wednesday morning, right around the same time a jury found New England Patriots tight end Aaron Hernandez guilty of first-degree murder.

Credit the Bruins, for the announcement represents perhaps the greatest news dump in sports history.

If only Chiarelli was as good when it came to dumping players in an attempt to keep the win-now Bruins winning now.

The problem of keeping a competitive team competitive in a salary-cap league is one that GMs attack in their own way. When the Chicago Blackhawks won the Stanley Cup in 2010, they faced all sorts of salary-related issues, which is why Dustin Byfuglien and Andrew Ladd found themselves in Atlanta after the season. When painting oneself into a corner, it's important to leave a window open behind you.

Chiarelli took out that paint brush when he gave Seguin that contract, as it turned out the salary cap would not rise as much as he or many others projected, putting him in a difficult position with Tuukka Rask and David Krejci also needing new contracts. Faced with a difficult decision, Chiarelli traded Seguin along with Rich Peverley to the Stars for Loui Eriksson, Reilly Smith, Joe Morrow and Matt Fraser.

Michael Dwyer/Associated Press

It was a gamble from the moment the Bruins phoned NHL's Central Registry, and it's one the Bruins lost. It was based on real-world, tangible issues, like the salary cap, but also ones that are only problems if you choose to let them be, like the idea that Seguin partied too much, was immature and didn't play the game the Bruins way, which based on 2014-15, is at a snail's pace as quicker teams fly past you and win games.

Seguin led the Bruins in scoring in 2011-12 and showed all the promise one would need as a 20-year-old former No. 2 pick. But the Bruins' brain trust, with Chiarelli as the cerebellum, decided Seguin's immaturity didn't fit the Bruins' blueprint and that by acquiring Eriksson and Smith, especially, the Bruins could continue to compete for Cups.

The Bruins may have also overreacted to Seguin's one goal in 22 postseason games in 2013, as he played much better than those numbers indicated (his 70 shots were fourth-most in the playoffs) and putting too much stock in any season that begins in January can be foolish.

But it's unfair to say Chiarelli was fired solely because of Seguin budding into a cornerstone player in Dallas. Yes, the Bruins should've anchored themselves to Patrice Bergeron and Seguin as their top two centers, but there was so much more than that.

There's Milan Lucic making $6 million per season and Chris Kelly at $3 million. While Seguin is 23 years old and in the middle of a deal with a $5.75 million cap hit, 29-year-old David Krejci embarks on a six-year, $43.5 million contract next season. 

Giving Jarome Iginla a bonus-laden contract isn't an issue, but the cap complications it caused this year that led to Johnny Boychuk being dealt for a draft pick is a major issue. Breaking up a team as collateral damage from a championship is one thing; doing it for seven playoff wins won't cut it for ownership.

All the moves Chiarelli made in the wake of signing Seguin were with an eye on the present, and it's led to a sharp drop-off from Cup finalists to second-round losers to missing the playoffs altogether. With 38-year-old Zdeno Chara in obvious decline and three more years on his contract with no heir apparent (like Boychuck) to fill the void, the Bruins don't figure to be contending for championships again any time soon.

Chiarelli had difficult decisions, no doubt, but many of them were made more difficult by the ones he made in the past. If he waits until after the 2013 lockout to give Seguin a shorter, cheaper, prove-it deal instead of dumping $34 million on his front lawn, maybe Seguin feels less untouchable, or maybe the Bruins feel more comfortable with Seguin's off-ice issues and let him grow through them.

It worked for Chicago and Patrick Kane, after all.

There was plenty of good to go with the bad for Chiarelli, who won a Stanley Cup in 2011 and fell agonizingly short in 2013. But the bad outweighed the good, especially the past three years.

All statistics via NHL.com. Advanced stats via Stats.HockeyAnalysis.com and Puck On Net.

Dave Lozo covers the NHL for Bleacher Report. You can follow him on Twitter: @DaveLozo.