With Peter Chiarelli's contract extension set to be formally introduced Tuesday at the Garden, we give you five thoughts about the move and the Bruins general manager:

1. The hardest part of Chiarelli’s job is what’s coming up, not what he’s done so far. Let’s be real: the progress the Bruins have shown has been substantial, but it wasn’t all Chiarelli’s doing (more on that below) and it’s not like his team is truly a Cup contender yet. Sorry, Bruins fans. They would have been thumped by Pittsburgh. So let’s hold off on the parade. Chiarelli took a broken down program and returned it to respectability. We all believe the Bruins are headed in the right direction. But that’s all. The farthest they've gotten during his tenure is the second round. Let's not get ahead of ourselves.

Now come the real decisions. Who do they pay, and how much do they pay them? Who is expendable and who is essential? Chiarelli hit a home run with David Krejci. The 23-year-old centerman is already one of the best players on the team, and he’s locked in for the next three seasons at under $4 million per year. That’s outstanding value. But I think Chiarelli blew it with Tim Thomas. Four years and $20 million for a 35-year-old goalie who has never been out of the second round? An annual cap hit of $5 million when you might have someone better coming up through the system in Tuukka Rask? Have you gotten that juicy rebound Thomas served up to Scott Walker out of your head yet? I haven’t.

I’m not saying the Thomas decision was an easy one. None of these choices are. But that’s why the Bruins are presumably paying Chiarelli the big bucks. Okay, these are still the Jacobs’ were talking about. This is why they’re paying him some bucks. He has to be right a lot more than he’s wrong. 

Let’s say the Bruins add no pieces from outside the roster this offseason. Ask yourself this question: Do they have enough to actually win a Stanley Cup? If all of their young players progress as they believe they will, do they have everything they need in-house? This is what Chiarelli has to decide. I hope he decides that the answer is no, because that’s what it looks like from here. The B’s don’t quite have enough. So who can Chiarelli live without and who does he need? Keep in mind: The B’s are tight up against the cap; one mistake could be fatal.

Again, those decisions are going to be substantially more difficult than the ones he’s already made. It’s a lot easier to build a contending team than it is to build a champion. Now comes the hard part.

2. No. 1 need on the roster: Defensemen who can move the puck. I hate to take you back there, but in that Caro lina series the Hurricanes were able to expose the B’s fatal flaw. Namely, when the system breaks down, the B’s don’t have enough cool hands on the backline to move the puck and transition from offense to defense. The B’s were terrific in this regard during the regular season because Claude Julien has a great system and he got his players to buy into it. But as the B's found out, even the best systems break down in the playoffs. The intensity is too high and the pressure too great. You need players who can skate and stick-handle their way out of trouble and the B’s didn’t have nearly enough of them. If there was a time-of-possession stat in hockey, the Hurricanes would have dominated it in the series. There were countless times when the Bruins just couldn’t get the (bleeping) puck out of their own end, and it cost them.

I think it’s wishful thinking to say that injured defensemen Andrew Ference and Matt Hunwick would have been the difference. Something tells me that even had they played against Carolina, the story would have been roughly the same: too many games where the action was played more in the B's end than the Canes' end.

Maybe I’m wrong about that. But, again, this is what Chiarelli has to decide. Do the likes of Dennis Wideman, Ference and Hunwick do the trick? Or does he need more talent (Florida’s Jay Bouwmeester?). Chiarelli has a surplus of bodies, and salary, at forward. Can he turn some of those assets into blue line help? Which leads us to…

3. The Phil Kessel question. Yes, he led the team in scoring. And, yes, in today’s NHL goal-scorers are valued as high as anything. And at 21-years-old he should have tremendous upside.

 That’s should. Count me among those who think we saw Kessel’s ceiling in 2008-09. That is, a 36-goal scorer who has great wheels but not enough moves and not nearly enough toughness. If you had the cap room to keep him, then fine. Keep him. But the B’s don’t have the room and he’s the piece I would start with. He sure looks sexy on paper. The goals. The age. The draft position (No. 5 overall in=2 02006). He’s great trade bait. Now, if you watch him every night -- if you actually see him get knocked off the puck around 15 times a game by the left defenseman -- then you realize that sex appeal doesn’t always translate on the ice. But maybe there are teams around the league who are willing to ignore that and give you some talent in return. If I’m Chiarelli, that’s what I’m exploring right now.

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Audio on Demand

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Tickets

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Boston Red Sox vs Northeastern - JetBlue Park, Lee County , FL
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03/3/2012

Boston Red Sox vs Boston College Eagles - JetBlue Park, Lee County , FL
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03/4/2012

Boston Red Sox vs Minnesota Twins - JetBlue Park, Lee County , FL
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4. I wonder if Chiarelli and Julien will be able to make the hard call with Thomas if it comes to it this year. How objectively will they be able to judge their all-star goalie,  the guy they just gave $20 million to and who very well could be the defending Vezina Trophy winner? Thomas has been very good for this team, especially in the regular season. The fans love him and his teammates believe in him. But what if Rask is better? What if the quiet, steady style of the 22-year-old Fin is more conducive to a deep playoff run? Will Chiarelli and Julien have the nuggets to make the switch?

Check back in April on that one.

5. Finally, Chiarelli is going to get a lot credit today for putting the Bruins back on the map. And he deserves it. He’s made a lot of good moves. But I also think it’s important to point out that Mike O’Connell (yes, that Mike O’Connell) and the assistants he left behind contributed more to this team than folks realize.

Actually, if you look at it one way, the current roster belongs more to O’Connell and assistant Jeff Gordon than it does to Chiarelli. Krejci, Patrice Bergeron, Byron Bitz, Matt Hunwick and Mark Stuart were drafted during the O’Connell regime. O’Connell was also responsible for bringing in your beloved Thomas. O’Connell was gone by the offseason of ’06, when Chiarelli was in limbo between Ottawa and Boston, but Gorton was not. He was on the masthead when the B’s drafted Lucic and Kessel and signed Marc Savard and Zdeno Chara in free agency. Gorton was also technically in charge when the B’s traded Andrew Raycroft to Toronto for Rask. Of course, many believe that Chiarelli was pulling the strings from Ottawa at that time and Gorton was merely a warm body. Whatever the case, it’s clear that O’Connell and Gorton had found their stride when it came to the draft by the time they were shown the door. A mention to director of player personnel Scott Bradley, who has been a prominent piece throughout the transition, is also in order.

It's also clear that while O’Connell may have been picking the players well, the Bruins had stopped developing them by the time Chiarelli arrived. The picks were there, but the flow through system wasn’t. Chiarelli and Julien restored it, and that is perhaps their greatest accomplishment.

Now it's time for Chiarelli to really earn his money.

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Michael Felger can be seen on “Sports Sunday” on Comcast Sportsnet, Sundays at 10 p.m. Reach him at mfelger@weei.com.