We are nearing the stretch drive for the NHL season. A few teams are out of it and looking toward the draft. A few teams have established themselves as regular season leaders and are trying to maintain the high level for the games that really matter. And a bunch of teams are in dog fights for positioning or to make the 8-team cutoff.

It is that time when everyone has had a long look at their personnel, style of play and most importantly on ice success and has to ask the questions about what it takes to take another step up be it via trade or just getting more out of what they have.

Here are 15 questions (1 for each team) in the Eastern Conference:

1) Boston. It has become clearer and clearer that the Bruins are the best team in the East right now. They are strong in all areas and are deep in goaltending (pending possible Fernandez trade), defense and young legs with some skill on offense. But the playoffs have been very unkind to Eastern Conference frontrunners in recent years. In 05-06, Ottawa was by far the class of the league into early winter only to make an early playoff exit. In 06-07, it was Buffalo that dominated the 1st 2/3 of the regular season, and while they did go deep in the playoffs (conference finals), arguably the best team in East that season did not get a spot to play for the Cup. And though Pittsburgh was near the top in 07-08, people might forget that it was the Canadiens who entered the playoffs #1 with a lot of high hopes.

So what does it take for the Bruins to carry their "best in the East" title all the way through the playoffs? Maybe another veteran or 2 for depth and moxy at the trade deadline? Or...?

2) Washington. It pains me to say it, but I think the skaters on this team are ready. I think Ovechkin has distanced himself as the best player in the league. Other young stars like Green and Semin have arrived. And the team has gradually and quietly assembled a better blue line and deeper forwar corps.

But is Theodore really capable of playing on a Stanley Cup winner in net? Yes, I realize that he has been better of late. I also realize that he was decent down the stretch with the Avs last season and won a round in the playoffs. And yes, I remember that he was the best in the league at 1 point. But when was he really last a player you would want to pin a good team's hopes on to be solid. Maybe 2004? I do not think it is impossible that Theodore find it at the right time on the big stage, but I am skeptical. If I were GM in Washington, I would be exploring my options for goaltending depth at the trade deadline. Might Toronto part with Toskala for young quality? Can they wedge a bigger contract into their salary? Or is Theodore really the guy?

3) New Jersey. What happens when Brodeur returns? If you take what New Jersey has done this season and then make the easy paper switch of Brodeur for Clemmensen, this team looks incredibly impressive. But is it possible that the "we all need to pull together" rallying cry helped them overachieve a bit such that their is a bit of a sigh of relief and not that much improvement when Brodeur returns? No way do they get worse with the hall-of-famer returns, but it will be interesting to see if they can get a ton better in which case they become a Stanley Cup frontrunner.

4) Flyers. Is this the team lying in the weeds in the East? Though he has played some, Briere could almost be considered a trade deadline addition for this team that has mostly gotten by without him. For a team heavy on big, nasty and physical on the forward lines, he provides nice complementary speed and skill. And Carter and Richards have turned into just what people were hoping for a couple years back. Suddenly this team is incredibly deep at forward with decent 2-way players and a nice miss of size and skill. And while I think they are at least 1 player short on the blue line, there are some good pieces in emerging Coburn, decent puck mover with some defensive conscience in Timonen, etc. If you start looking at forwards past #4 or #5 on the depth chart, they are arguably as good/deep as anyone in the league which does a lot for scoring come April when things tighten up and you need to find goals from more places.

5) Montreal. Is this Price's year? And can this team fight through injuries and a bit of a lull to refind the level they were playing at in the fall? Price's track looks a little bit like Fleury's. Like Fleury, both were highly touted with 'can't miss' expectations heaped upon them at an early age. Both also found themselves in the playoffs early with a pretty good hockey team with a chance to go deep in the playoffs (so no easing into the playoff thing as an underdog and a year to get their feet wet without the pressure). And like Fleury, Price looked a bit shakey in his first playoffs. Fleury came back the next season to play very well and help his team reach the Stanley Cup finals. Can Price follow this same path?

And is the team even good enough right now? In October and November, the answer appeared to be yes. But this team has been good not great at best more recently. There are injury issues which could clean up at just the right time, but is that the only problem? Might this team need a couple more players to truly challenge for the Cup (assuming Price is ready)?

6) New York Rangers. What are they going to do for scoring at wing? I like Gomez and Drury down the middle come playoff time as much as any center combo in league (except maybe the high octane Pens). Both are veterans with fire, playoff experience and are the kind that just win battles when it matters. But Gomez is very much a playmaker first and a scorer 2nd. And Drury is really the absolute version of a checking line center who can score like a 2nd line center. He is a 25ish goal scorer who saw a couple bigger seasons playing on a Buffalo team where everyone that scored in bunches. The point is not at all that there is anything wrong with either player. I would take the Rangers centermen for the playoffs in a heartbeat. But the team needs scoring from the wings. Early in the season, offseason acquisitions like Naslund and Zherdev combined with a couple holdovers seemed to fit perfectly. But of Naslund's 15 goals only 2 have come in 2009. Similarly Zherdev scored his 1st 2 goals in 2009 on February 6. Callahan has registered only 1 of his 12 goals in 2009. You have to think that this team will do something to provide scoring on the wing come April and later. Otherwise, I think they get stuck trying to win too many games against good teams 2-1. Who do they get at wing? And can they find chemistry quickly enough?

7) Can Miller carry this team to the playoffs? Especially minus Vanek for 3-4 weeks, Buffalo looks like a team destined to finish between #7 and #10. I do not think they are good enough to surge any higher, but I think they are deep enough in terms of good but not star talent that they are clearly in the playoff chase until late. But in between some good wins lately, they have also had a good number where they asked a ton, too much, from Miller and got it. Asking your goalie to win games too often is usually not a recipe for long-term success, but just Maybe Miller is up to it. With any falloff in Miller's play, I think this team suddenly looks very different. But I would not bet on it happening.

8) Carolina. Can their young leaders lead? Especially with BrindAmour suffering through a tough season limited by a hasty return from 2 knee surgeries, Staal needs to lead this team. He has not been bad at all so far. The 2-way part of his game has improved immensely since his breakout year in 05-06 to the point where he is a regular on the penalty kill and takes big defensive zone draws late in the game. But the team really needs him to be a factor each and every night down the stretch for it to make the playoffs. And Ward needs to similarly be the guy night-in and night-out in net. This team is good enough to claw itself into the playoffs, but also average enough that they will not be able to make up for it if they have 6-7 nights down the stretch where their goalie does not give them a chance.

9) Florida. Can their all hands on deck approach be the answer? As a Canes fan, I have seen the same story in the Southeast Division for years with Florida. They are weak early and then somehow surge late still to fall short. And in the past, the Panthers have been led by a name guy carrying the mail late. First, it was Luongo stealing games they did not deserve down the stretch. More recently it was Jokinen surging late for wins. But the 08-09 Panthers are much more the everyone kicks in approach. Vokoun can be very good when he gets going, but he is not Luongo especially in 08-09 so far. And it is likely that this team will not have a single 60-point scorer. When things get tense late in the season and goals become harder to come by, can this team get enough offense without true go-to guys to score goals? On the one hand, it is not clear how you try to shut them down because the offense comes from a variety of sources. On the other hand, March is often carried by superstars rising up at the right time.

10) Pittsburgh. Somewhat like the Rangers, who provides the secondary scoring and goals from the wing? Sykora has been decent and steady, but the Satan experiment has not gone that well. The Pens are the only team I would put ahead of the Rangers in terms of strength down the middle especially with Staal sitting all the way at #3. And who can fault a powerplay of Crosby, Malkin Gonchar and whoever? But minus Malone and a couple other players as they maneuver their salary to keep the big guns, this team is looking a little bit like the Lightning team post Stanley Cup. They are impressive at the top, but not incredibly deep in terms of quality. Can they find a wing or 2 and maybe another stay-home defenseman to get deeper? Top end talent does often carry the day in March, so is it possible that Crosby and Malkin find the next gear and none of it matters?

11) Toronto. Which direction do they go in terms of building for next year? I refuse to believe that this franchise is willing to wait even a few years to try to get a lot better. For whatever reason, they have not had much luck in the free agent market the past couple years be it because they were holding to the "build through youth" or be it for whatever reason. There are some big names being bantered around already as trade bait. Will Toronto be a seller and get more youth and look to next summer for big $ additions? Or will they not risk being left out of the free agent race and look to add players who are already under contract?

12) Tampa. Is it finally time to break it up and start over? The Lightning picked the worst time in terms of salary structure to win the Cup. After winning it all in 03-04, they had too many big names to sign for huge $ and never recovered. Khabibulin and other important secondary players had to leave, and the team still has not successfully filled in behind them. Richards left last season. Is it time for Lecavalier and/or St. Louis to finally end the yearly string of rumors and leave setting this team up for a true rebuilding?

13) Ottawa. When does management look in the mirror? Since playing in the finals only 2 years ago, this team has been whirlwind. Coaches come and coaches go, but the results mostly go. The GM botched the goaltending after the unfortunate Emery situation. The team continues to have trouble building anything past the pizza line (or whatever it is being called these days). This team is not as far away from being good as their 08-09 record looks, but someone needs to right the personnel ship.

14) Atlanta. Are the Thrashers, the NHL franchise in the most trouble right now? First, I have done nothing to dig into detailed financials, so I do not claim to have any great scoop on details. But a couple facts jump out: 1) This team is not very good right now; 2) While there are some decent young players, I would not put them even close to being an LA or StL who seems to have bunches of high-end young quality; 3) Even if they do rebuild successfully, can this fan base wait? They waited and waited and then got only a tiny, bitter taste of the playoffs after leveraging a bunch of future (most notably Coburn) to get Tkachuk and Zhitnik for an ugly 1st round playoff loss. I have no idea which way you go with Kovalchuk. On the one hand, he is truly a reason to buy a hockey ticket today. On the other hand, he is not enough right now and could bring a lot in trade. Regardless, minus a huge offseason or incredibly fast development, this team suddenly looks 2-3 years out from the playoffs which could be too far.

15) New York Islanders. If you are in rebuilding mode anyway, the approach of signing some decent veterans to short contracts can be a good one. You get these guys in the locker to set the tone and teach the kids. And then you have quality rental trade bait come February if you do not surprisingly find yourself in the playoff hunt. How much can the Islanders get for guys like Weight, Guerin and maybe even someone like Witt? Parlay that with another high draft pick and just maybe this team starts looking like a rising StL team.

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