Washington Capitals General Manager George McPhee is arguably facing his most critical week in his 16 year tenure.

His Caps sit at 15-17-1, 11th place in the Eastern Conference and 23rd overall in the NHL, with the trade deadline just one week away on April 3rd at 3pm.

It is waters they have not chartered since 2006-07 and a team that won four straight Southeast Division titles from 2008 to 2011 with 94, 108, 121, and 107 points, respectively, and had 92 points and finished eighth in the East last season, is currently moving towards a location often called “No Man’s Land.”

No Man’s Land is a spot in the NHL where you aren’t good enough to contend for the Stanley Cup, likely won’t make the playoffs, but also aren’t bad enough to land one of the top three spots in the draft. It is a position where it is very difficult to get better quickly, just ask the Calgary Flames or the Toronto Maple Leafs, who have been the President and Vice President of No Man’s Land in the NHL the last several years. Those teams, who have rabid and demanding fan bases, have recently routinely gone with the mind set that they are only a player or two away from the playoffs or contending in them. Both have been reluctant to take a critical step back in order to possibly move two or three steps forward (that might finally be changing in Calgary this spring, but is it too late?).

The Capitals were headed to No Man’s Land once before, in the days of Jaromir Jagr, but owner Ted Leonsis and McPhee went the “blow it up” route and started over. For the most part, especially from a business standpoint, they had success and it landed them Alexander Oveckhin, who is worth the price of admission on most nights, all by himself. It is important to note that hockey is first and foremost a business to many owners. So the bottom line is vital. Thus the push to just get into the playoffs can often be the difference between being in the red or black. The bottom line can drive an approach that constantly looks at the short term solution instead of the bigger picture.

This is a danger I see for the Caps right now. They are a team that has an incredible home sellout streak of 169 games and the marketable product in Ovechkin. But everyone knows in the Baltimore/DC area that winning is your most marketable item. This region demands a winner and when a club can’t consistently do that, the fan base erodes exponentially (see the Baltimore Orioles for 14 years). So owner Ted Leonsis surely is leery of what the impacts of a losing season or missing the playoffs would do to his club that generates full building after full building these days. So it can be a risk to have a losing season.

Clearly the Caps would love to make a run and reach the postseason this year but after last night’s loss to New York Islanders, they are seven points out of first place in the Southeast Division and four points behind the Rangers for eighth place overall in the Eastern Conference. With no Western Conference matchups, it is very difficult to make up ground. To reach the post season, the Capitals will likely need to go 11-4 or something along those lines. Is that really doable with this team, one that is finally healthy and still couldn’t beat John Tavares and company, at home, in a very important game?

That is a question that McPhee needs to ask himself because the way I see it right now he has three options over the next week:

1. Stand pat and do nothing

2. Become a buyer and try to make the post season

3. Sell off some assets ensuring a post season miss but put yourself in position to snag one of the elite players in what appears to be a draft with some impact players at the top.

In option one it will be difficult to make the postseason and the Caps likely end up 9th or 10th in the East. They would have low odds to win the new draft lottery to pick first overall and probably would draft around the 10th to 14th spot in New Jersey in June. In addition, unless they sign Mike Ribeiro, they likely lose him to unrestricted free agency after the season.

In the second choice, McPhee would really need to add an impact player to get this team to go 11-4 down the stretch. It would have to be a top line winger and to do that they have to give something up, likely their first round pick this year or perhaps one of their recent first round picks (Evgeny Kuznetsov, Filip Forsberg, or Tom Wilson). It is a mortgage the future type of move that might get them in the postseason but likely doesn’t put them in a real position to contend for the Stanley Cup given what the Pittsburgh Penguins roster looks like now after acquiring Brenden Morrow and Doug Murray. Making the playoffs would help the bottom line but would the price be too great? Then they’d still have the issue of trying to sign Ribeiro along with the asset they acquired at the deadline. The Caps currently have only $15M of salary cap space for 2013-14 with just 15 players under contract. Two top six forwards would eat up much of that and McPhee still has to sign defensemen Karl Alzner who is a restricted free agent, as well as some other players. Sure the competitor in me would like to give it a shot but depending on what you have to give up this season for a top six forward asset, doesn’t appear to make a lot of sense.

Therefore, option three seems to be the smart move. Signing Ribeiro is going to be awfully tough to do and with number 9 at 33 years old and wanting a five year deal, it just doesn’t seem like a wise option on his terms. Remember Michal Nylander? That signing in 2007 arguably cost McPhee the salary cap space he needed in 2009 to shore up a Washington defense that was likely the biggest thing holding them back from beating the Penguins in 2009 and going on to win the Stanley Cup. So why hamstring yourself with a big contract to an aging player and risk that scenario all over again when you are planning on contending again?

But if you can get a number one draft pick or more this year for Ribeiro, then you should deal him. Sure you will definitely miss the playoffs but you also now have two first round picks and could package them to possibly move up to number one, two, or three and get one of Seth Jones, Nathan MacKinnon, or Jonathan Drouin. Jones, according to my sources, is the best player in the draft and NHL ready now. He very likely will be a number one defensemen on a team in the NHL in a couple of years. He’s a team changer. Snag him and you suddenly have options to possibly move some of your other defensemen, like Mike Green, who you are paying $6M a season now.

In addition to Ribeiro or Green, there are other guys on this roster that teams might be interested in such as Marcus Johansson or Joel Ward or one of the three goalies (Braden Holtby, Michal Neuvirth, or Philip Grubauer) at the trade deadline.

What McPhee and his staff need to do is work to the Baltimore Ravens model of “Right Player, Right Price.” You have to know the value you place on every player on your team and in the league and make moves accordingly. Washington’s pro scouts will really need to be doing their jobs well and feeding the GM the info he requires to make some hard decisions. If you do it right you don’t overpay for your own guys and can end up with better players at or below that price (see the Ravens getting Elvis Dumervil, Chris Canty, and Marcus Spears for the same overall amount the Cleveland Browns paid for Paul Kruger).

McPhee has made some very smart decisions on players before, such as Semyon Varlamov, who he traded for a 1st and 2nd round pick. The 1st rounder is now Forsberg while the Capitals haven’t taken any hit at all in the goaltending department. Sergei Fedorov for Theo Ruth was another blue ribbon deal by the GM that made the Caps a legit Stanley Cup contender for two straight springs. But he’s also had some not so good decisions (re-signing an aging Tom Poti for two years, the four year deal for Jeff Schultz, and the two years given to an aging Roman Hamrlik). Those contracts have impacted Washington’s salary cap while not yielding quality results on the ice.

With Ovechkin, Nicklas Backstrom, Brooks Laich, and John Carlson having long term deals clearly they are the guys for McPhee to build around going forward. Everyone else should be up grabs. It is Asset Management 101 at this point for Washington. They need to do what they can to transform a team that was one of the best in the league from 2008 to 2010, but has steadily declined, back into a Cup contender.

Sure its a risk from a marketing standpoint, but the fans in this area recognize when you are going in the right direction and will have the patience to endure a reshaping of the roster, especially if they believe it will eventually lead to Washington’s first Stanley Cup. So it’s a low risk play and if the moves are done right and there is a championship in the next few years or so, then you have people locked into your team long term (see the Philadelphia Flyers, who still sell out despite not winning a Cup since 1975).

So this is a huge week for McPhee and one he has three roads he can possibly take. They aren’t easy decisions and only he and his staff really know what options are going to be available to him in return for his current assets.

The path he ultimately chooses will likely make or break his and the Capitals future.