DETROIT - NOVEMBER 22: General Manager, Ken Holland, of the Detroit Red Wings listens to a question during a press conference on November 22, 2005 at Joe Louis Arena in Detroit, Michigan. The team was holding a press conference on the condition of player, Jiri Fischer, who collapsed when his heart stopped during a game on November 21. Fisher is listed in improved condition. (Photo by Tom Pidgeon/Getty Images)

By: Will Burchfield

@burchie_kid

Years of success and win-now thinking have finally caught up to the Red Wings. GM Ken Holland will be the first to admit it.

“It’s a draft-pick league and every year it seems for the last seven, eight, nine years, we’re missing a pick here, a pick there because we’re trying to add (players via trade), we’re trying to win,” Holland told the Jamie and Stoney Show on 97.1 The Ticket. “I think that’s what the Red Wings, with myself as GM, have tried to stand for. We’re trying to win — but at some point in time, you pay the price.”

In the 17 NHL drafts since the turn of the century, the Wings have lacked either a first- or second-round pick on 12 occasions, including seven times in the past decade. Meanwhile, due to their consistently high finishes in the standings, they haven’t picked in the top 10 since 1991 or the top five since 1990.

This organization has been skating on thin ice for a while, and this season it finally crashed through. Holland saw a chance to restock the cupboards.

“The decision that I made over the last week was, we had a disappointing year, it was an opportunity to add a lot of picks,” he said.

So he shipped out three veterans on expiring contracts, including the team’s leading goal-scorer in Thomas Vanek and its best defenseman in Brendan Smith. He also dealt underused but talented forward Tomas Jurco. The reward was a bevy of draft picks, including three third-rounders and one second-rounder.

[RELATED: Making Sense Of The Underwhelming Vanek Trade]

“Going into this trade deadline, I wanted draft picks,” Holland said. “And now we’ve got 11 draft picks in this draft, we’ve got nine for next year, and we’ve got some young people coming through the system.”

But Holland is staunch on this: The Red Wings are not burning things down and starting from scratch. He doesn’t think they need to.

“We’re going to look at (things) this summer and figure out a way to get back in the mix. It’s a fine-line league, and right now, we’re (nine) points out of a playoff spot — it’s not like we’re 29 out,” Holland said.

The other side of that coin is the Wings are 24 points behind the third-place team in the East (the Penguins) and 31 points behind the first-place team (the Capitals). The difference between contending for a playoff spot and contending for a championship is huge, and recent history suggests the only way to bridge that gap is through a full-scale rebuild.

But Holland doesn’t appear willing to make that leap.

“I’m trying to put a team on the ice that’s competitive every year, that gives our fans a reason to believe that when they go to the rink we’re competing for a playoff spot,” he said. “Do you want to go into a seven-, eight-, nine-year rebuild? These rebuilds don’t take two or three years. Once you go down that path, be prepared for eight, 10, 15 years.”

There’s certainly some truth to that. The Maple Leafs and Oilers, for example, each hit the re-set button some ten years ago and neither franchise saw a payoff until this season. And in both cases, it took a generational superstar falling into their laps to bring the rebuild to fruition. Torching the soil ensures short-term famine, but it doesn’t guarantee long-term fertility.

“We’re drafting 18-year-old players, it’s not an exact science. You’re going to miss some years, you’re going to pick the wrong players some years, and even if they do hit, those 18-year-old players – other than the superstars – have got to get to be 22, 23, 24, years old (before they can make an impact),” Holland said. “So when you start the process, it’s six years. Look, we’re trying to win, that’s what I think the Detroit Red Wings stand for. We’re trying to win, we’re trying to compete.”

But at what cost?

Last summer, Ken Holland unloaded Pavel Datsyuk’s cap hit on the Coyotes, swapping first-round draft picks to facilitate the deal. With the Red Wings’ pick, the Coyotes snagged defenseman Jakob Chychrun 16th overall. Detroit, picking 20th, was forced to settle for defenseman Dennis Cholowski. Chychrun is already playing in the NHL and looks like a franchise cornerstone; Cholowski, though a nice prospect, is still toiling away in college.

“I made the decision at the time that we needed to free up cap space and we wanted to be competitive,” Holland explained.

With all that extra cap space, the Wings signed Vanek and Frans Nielsen, only one of whom remains with the team, and dolled out raises to Danny DeKeyser and Darren Helm. The latter two contracts – six years, $30 million for Dekeyser, five years, $19.25 million for Helm – characterize Holland’s most fundamental flaw as a GM: overvaluing his own players. It’s a tendency that also led to outsize contracts for the likes of Niklas Kronwall and Jonathan Ericsson, and one that’s made it difficult to usher in a new core of players.

[RELATED: Why The Red Wings Didn’t Trade Riley Sheahan]

“You should look all around the league. Does our team have a contract or two that maybe is a little out of whack? Possibly, but many teams do. It’s the cost of doing business,” Holland said. “When you make decisions in life – every decision I make, you make, we make – they’re not all 100 percent, and then you’ve got to work around those decisions.”

The Red Wings’ bleak short-term outlook had some fans hoping Holland would blow things up at the deadline. Younger players like Tomas Tatar, Gustav Nyquist and Riley Sheahan were all rumored to be on the block. But Holland would only go so far in his pursuit of future assets.

“You can’t play with picks,” he said. “At the end of the day you can have all the picks you want, but you’ve got to put a team on the ice.”

But if that team isn’t going to win games, if it isn’t going to compete for a Stanley Cup – and isn’t that what the Red Wings truly stand for? – then who cares what it looks like? If you’re going to lose today, it ought to be in the name of winning tomorrow.