The Detroit Red Wings set a standard of excellence that won’t be repeated in the modern 31-team salary cap era: 25 straight trips to the playoffs, six Stanley Cup Finals appearances, four Stanley Cups.

That era is over.

I spent my 17-year career in different NHL front offices during this historic Red Wings run. We would emulate Detroit. We would hate them. But we didn’t often beat them. I had a front-row seat to their dominance, losing to the Red Wings in both the conference finals with the Dallas Stars and the Stanley Cup Final with the Washington Capitals. It wasn’t pleasant.

I have also been part of a couple of different rebuilding efforts during this time, which gives me some perspective on what the future looks like for Red Wings GM Ken Holland and his staff as they begin the process of climbing back toward the impossibly-high bar they have set for themselves.

Rebuilding (or retooling, or whatever other “r” word you want to use) is never an easy task for an organization that has experienced sustained success. It’s really difficult to objectively analyze where the sun will shine tomorrow when you are looking through the shadows of the past. I saw that firsthand when I arrived in Dallas in 2006, as the Stars struggled to put their 1999 Stanley Cup win of 1999 in the rearview mirror and it ended up delaying necessary (and difficult) roster separations that arguably had a hand in owner Tom Hicks losing the franchise to bankruptcy. When that sustained success is historically long, it makes the process that much harder.

The competitive NHL landscape is dynamic, and has been changing at a rapid pace. There is no guaranteed road map to playing into June.

Maneuvering your roster for the top draft spot (affectionately known as ‘tanking’) can sound enticing when you look at Connor McDavid, but that walk through the Valley of Death for a franchise can be long, daunting and, ultimately, uncertain. Rebuilding on the fly usually sounds better to a team’s business operations group, but it runs the risk of failing to move the needle past the point of mediocrity.

I have been in both camps. In 2004, we stripped the Capitals down to the floorboards to get Alex Ovechkin. During my time in Dallas, we tried to be competitive, make the playoffs and still build for the future. With both experiences in mind, here is my risk/reward analysis on the key aspects of the Red Wings roster renovation that GM Ken Holland is facing.

Hoarding draft picks: It’s hard to argue with a rebuild strategy that involves acquiring multiple draft picks. It was a core element of both of my experiences in Washington and Dallas. Having said that, I believe the ground has shifted substantially in the last few seasons. If you really want to move your franchise out of mediocrity with a buckshot draft strategy, the key is devoting care to where the picks are as opposed to how many picks you have. In a comprehensive NHL draft study that I referenced as a value benchmark (using 160 NHL games played as a metric of “selection success”), a player picked in round one had a 64 percent success rate. Rounds two and three yielded a roughly one-in-four shot at an NHL player (28 percent and 24 percent, respectively). Rounds four through six had virtually identical success rates, around 13 percent, and round seven picks were unsuccessful about 93 percent of the time.

The first round is obviously the most valuable from a prospect standpoint, but what’s really interesting from a tank vs. on-the-fly scenario is the intra-round success variation. The top third of the first round yielded NHL players around 85 percent of the time. Outside of the first ten selections, the yield fell to about 50 percent.

Simply put, pick quality matters, and perhaps never moreso than now, when 18 and 19-year-old, high-end players are coming into the NHL and making an impact.

That’s not to say you can’t find a gem in the later rounds like Henrik Zetterberg (No 210 overall in 1999) and Pavel Datsyuk (No. 171 overall in 1998), but this strategy is relying much more on luck than odds.

Signing veterans on short-term deals to use as trade deadline assets: This is a solid strategy for the Red Wings if they can execute it, but there are three significant obstacles that you simply can’t control with this plan of attack. First, there is no guarantee that these second-tier free agents will perform at a level that makes your team competitive. Next, the return for these players at the trade deadline fluctuates, and I personally believe that the trend is moving away from teams paying draft-pick premiums in March. Thomas Vanek is a good example, fetching only a third-round pick from the Florida Panthers despite being productive for the Red Wings. Instead, the pendulum seems to be shifting towards the blockbuster summer trade.

Lastly, if you sign veteran players that actually do make you competitive and put your team in the playoff hunt, it becomes difficult to trade them for mid-round picks that are likely giving you about a 1-in-8 shot at getting an average NHL player three to five years down the road.

I experienced this exact scenario with the Dallas Stars. We signed defenseman Sheldon Souray as an off- season reclamation project in our rebuild-on- the-fly/bankruptcy days of 2011. He played well and we had interest from other teams in Souray at the deadline, but the best offer in return was a fourth-round pick. We were also in a dogfight for the No. 8 and final playoff spot. In the end, we opted to keep the player and try to make the playoffs, which we deemed (right or wrong) to be more valuable at the time than the future return.

Use free agency to eventually land a franchise player: In my opinion, this is a sucker’s bet that many rebuilding teams fall into, particularly teams with a history of being the alpha males of the NHL, like the Red Wings have been. Virtually every team in the NHL thinks they are special in some way, shape or form (ok, maybe not Winnipeg). This is even more pronounced when you have actually been special. Organizational hubris gets woven into your DNA, and only gets worse when you start filling the front office and coaching ranks with former players from your golden era.

Everyone drinks the Kool-Aid, and there is often no voice in the room to offer a counter-balancing opinion. The real danger here is that you lose perspective of where you actually are in your competitive cycle and then compound this by making poor free agent and/or contract decisions to reinforce your perception of being a destination franchise.

A case in point: The Edmonton Oilers, before current GM Peter Chiarelli arrived. Despite their future being bright with Connor McDavid and his young supporting core, one of the reasons it took Edmonton a decade to escape the bottom of the NHL standings was because it was locked in its own echo-chamber of the glory years of the Wayne Gretzky era. Everyone in the hockey world outside of northern Alberta could see this except the people running the team.

The solution

Based on my experience, I would base my strategy on three main premises:

What are the expectations of ownership and where is the franchise in its business cycle?

How robust and hockey-sophisticated is the fan base?

What is the state of the team’s core on both a skill and age basis?

From my standpoint, the lower-risk rebuild-on-the-fly strategy makes sense for a franchise in a non-traditional hockey market where a full-on tank will devastate the organization’s revenues and where simply making the playoffs will resonate with the fan base. That is not Hockeytown as we have come to know it.

If I were running the Red Wings (which admittedly I am not), I would opt for the higher risk-higher return strategy of stripping the team down and doing a total rebuild through the draft lottery. This is never a fun discussion in the executive suite (particularly with a new building opening for the 2017-18 season) but I would argue that the timing of the opening of the Little Caesars Arena will serve to soften the economic blow of stripping the roster down competitively.

The Red Wings simply don’t have the young horses you need to build around in order to compete at the elite level in the modern NHL, and I think they need to have a table at the front of the draft floor for a few years in order to acquire them. Moreover, they have a fan base with a high hockey IQ that will both understand and support the rationale behind a full-blown rebuild. Playing an extra few home games in April will simply not cut it in a sophisticated hockey market that both understands what it takes and expects to win championships.

The Detroit Red Wings did not manufacture one of the longest periods of competitive excellence by being risk-averse. Now is not the time to start.