Obviously, there is no single factor that determines which side of this equation a team ends up on. There is however, one that I believe overshadows all of the others. The factor I am referring to is the culture of the organization. Most organizations talk about building a strong culture, but few take the necessary (and often difficult) steps required to build a winning culture.
It takes time and commitment, as well as a lot of pain to create a winning culture. Most people shrink in the face of the difficult decisions that must be made to build a strong lasting culture. Instead they opt to make decisions that have the most immediate impact.
Winning cultures are built through strong and consistent leadership. I have seen exceptional cultures begin to fall apart as soon as one decision strays from the written and implied rules of that culture.
People who know how to build exceptional cultures are well aware that they will often have to accept short term losses by adhering to the rules of that culture. They also know that those losses will pay off handsomely if they stay on their path. It is also imperative that they have buy-in from ALL levels of the organization.
Most preseason predictions focus on changes made to a roster or coaching staff during the off-season. While this is indeed an important consideration, I would argue that without bringing them into a living, breathing culture they are, more often than not, doomed to fail.
People often become better than they imagine they could be when they are dropped into a winning culture. There's a reason that companies like In- N- Out Burger and Southwest Airlines are among the most successful in their field and have the most satisfied employees, while many of their less successful competitors have some of the unhappiest employees.
The reason is the difference in culture. It's not like In-N-Out and Southwest hire all the best and brightest and their competitors hire bums. In fact, I would be willing to wager that if you switched the new hires from In-N-Out and Southwest with their competitors' new hires, nothing would change at any of those businesses.
In football terms, the New England Patriots are arguably the most dominant (and consistent) team in football over the past 20-years. How many times in the past decade have they acquired the best available players in the off-season?
Look at their most valuable player, Tom Brady, he was not a highly sought-after player when he arrived there. It's very likely that if he went to the Cleveland Browns instead of the Patriots, no one reading this (outside of University of Michigan fans) would know who he is today.
That's the power of a winning culture. I always say 'you become the average of the five people you spend the most time with, so choose carefully.' In a nutshell that's how a winning culture works, you become the average of the people who are already in that culture. Which is why bringing a bunch of great new players to a team often disappoints that team's fans.