As the 2014 Kansas City Royals continue to do their spot-on impersonation of the 2007 Colorado Rockies, it’s been fun to remember what winning was like. Not that Colorado fans know much about that these days. In fact, when you ponder the Rockies’ recent—and unexpected—front office shakeup, the team’s inertia has been so long term and entrenched it’s easy to imagine that at some point Dan O’Dowd and Bill Geivett told owner Dick Monfort, “No, seriously, boss. We gotta go.”

When O’Dowd and Geivett resigned at season’s end, as opposed to being fired, it was a sign that at least someone among the Rockies’ brass realized that a massive overhaul is needed. What remains to be seen is if the owner realizes it, too.

After four progressively worse seasons—the number of losses has fluctuated, but the sense of hopelessness has soared—we’re about to see if the new guy, Jeff Bridich, has the vision and ability to make these desperately needed changes. But the bigger question is whether he has the permission to do what’s necessary to turn this team around.

The Rockies didn’t even bother to conduct a GM search, promoting Bridich from within the organization. His resumé seems impressive. His youth and Harvard education suggest he’s attuned to the advanced metrics that have become an increasingly important part of strategy and player evaluation. Because Colorado’s altitude will forever force the Rockies into a unique situation, maybe there’s some elevation-conscious statistical alchemy that can be applied to assembling the roster.

That’s where the dilemma starts: Between Troy Tulowitzki, Carlos González, Nolan Arenado, Wilin Rosario, Michael Cuddyer, Justin Morneau, Charlie Blackmon, Corey Dickerson, Jorge De La Rosa, and a few others, the team’s roster has individual talent that could play for anyone. The problem is, that talent hasn’t congealed into a cohesive team.

Job number one for Bridich this winter will be to figure out which of these players to keep and build around, and which to shop. He’ll be hamstrung for now by the un-tradability of Tulo and CarGo, theoretically his two biggest assets. Unloading those two massive contracts for prospects would be a legitimate sign that the Rockies have a plan. Unfortunately, their lengthy and current injury problems mean that no right-minded team would make an offer until they’ve seen that the two players are healthy again.

The Rockies’ other pressing concern, as always, is pitching. MLB is currently going through a power arm phase, in which most teams have several guys who routinely throw high-90s heat. But while these pitchers roll up the Ks, they also tend to give up a lot of fly balls, which is poison in Colorado. Finding pitchers in the mold of De La Rosa, more crafty than flamethrowing, would help at home and on the road as long as the team’s defense is sound. (It’s been so-so of late.)

Finding takers for players such as Morneau, Cuddyer, and Blackmon also wouldn’t be a bad idea. Any of them might appeal to a good club looking for a veteran or two, and their maturity and leadership, frankly, is being wasted on a team that can’t hope to contend for at least a few more years.

For an example of how an overhaul should unfold, Bridich might want to look toward Chicago, where the Cubs’ Theo Epstein has spent several seasons dismantling an overpaid and unproductive roster. He’s lost a ton of games in the process, but the Cubs now have an incredibly loaded farm system that will begin to pay serious dividends over the next few seasons.

Professional teams must constantly reevaluate whether they’re in “win-now” or rebuilding mode. For the past several years, the Rockies have been trying to do both, which is a great recipe for mediocrity. But after 96 losses (and 88, and 98, and 89), it’s abundantly clear that the one and only way to go now is a full-on makeover. How this offseason plays out will tell us whether the guy signing the checks finally gets what’s long been obvious to Rockies fans.

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Follow 5280 editor-at-large Luc Hatlestad on Twitter at @LucHatlestad.