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What Burning Question Surrounds Rockies Entering Winter Meetings?

Originally posted on Colorado Rockies on SI
By Scott Roche | Last updated Dec 4, 2025 9:00 PM ET

Going into the Winter Meetings beginning on Sunday in Orlando, there are questions surrounding the Colorado Rockies. It'll be Paul DePodesta's first Winter Meetings as president of baseball operations and the first for newly-added general manager Josh Byrnes.

They have a major rebuilding job in front of them, taking over a team that is coming off a 119-loss season. There should be no stone left unturned when it comes to decisions for the Rockies. As they look ahead to building a roster for manager Warren Schaeffer next season, it'll be interesting to see which avenue they choose in terms of free agent targets and potential trades.

Getting free agents to buy in and come to play 81 games at Coors Field is not going to be an easy sell. MLB.com has one burning question for each team going into the Winter Meetings, and Colorado's is about setting itself up for success under the new leadership.

Rockies Burning Question Surrounds Their Path to Success

Jeff Lange / USA TODAY NETWORK

The Rockies have been an organization that builds from within with young players, but that has made their windows short in terms of when they are ready to contend and win. It has been a while, and they are stuck in another stretch of not contending right now. It'll be up to DePodesta and Byrnes to build them out of it.

"The new regime will be charged with doing a better job teaching and evaluating, being more active and more successful in acquiring talent from other teams, and finding wins in the margins by applying advanced information more effectively,'' MLB.com wrote.

How can they be more successful in acquiring talent? That's the question they will have to answer. Spending money and spending it wisely is one route they could go, and they could do that by adding to their pitching staff and having a tough 2025 season.

There are veteran free agent options that could look to add in Jose Quintana, Miles Mikolas, Martín Pérez, and Wade Miley. Those would be some good potential options to fill in the starting rotation behind Kyle Freeland.

As far as position players go, the Rockies had some young players step up and prove that they belong, and in terms of roster building, that's what they need. As far as building around that, adding a veteran or two through free agency or a trade is worth looking into. Whether it's a pitcher or a positional player, the front office should be smart in terms of length and money. They always have the option to flip anyone signed at the trade deadline to a contender for assets.

This is going to be an interesting first Winter Meetings for the new Rockies front office in terms of the direction they look to go in building a roster for 2026. It could shed light on what moves might be in store for next season.