How a Division-Rival Lefty Could Save the Padres’ Offseason

Padres general manager A.J. Preller needs to find a way to salvage the offseason.

San Diego currently has little financial flexibility and a depleted farm system, leaving few obvious paths to improve the roster. After losing multiple star players without adding any notable replacements, the Padres’ playoff outlook has dimmed considerably. Even more concerning, the organization lacks both the payroll space to upgrade the roster and MLB-ready prospects to fill any holes.

There is, however, one surprising move that could reset the entire offseason: a trade for Rockies starter Kyle Freeland.

Yes, that Kyle Freeland - the division rival left-hander who finished the 2025 season with a 4.98 ERA and a 4.18 FIP.

Freeland is owed $16 million in 2026 and has a $17 million player option for 2027 that triggers if he reaches 170 innings pitched. It’s a terrible contract for Colorado, but one that could make sense for San Diego if paired with a salary swap involving shortstop Xander Bogaerts and the right assets.

The Rockies are in the midst of a rebuild, and at 32 years old, Freeland no longer fits their timeline. His performance since 2022 - 4.91 ERA and 4.61 FIP - combined with his salary makes it unlikely Colorado could receive meaningful prospect value in a trade.

Unless, of course, the Rockies were willing to take on an even worse contract.

That’s where Bogaerts comes in.

Padres Receive

Kyle Freeland

Rockies Receive

Xander Bogaerts
Humberto Cruz (#3)
Jack Costello (NR)

Ranking just 23rd in payroll tax, Colorado has the financial capacity to absorb long-term money in exchange for prospects. Bogaerts, while expensive, arguably makes more sense for a rebuilding Rockies club than Freeland. Pitchers rarely thrive at Coors Field due to altitude challenges, making the development of a frontline starter unrealistic. Offense, however, is a different story.

In a hitter-friendly environment, Bogaerts could regain some of his production at the plate. If he does, the Rockies could eventually flip him after eating a portion of his contract, turning Freeland into real future assets - something that would otherwise be impossible.

For Preller, the appeal is obvious. Bogaerts is owed $25 million in 2026 with eight years remaining on his deal. Moving that contract would free roughly $10 million in payroll immediately. Flexibility the Padres desperately need to improve the roster.

Freeland also fills an on-field need. Entering spring training, San Diego’s projected rotation features four right-handers and just one lefty, JP Sears, at the back end. Freeland would add left-handed balance while providing competition for Sears, who posted a 5.04 ERA and 5.21 FIP in 2025.

With Freeland in the mix, the Padres would have two solid-upside southpaws at the back of the rotation. Betting that at least one performs well in 2026 is a reasonable gamble.

Teams are typically reluctant to trade within the division, but this is one of the rare cases where the risk may be worth it. The Rockies gain future assets for their rebuild, while the Padres finally get some financial breathing room - something Preller has been searching for all winter.