Mile High Sports

Strike 3: Would the Rockies ever trade Kyle Freeland?

Mar 27, 2026; Miami, Florida, USA; Colorado Rockies starting pitcher Kyle Freeland (21) exits the game against the Miami Marlins during the fifth inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images

The new regime of the Colorado Rockies will face a new kind of test as we ease into the early summer months. Can they – will they – break with longstanding Rockies tradition, and part with any fan favorites at the trade deadline in an effort to continue rebuilding this roster on the fly?

They’ve already proven they want to do things differently than the folks they replaced. They’re going to build the Rockies roster in a far different manner that their predecessors, using more analytics and less emotion. That could include saying goodbye to formerly prized prospects and current players who have been productive and loyal to the organization for more than a few years – but who hstill ave trade value.

The Major League Baseball trading deadline is Monday, August 3rd. By the time the first pitch is thrown in that evening’s Rockies vs. Rays game at Coors Field, Rockies stalwarts like Antonio Senzatela – who is having a remarkable and totally unpredictable bounce-back season thus far – Gold Glover Brenton Doyle, and even veteran left-hander and hometown hero Kyle Freeland could potentially be former Rockies.

Whether this sort of thing actually happens is up to the players, in large part. They have to continue to produce and show they could help a contender if they’re going to be used as trade bait and want to play for a contender. And it’s a good bet that this front office will not let an abundance of loyalty get in the way of making a good deal to help build for the future.

The case of Freeland is especially tough. He’s been a solid member of the organization since he first arrived in 2017. While his stats aren’t all that great, especially recently, any scout worth his weight can see that a Freeland could provide a great boost to a contending team that needs left-handed pitching help. That includes a whole lot of teams.

For his part, Freeland has dismissed all trade talk in the past. He wants to remain a Rockie for his entire career, like Todd Helton and Charlie Blackmon. He probably closes his eyes and sees his retired number up on the wall above the Rockies’ bullpen. Still, he has to know that reaching the postseason while wearing purple pinstripes is the longest of long shots for the remainder of his career, so it sure looks like he’d rather stay put and try to help right this ship before he hangs it up than become a passenger on a different one, even if that one is destined for the playoffs.

On one hand, that’s very admirable. Loyalty to something other than the highest paycheck is a rarity for professional athletes these days. Kyle grew up a Rockies fan, and undoubtedly will remain one well into his golden years. In a perfect world, Kyle would end up with a World Series ring at some point. Heaven knows he’s toiled long enough to have earned one. But they don’t give those out for loyalty – you’ve got to play on a winner.

You have to wonder if Paul DePodesta and Josh Byrnes view loyalty the same way their owner does; might they be a bit more pragmatic about it? The question is whether they can convince Dick Monfort and Kyle Freeland that trading the veteran lefty to a contender this summer could be best for all involved. It would be best for Kyle – he’d get a shot at the World Series, perhaps – and he’d be helping the Rockies by allowing them to acquire more badly needed prospects to build with.

Maybe a team like the New York Yankees – a frequent trade partner with Colorado over the past year – would part with yet another top prospect in return for Freeland’s services down the stretch? Kyle could be a contributor to a playoff team – maybe even get a ring – and when the time came, he could return to Colorado to finish his career and later make the smooth transition to Special Assistant to the General Manager or some other nice front-office title.

That’s actually how loyalty to an organization is repaid. It’s not always about a guy’s playing days. It could be about the former player/person, armed with a great deal of baseball experience to share, could lend his help to the next generation of Rockies players.

Kyle Freeland wants more than anything for the Rockies to become winners again. He could help in more ways than just pitching for them.

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