The First Free Agent Colorado Rockies Should Sign

The Colorado Rockies front office personnel will be working hard to make some free-agent signings.

Some big names are in this year's 2026 free-agent class. If there's one signing that the Rockies should get the ball rolling on, it would have to be pitching.

About Jack Flaherty

Detroit Tigers pitcher Jack Flaherty delivers the ball Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect

As much as Colorado needs a left-handed pitcher, the first free agent they should go after is right-handed pitcher Jack Flaherty. The 31-year-old is coming off a rough 2026 season, posting a 3-8 record with a 4.48 ERA and 103 strikeouts.

Why would the Rockies go after a pitcher with those numbers? Because coming to an organization like the Rockies can redeem his career. Also, he brings playoff experience to the team. Flaherty pitched in October with the Detroit Tigers and the Los Angeles Dodgers. Flaherty earned a World Series ring when the Dodgers won in 2024 after defeating the New York Yankees in five games. Flaherty won 13 games that year.

Flaherty is still capable of winning double-digit games. Flaherty has seven seasons with 100 or more strikeouts, and one season with more than 200. One of his greatest assets is his mental toughness. He doesn't have fear when he's on the mound. Flaherty doesn't stress about bad performances. He seeks ways to get better.

When he uses his curveball and slider and hits his spot in the strike zone, it can make for a complicated day for the hitter. The Rockies need this caliber pitcher on their roster. Flaherty may not be a top choice or a big name compared to Tarik Skubal, but he's available, and the Rockies have to take risks if they want to move the needle.

There are not too many pitchers in free agency who are in their 20s. The fact that Flaherty is in his early 30s, still considered to be in the prime of his career, can be a steal for the Rockies if he has a bounce-back 2027 campaign.

When it comes to free agency during winter meetings, the competition is at an all-time high. Every team is looking to get a piece of the pie. The contract offers will be through the roof. Not every team will be flexible enough financially to pursue a player, but if Paul DePodesta and the rest of the management can sell the free agent on their plans in the future, then they might get lucky.

It's not always about the money, but it can be about the person, the leadership, and how the organization presents itself during its presentation. Eye contact, good direction, and high road leadership matter a lot.

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