The Colorado Rockies are heading into free agency with pitching at the top of the wish list, and the first name that makes sense is Jack Flaherty.
Colorado needs arms, especially a left-hander, but the case here is for the right-hander who just finished a rough 2026 season. Flaherty went 3-8 with a 4.48 ERA and 103 strikeouts, numbers that don’t jump off the page at first glance. Still, there’s more to the fit than one down year.
Flaherty brings October experience with him, having pitched in the playoffs for both the Detroit Tigers and the Los Angeles Dodgers. He also owns a World Series ring after the Dodgers beat the New York Yankees in five games in 2024, a season in which he won 13 games.
The appeal for Colorado is that Flaherty still looks like a pitcher who can give you real value. He has seven seasons with 100 or more strikeouts, plus one season with more than 200. He also has a reputation for mental toughness, the kind of presence that doesn’t flinch after a bad outing and keeps looking for ways to improve.
When his curveball and slider are working and he’s spotting the ball well, hitters can have a long night. That’s the version the Rockies would be betting on. He may not be the flashiest option on the market, especially next to a name like Tarik Skubal, but he is available, and Colorado has to be willing to take some swings if it wants to change the direction of the roster.
There also isn’t a deep pool of pitchers in their 20s in this free-agent class. Flaherty, now 31, is still viewed as being in the prime of his career, which gives the Rockies a chance to land someone who could pay off if he bounces back in 2027.
The winter meetings are always a crowded marketplace, and this one figures to be no different. Teams will be fighting over the same players, and the money will get loud fast. Not every club will have the flexibility to chase the biggest names, but Paul DePodesta and the Rockies’ front office could still make a pitch if they can sell the organization’s future.
And that’s part of the equation too. It’s not just about the paycheck.
It’s about the person, the leadership, and how the team presents itself when it sits down to make its case. Eye contact, good direction, and high road leadership matter a lot.
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