Mile High Sports

Strike 2: Union rep Kyle Freeland’s about to be stuck between a Rockie and a hard place

Sep 27, 2025; San Francisco, California, USA; Colorado Rockies starting pitcher Kyle Freeland (21) delivers a pitch against the San Francisco Giants during the second inning at Oracle Park. Mandatory Credit: D. Ross Cameron-Imagn Images

Right now, there’s a great vibe at Salt River Field surrounding the future of the Colorado Rockies. All signs are pointing up. In fact, there’s a lot of momentum for Major League Baseball in general, coming off a thrilling World Series and outstanding attendance and TV viewership numbers from last season.

Plus, the upcoming World Baseball Classic – the latest “US vs. The World” competition – promises to be exciting, providing American fans with another opportunity to puff out our collective chests.

Of course, all of this may come crashing down after this season, when the current Collective Bargaining Agreement expires and a pending work stoppage – a lockout of the players by the owners – ensues. Make no mistake, the 2027 season is in jeopardy.

There’s a growing disparity between the “haves” and the (relatively speaking) “have nots” in MLB in terms of revenue. The smaller-market teams can’t really compete for top-tier players, salary-wise, and it feels like those small-market clubs have virtually no chance at winning the World Series. That’s because the big, bad (and filthy rich) Los Angeles Dodgers have all the money and a stacked roster. It’s “time for a salary cap” is the current cry among fans, media and some of – but certainly not all of – the owners.

Rockies owner Dick Monfort is among the principal mid- and small-market owners pushing for a cap in a game that has never had one. His team’s MLBPA rep is left-hander Kyle Freeland, the Denver native and favorite son. The players’ union is steadfast against any sort of cap for obvious reasons. Monfort and the other group of owners who are pushing for a cap believe it will give them a better chance to compete with the Dodgers, Yankees, etc. (Hint: it wouldn’t.)

For as good a person as Kyle Freeland is, he’s about to get caught between the Rockies and a hard place, because this could get a little nasty.

A salary cap – and an accompanying salary floor – likely won’t help the Colorado Rockies much, especially over those next two seasons when Kris Bryant’s albatross of a contract for $27 million per remains on the books. The only thing that could help the Rockies – and other smaller-market teams – would be greatly enhanced revenue sharing among the owners – specifically involving local media rights revenue. Right now, the Dodgers are set to receive $334 million for their local TV rights, while the Rockies are now part of ESPN’s stewardship of their local broadcasts. So technically, the Rockies don’t have any local TV revenue anymore.

Fix that revenue discrepancy and you finally level the playing field… without any need for a salary cap.

What this dispute really comes down to is owner vs. owner.

When negotiations intensify after this season ends, Freeland will be listening to the union’s stable of lawyers and economists, who will report on how much the game is making, how it’s grown, and what great shape it’s in. He’s going to leave those meetings wondering why his owner is crying that he’s poor and wants to hold down player salaries. While I have no doubt that the current relationship between Freeland and Monfort is solid, there will be a strain put on that relationship. Could that strain be relationship-ending?

Will Freeland still be a Colorado Rockie when the 2027 season finally begins?

Perhaps. Back in the day, Milwaukee Brewers owner Bud Selig had a father-son relationship with his third baseman, future Hall-of-Famer Paul Molitor. When Bud was elevated to the commissioner’s chair, Paul was the American League’s player rep. The pair sat across the negotiating table from one another. There were strikes and lockouts during their tenure. Yet somehow, some way, they stayed friendly and made it work. Some even believe that their relationship helped end some labor disputes – much like the one that’s upcoming.

On the flip side, it hasn’t been uncommon for a team’s player rep, someone who may have been “outspoken” during the work stoppage, to not be welcomed back after a new agreement has finally been reached. The Rockies banished former starting catcher Joe Girardi – a vocal and prominent member of the union during the players’ strike of 1994-95 – by trading him to the New York Yankees after the 1995 season.

So when next December arrives, and the owners and players are dug in on their respective bargaining positions, will Freeland and Monfort, sitting on opposite sides of the table – be able to help work things out… or will Kyle be a former Rockie by then?

Rockies fans – and baseball fans in general – should be hoping that the relationship between Kyle Freeland and Dick Monfort can remain positive enough to be part of the solution next winter, and not part of the problem.

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