First Pitch: When Does the Window Open Back Up?

I don’t think anything significant is going to change in baseball over the next Collective Bargaining Agreement, at least in terms of the advantage that large market teams have.

What that means is that teams like the Pirates will still have to rely heavily on developing their own stars, rather than signing them via free agency or trading prospects for established guys who are still at the height of their careers.

It also means prospects like Ke’Bryan Hayes and Mitch Keller probably won’t spend their full six years of service time in Pittsburgh, unless they sign extensions. Even if that happens, they’ll likely be moved before the extensions expire, as we saw with Starling Marte prior to this season.

I bring this up because while looking at sleepers on the Pirates’ roster, Joe Musgrove is always a guy who stands out. The problem is that Musgrove is only under team control through the 2022 season. The Pirates are unlikely to win in 2021, and if Musgrove has a breakout season, they’d be better in the long-term trading him at a high value, rather than keeping him to contend in 2022. Even if Musgrove has upside, he’s unlikely to help the next winning Pirates team.

If we move beyond Musgrove, we start to see a window forming with the current prospects. Hayes is under control through 2026, assuming he stays up for good. Mitch Keller is under control through 2025, joining Bryan Reynolds and Kevin Newman.

If we assume that these guys will be traded within two years of free agency, and we assume 2021 won’t be a contending season, that leaves 2022-2023 as the years to contend with Keller, Reynolds, and Newman, extending to 2024 for Hayes. Of course, there’s no rule saying these players need to be traded by that time frame, and the Pirates have kept players until right before their final year of team control. That still leaves a 2022-24 window, extending to 2025 for Hayes.

The Pirates have some prospects who could arrive during this time to help, but they’re also going to need help from the outside, just as the 2013-15 team received with the additions of guys like A.J. Burnett, Russell Martin, and Francisco Liriano.

I’ll dig into some of the prospects who could arrive to help in tomorrow’s article. Today’s discussion question: When do you see the Pirates window of being a contender again?

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First Pitch