When Might the Pirates Be Good Again?

The Pirates, in the midst of a woeful, 61-win-pace campaign, had two players start last night’s All-Star Game.

That’s a good sign for Pittsburgh.

One of the two, Adam Frazier, is only under club control for one more season, which is why he’s grown into an attractive trade deadline target among contenders. The other, Bryan Reynolds, is 26 years old, 28th in the majors in fWAR, has an xwOBA only four points off of his wOBA, and hasn’t even hit arbitration yet, which means he won’t be a free agent until probably 2025-26 (I’m not sure his Super Two status is locked in stone, but if it isn’t, it’s nearly locked in stone). Add to that Ke’Bryan Hayes’s pre-arbitration status (free agent in the 2026-27 offseason) and the Pirates’ farm system designation as, per FanGraphs, the third-most-valuable in baseball, and you might see where this is going: The rush of 2013-15 might soon return to PNC Park.

The question, of course, is when, though to be fair, there’s always a lot that could go wrong. Farm systems don’t just pop out major-league contributors on schedule, as advertised. There’s development involved, and there’s luck involved, both in the realms of health and talent. If you want Reynolds to be a part of it, 2025 is the back end of the window, so let’s establish that first. You have until 2025. So how soon can you contend?

Looking at the top names in the farm system, a deep group without an elite guy at the head (Quinn Priester, ranked 43rd by FanGraphs, is the team’s best prospect but isn’t quite 21 and as such holds some sizable risk down in high-A), and adding in Henry Davis, the first overall pick, you wind up with a pair of pitchers who could debut late this year (84th-ranked Roansy Contreras, 104th-ranked Miguel Yajure), a pair of infielders who could debut next year (92nd-ranked Oneil Cruz, 99th-ranked Liover Peguero), an outfielder who could debut next year (110th-ranked Travis Swaggerty), another starting pitcher who could debut next year (88th-ranked Tahnaj Thomas), two more position players who could debut in 2023 (Davis, 68th-ranked Nick Gonzales), and Priester, whose ETA is listed as 2024.

Now. With the exceptions of Gonzales, Yajure, Swaggerty, and Davis, all those players are high-risk prospects. The four listed who aren’t high-risk prospects are medium-risk prospects. The farm system holds no sure things. But again, as far as such things go, the majors already hold a pair of rather certain bets.

The 2015 Pirates had fifteen players contribute 1.0 fWAR or more apiece, averaging 2.9 apiece between them. It’s not a bad bet to say that Hayes, Reynolds, Jacob Stallings, and scuffling-but-promising Cole Tucker could be four of a parallel fifteen come 2023. Of the eight guys listed above who aren’t Priester, it’s fair to guess at least three could make up part of that sort of core as well. Say you get even just one from the depth part of the farm system, which is a cautious estimate. You’re then seven players away, with two trade deadlines as sellers, two free agency go-rounds, and a trade deadline as a buyer to try to complete the set. Between Adam Frazier, Richard Rodríguez (who the Pirates should absolutely trade, given he’s under club control through ’23 and relievers don’t always hold up well over time), and Tyler Anderson, it’s not outrageous to think the Pirates could bring back enough capital to get two more of those eventual core folks in the fold by the end of this month.

Would the window be open in 2023? Maybe not. But it would be opening, and back to the back end of it, even with Reynolds likely gone after ’25 in the best-case for the Pirates (which is that he plays himself into a big free agent deal), he and Stallings would be the only ones absent in 2026 in this scenario.

The big question is going to be the pitching. It hurts to not have a single guy about whom you can say, “That guy’s going to be part of the eventual contention rotation.” JT Brubaker’s the closest, but he’s still a ways from being proven and he’s only on track for a little more than 1.0 fWAR this year. Steven Brault is under club control through 2023, but last year was a small sample size and he’s yet to appear this season. Priester probably isn’t that guy yet, and would be coming into his own midway through the window anyway. Mitch Keller might be, but he’s past 100 major-league innings now and his ERA’s above 6.00, with a rough FIP since the beginning of last year as well. Yajure might be, but he still carries a lot of risk, even having made two spot starts this spring.

Should the Pirates target pitching prospects at the deadline, then? Maybe. They did add a few pieces of starting pitching depth to their farm system in the draft, but both are young. On the one hand, they’re far enough away from their window that they can probably still pursue the best overall players and work it out from there, but on the other, free agency’s a hard place to get reliable starting pitching. We’ll see. We’ll see, too, who all they trade away. Beyond Frazier, Rodríguez, and Anderson, there aren’t many guys who’d fetch a great haul, though Frazier’s return alone might include another top-100 prospect.

Ben Cherington’s built a World Series champion before, or at least built part of one. You can debate how much of the Red Sox’ 2013 success was thanks to him, how much was thanks to Theo Epstein before him, and how much came from outside of those two men, but he himself is something of a high-upside play as a general manager, with lots of love being sent his way after the draft this week, in which in the Pirates appear to have found some creative ways to maximize their bonus pool, selecting four of Baseball America’s top 32 prospects with their first four picks. As I mentioned earlier, things can always go wrong. But in the mire that is the NL Central (outside of the Brewers’ rotation), the Pirates might just be a couple years from rising back up to breathe.

The Barking Crow's resident numbers man. Was asked to do NIT Bracketology in 2018 and never looked back. Fields inquiries on Twitter: @joestunardi.
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