Welcome back to the 2026 MLB Front Office Rankings. If you missed them, you can catch up on the first two articles here:

Part 1: Introduction
Part 2: Teams 30-21

TIER 5: YOU ARE THE ONLY EXCEPTION

20.) Pittsburgh Pirates
General Manager: Ben Cherington

This tier comprises some of the absolute toughest organizations to balance: teams which do some things really, really well but have major flaws in their overall operational structure. These flaws have either prevented lengthy contention cycles or are likely to do so in the near future.

The Pirates have one of the best pitching development track records of the decade, something which is fairly recent; as recently as the Cole/Glasnow era they were a popular target for teams to snatch talented pitchers from, because they were usually poorly optimized. These days, they tend to collect whiffy traits in the draft and design diversified arsenals, producing the core of a homegrown rotation of guys in their mid-20s who look like current or potential top-of-the-rotation starters. Seth Hernandez might yet be the best of them all—he certainly has the whiffiest traits of any pitching prospect in a hot minute—and he still hasn’t landed yet. This has started to extend to their pro acquisition moves too, particularly in the bullpen, where they’ve gotten huge gains out of similar poor command stuff monsters like Mason Montgomery and Gregory Soto.

Their hitting development and acquisition record is, generously, a mixed bag. It’s certainly a directional win that Konnor Griffin popped so quickly in pro ball for them, but at the same time he hasn’t really looked ready to excel in the majors since his promotion. They’ve had a number of high-profile developmental misses, although retrospectively it does seem like 2021 was a historically terrible 2016-level top of the draft and that they wouldn’t have really been any better off taking Jack Leiter or Marcelo Mayer instead of Henry Davis. But it’s on them some, too. They don’t select well for hit tools in amateur or pro scouting and don’t squeeze improvement out of guys who need contact and swing decision improvements—a long way of saying Oneil Cruz should be so much better than he is—which might be a hidden flag for Griffin and other damage-heavy top prospects in the system like Edward Florentino and Axiel Plaz.

Their major-league free agent and big-money trade moves are nearly non-existent, which is obviously an ownership choice by the widely maligned Bob Nutting. They tend to spend on defensively limited bats and mid-rotation pitchers when they do venture out into the market, which isn’t really optimal or creative with limited funds, but at least they make some decent choices within sub-optimal acquisition strategies. As mentioned, Soto was a great signing this past offseason, and Brandon Lowe and Ryan O’Hearn have lived up to expectations.