Pittsburgh Pirates: Ben Cherington's Most Important Draft

Ben Cherington took over as the Pittsburgh Pirates general manager right as the team's rebuild was beginning. Of his four drafts, which one is the most important to the rebuild?

When a team rebuilds, the draft is arguably the most important event. The trade deadline and international signing period can both build up a team’s farm system, but the draft is an easy way for a team to add multiple top prospects all at once. The Pittsburgh Pirates have been rebuilding since the conclusion of the 2019 season, and they’ve gone through four drafts under Ben Cherington. But among these four, which is the most important?

Before we get into it, I want to first state that there's no such thing as an unimportant draft. Every draft holds significance. But some drafts hold more significance than others, especially when a team is rebuilding. Every draft gets a team a top prospect, but not every draft gets a team multiple high-end players.

I think it’s safe to say that the 2020 draft was the ‘least’ important. That’s not to say that it wasn’t important, but given the context of the draft, it probably holds the least significance of the Pirates’ four rebuilding drafts. The draft was only five rounds because of COVID. None of the prospects any team drafted got a proper year of development.

The Pirates did manage to get a couple of decent prospects. Nick Gonzales and Carmen Mlodzinski made their big league debuts this year, and Jared Jones has developed into one of minor league baseball’s better pitching prospects. But given the draft was just five rounds, the Pirates only had so much they could work with.

In terms of which draft got them the best prospect, it would easily be this year’s draft, 2023. The Pirates had the number one overall selection and took Louisiana State University right-hander Paul Skenes with the pick. Skenes is easily the most hyped draft prospect since Stephen Strasburg, if not ever. The flamethrowing right-hander had a microscopic 1.69 ERA and 0.75 WHIP through 122.2 innings for LSU. This also included an insane 45.2% strikeout rate, 4.3% walk rate, and 0.51 HR/9 rate.

Skenes set the all-time signing bonus record, inking his deal for $9.2 million. The Pirates did get some decent talent later in the draft, such as Mitch Jebb and Zander Mueth. They also took some low-floor/high-ceiling pitchers in the form of Patrick Reilly, Magdiel Cotto, and Carlson Reed.

Plus, late-round pick Charles McAdoo has looked great so far. But Skenes is far and away the best talent they got, and nobody even comes close in comparison. The Pirates took a risk/reward approach on this draft after Skenes, which could pay off in the long run, but they certainly are far from guarantees.

Because of that, I can’t say that this draft is the most important. Again, that doesn’t mean that this wasn’t an important draft, but since Ben Cherington took over, and based on what the Pirates did and the timing of the draft, this wasn’t the most important one of the rebuild yet. So that leaves just 2022 and 2021.

So what about last year’s draft? The Pirates certainly got some very good talent in this one. Termarr Johnson is one of minor league baseball’s best prospects. Thomas Harrington, their first-round competitive balance pick, has also been trending upward.

Second-rounder Hunter Barco has done well since returning from Tommy John surgery, and both Jack Brannigan and Tres Gonzalez have done great despite not being considered high-end draft picks. Plus, high school 4th rounder Michael Kennedy has been fantastic this year at the Pirates’ Florida Complex League affiliate. He recently got moved to Low-A Bradenton in just his age-18 campaign.

For most teams, that might constitute the best and most important draft of a rebuild. But with how the Pirates handled the 2021 draft, it has to be the most important one yet. The Pirates got three first-round picks with their first four selections. The 3rd pick is doing exceptionally well and might eventually become a top-100 prospect. Not only is this draft the most important in the rebuild, but it has the potential to be the Pirates’ best-ever draft.

With the number one overall pick, the Pirates took catcher Henry Davis out of the University of Louisville. Then in the second round, they took high school lefty Anthony Solometo, who had the best command out of nearly every other draft-eligible pitcher. Lonnie White Jr. was the team’s second-round competitive balance pick. In the third round, the Pirates took their third high school player in a row in Bubba Chandler. Davis was considered one of the best prospects in the draft, but Chandler and Solometo were projected to go within the back-half of the first round.

These weren’t even the last of the Pirates’ noteworthy picks. Owen Kellington, Sean Sullivan, Jackson Glenn, Tyler Samaniego, and Braylon Bishop have all shown the potential in the minor leagues to give the Pirates something in the future. Of course, it’s unreasonable to expect the Pirates (or any team, for that matter) to hit on every single one of their draft picks. But this one gave the Pirates’ system the boost it needed and propelled it into one of the best systems in the sport.

While it might take another year or two to potentially see the full potential of what some of these drafts will hold, they’ve already started to bear fruit. Guys like Gonzales, Mlodzinski, and Davis have already made their debuts. But many others like Chandler, Harrington, Solometo, Jones, and even their most recent first-round pick, Paul Skenes, could all debut next season.