Williams: The Pirates Need to Get Aggressive in Free Agency

The Pittsburgh Pirates have been in rebuild mode for seven seasons.

It hasn’t been called that once.

Neal Huntington was trying to contend until the very end in Pittsburgh. Ben Cherington took over as the General Manager prior to 2020, and insisted on a “build.”

You could make an argument that the Pirates didn’t have a sustainable approach when they made the playoffs under Huntington. You could also make an argument that they didn’t really have a good approach at all to making the playoffs.

What I’ve seen from this “build” is Cherington building something more sustainable for when the Pirates are contending again. He also has the challenge of actually getting them back to being contenders. That will simply involve bringing in better players.

There are three main avenues a small market team can use to bring in talent: the draft, trades, and free agency.

We’ve seen Cherington get aggressive with two of those approaches. At this stage in the process, it’s time for the Pirates to get aggressive in the third.

The Draft

There have been two full drafts from Ben Cherington so far, along with the abbreviated 2020 draft.

The 2021 draft was a monster, with the Pirates picking first overall and loading up the system with catcher Henry Davis and prep players Bubba Chandler, Anthony Solometo, Lonnie White Jr., Owen Kellington, and Braylon Bishop. This draft class was probably the biggest influx of talent into the system under Cherington, and could lead to multiple impact players in the majors.

The 2022 draft was a bit more of a normal draft. The Pirates landed the top pure hitter in Termarr Johnson, but didn’t have the overall depth impact after the first round when picking fourth overall. There were a lot of college players taken, so this draft could provide some players to get the Pirates back to contending again. This draft probably won’t really impact the Pirates until Johnson arrives.

The draft is always going to be the best place for the Pirates to find impact talent. However, that impact potential is limited and years away. The players from these early drafts might start arriving next year. It’s been early to evaluate the development process, but there have been some red flags with the struggles from Nick Gonzales.

At this stage, any new draft will extend the window for the Pirates. A college player drafted in the first round next year might arrive in 2025. A prep player would arrive later. There’s a chance that the 2020-2022 drafts could produce players who kick start the next contending Pirates team, but any draft going forward is about maintaining in a future where the Pirates need to be contending.

Trades

Who was your favorite trade deadline pickup? When we discussed the returns, there weren’t a lot of players to choose from.

Prospect Roundtable: Who Was Your Favorite Trade Deadline Acquisition?

If the Pirates are lucky, they can get one starter from this group. The more likely outcome is they get a few role players, with right-handed reliever Colin Holderman being the obvious top candidate to provide value.

The problem is that the Pirates aren’t “a few role players” away from contending. This team needs impact, and they’ve reached the point where they’re not going to get that on the trade front. The only way they could do that at this point would be trading Bryan Reynolds or David Bednar, with each move pushing them further away from contending in the short-term, all to strengthen a long-term that has no discernable beginning.

The trades we’ve seen so far have yet to play out, mostly due to a lack of time. Roansy Contreras, Endy Rodriguez, and Liover Peguero are three of the top young players in the system, acquired for the biggest trade chips that Ben Cherington had — Jameson Taillon, Joe Musgrove, and Starling Marte.

The Pirates have seen Wil Crowe and Bednar impact the majors from those moves. They’ve seen promise from guys like Jack Suwinski, Tucupita Marcano, and others acquired during the sell off. There are a lot of other wild card prospects from those deals.

This is where the development takes over and tries to turn those players into Major Leaguers. Those results are still up in the air. Right now, it doesn’t appear that there will be much talent entering the system through this avenue going forward.

Free Agency

The Baltimore Orioles recently made headlines when their General Manager, Mike Elias, said they would “significantly escalate their payroll” this offseason. Elias highlighted being aggressive in free agency and trading for players who have inflated contracts.

The Orioles are in a very similar situation to the Pirates. They actually opened the 2022 season with a lower payroll than Pittsburgh. Their payroll was close to $170 million in 2017, so they’re clearly in a slash-and-rebuild at this stage.

Ben Cherington seems to be following the same model for the Pirates.

One issue with that statement is the Pirates have always been a highly secretive organization. Logically, you can look at what the Pirates are doing and see they’re doing the same thing as the Orioles.

The difference is that I don’t think Ben Cherington is going to come out and say exactly how the Pirates plan to be aggressive, in the same way that Mike Elias did for the Orioles.

I grew up an Orioles fan, so I’m going to add the disclaimer that they aren’t, and never really have been a model organization. Just because their GM is public about their intentions doesn’t mean that Ben Cherington needs to be public about his intentions. He just needs to have the same intentions.

The biggest problem the Pirates have is a lack of transparency with their fans. I can tell you that I think this organization is going to do the same thing as the Orioles. As long as Bob Nutting owns this team, there will be serious doubts from fans over the team’s willingness to spend like a Major League team should. And even I wouldn’t predict that the Pirates would spend what the Orioles have spent, under Nutting.

There should be no doubt about what the Pirates need to do this offseason.

They are relying on the farm system for good reason right now — this team had too many holes to fill to just start spending money in free agency.

There are some obvious places where the Pirates need help in the majors, and can’t afford to rely on their minor league options. They need a first baseman, another late inning reliever, and at least one veteran starter.

Rebuilding through the draft and trades is Rebuilding 101. Anyone can trade a major league player and wind up with players to dream about for a future that might not come.

The Pirates have graduated from that entry-level course, and need to show at this stage what they can do to boost the rebuild via free agency.

I think that’s what Ben Cherington has been setting up all along.

Even if he’s not as open with his plans as other General Managers.