Pittsburgh Pirates: Looking at What the Offseason Could Hold

What kind of approach will the Pittsburgh Pirates take this offseason when it comes to adding to the Major League roster and the payroll?

The 2023-2024 offseason will be an extremely important one for the Pittsburgh Pirates. Not only will it be the most important one of the rebuild, but maybe the most important of the franchise’s most recent history. But how will the Pirates use their money this offseason? How will Ben Cherington spend what he has available to him?

Before the smart-alecks say “That’s easy, they won’t spend”, keep in mind the Pirates added about $30.5 million in payroll last off-season via free agent signings. That also doesn’t account for the $4.65 million they added with Ji-Man Choi’s contract, the $735,000 that Connor Joe brought alongside him, or the rookie minimum owed to Jose Hernandez. Once you account for these acquisitions, the Pirates added just over $36 million in Major League roster additions.

Also, keep in mind the Pirates’ free agent spending has gone up dramatically over the last few offseasons. In 2021-2022, the Pirates only spent about $16.3 million in free agent additions. The only Major League free agent they pursued in 2020-2021 was Tyler Anderson for just $2.5 million. I’m not saying the Pirates will nearly double their off-season spending again, and reach into the $60 million range this offseason, but it’s reasonable to expect and assume the Pirates to spend more than they did last year. It's not as if they haven't had a $100 million payroll in the past, and if there was any time better to spend that much, this offseason would be it.

The approach the Pirates took last offseason was more of the “safe” approach. The Pirates were essentially testing the waters this season, and last off-season reflected that. Every free agent signing the Pirates made was for just one year. The only one that wasn’t was Jarlin Garcia, who signed one year with a club option for 2024 (which will likely get turned down and save the team $3.5 million). Choi was also on just a one-year deal, with Joe and Dauri Moreta the only major additions that had control beyond 2023.

The Pirates really should take a different approach this upcoming winter. First, the team is in a much different position than in October of 2022. There’s much more riding on 2024 than there was in 2023. Instead of signing four or five low-cost, sub-$10 million AAV free agents, maybe go out and get two or three higher cost ones, alongside one or two mid-tier free agents.

As I’ve previously written about, the one thing this regime cannot do is what the last regime did, and that’s spending unwisely. In 2016, the Pirates had a payroll of just under $100 million. In 2017, their payroll was just over $100 million. So why didn’t it feel like they had a $100 million payroll for two years straight? It’s because most of their additions weren’t massively impactful. Their biggest free agent signing in 2015-2016 was Neftali Feliz, and their biggest addition the following offseason was Ivan Nova. These aren't the big moves you'd expect a team that is trying to reinforce a roster would make.

It’s not about how much is spent: it’s about how it’s spent. The Pirates this offseason need to take an aggressive, but smart approach. Go after higher priced free agents, but ones that will help improve the roster. Avoid making most of the off-season additions small-time one-year deals. There’s nothing wrong with making some of those signings, but don’t let them dominate the offseason.