Who would sign in Pittsburgh? – Hacker Perspectives

We are getting closer to the official end of the MLB season and the opening of Free Agency.

One of the hottest talking points is, “Who would want to sign in Pittsburgh?”

Let’s break down what Pirates has to offer players and what it doesn’t.


When Jarrod Dyson signed with the Pittsburgh Pirates in February 2020, he was pretty straightforward with his answer why he signed in Pittsburgh:

“There’s not much going on right now,” Dyson replied when asked why he signed with the Pirates. “You’d like to explore, but at the same time you have to take what you can, take the good with the bad and roll with it. Make the most of it.”

This touches on one of the earliest aspects of playing time. This would be an area for a player who may be looking to bounce back from the season. Recent positive examples include Tyler Anderson, Jose Quintana and Daniel Vogelbach. Anderson and Quintana both had histories of productive big leaguers at some point in their careers, while Vogelbach was someone who was mostly undersub throughout his career.

A team like the Pirates, in its current state, offers the opportunity for a player to receive an immediate starting position, as opposed to a player having to fight for a spot on the opening day roster. There can be a positional player that teams offer a bench or squad role to which the Pirates can step in and say, “We’ve got first base wide open and that’s yours.” Let’s say there’s a starting pitcher who’s been struggling recently and teams are looking at them as a bullpen option. The Pirates may offer the opportunity for a rotational starting spot.


It’s pretty self-explanatory. Free agents want to be paid.

Without it falling into the abyss of arguments over parity and the depth of such an owner’s pockets, the Pirates could probably take a shot at a top-tier free agent. This is highly unlikely for a myriad of reasons (apologies if you want to use that term).

Jon Gray, for example, signed with the Texas Rangers in the 2021 offseason for four years and $56 million. I think it’s easily a contract the Pirates could afford. All things being equal, if Gray had a choice between Pittsburgh and Texas on the same contract, I would have to imagine he chooses Texas, unless he secretly really likes bridges.

As things stand, Pittsburgh probably isn’t a desirable location until they do. In the hypothetical scenario, would offering Gray an extra million a year win his favor? Should it have offered $64 million or maybe just an extra year? We are not in the room and it is difficult to know exactly what it may take. Someone like Gray might want to sign closer to home – he’s from Oklahoma – which plays a role (wanting to be closer to home is at least mentioned in the rumors for some players).

Andrew Heaney had a tough 2021 season and followed it up with an effective but injury-plagued 2022. He’s someone the Pirates could potentially outbid other teams by offering a longer contract term.


Players with multiple suitors will likely prioritize winning. Whether it’s a team that has recently shown success or is showing signs of life to enter its “window” of success. The latter is the area I think the Pirates should focus on. This is an area where the front office becomes sellers and has to present its vision to free agents.

In 2021, the Detroit Tigers were coming off their fifth consecutive losing season. Their team wasn’t good, but they had a trio of intriguing arms coming out of their first extended look: Casey Mize, Tarik Skubal, and Matt Manning. The excitement for their position players was Rule 5 pick Akil Baddoo, and the Tigers also had one of the best farming systems in the league with two of the top five prospects in all of baseball: Spencer Torkelson and Riley Greene.

One of the biggest moves, in my opinion, was extending Jonathan Schoop in August 2021. At this point, Schoop wasn’t his 2016 or 2017 form, but he was a steady veteran. It’s not a splatter motion by any means, but that’s the look it gave off. In November, the Tigers traded veteran receiver Tucker Barnhart to split time with Eric Haase.

The Tigers’ first big move was to sign free agent Eduardo Rodriguez – who was screened by MLB Trade Rumors receive five years and $70 million – to a five-year contract that maxed out at $80 million. Then Javier Baez signed a big six-year, $140 million deal, which is highly unlikely for the Pirates. We could explain what happened next with Baez and Rodriguez falling short of expectations, Torkelson struggling and the Tigers having a worse 2022 season than 2021, but the Pirates eventually have to take risks.

put it all together

I want to highlight everything that led to the signing of Eduardo Rodriguez by the Detroit Tigers. By then, Miguel Cabrera had become a very, very expensive paperweight. Detroit is far from a desirable destination. They were a “losing franchise”.

As I said before, I believe the Pirates have the makings of an average league rotation starting with Mitch Keller, JT Brubaker and Roansy Contreras. They have quality veteran players in Bryan Reynolds and Ke’Bryan Hayes. They have one of the most exciting (if still raw) young players in baseball in Oneil Cruz. The farming system is going to have a plethora of top tier talent coming into the 2023 season.

Sell ​​free agents on this vision. Sell ​​them on the idea that they could be part of something bigger, on growth. Make an early trade or signing that shows they’re serious about transitioning out of their eternal rebuild.

Are Quintana and Roberto Perez serious about their return? Sign at least one, quickly. A respected veteran showing a desire to play in Pittsburgh would be a positive influence. Make a needle move swap that may have been discussed at the deadline packing some higher level prospects.

The longer the front office waits, the less likely there is to bring in potentially quality free agents. The longer they wait, the less likely they are to build a more competent roster.