Pirates Weekly Discussion: Who Would Sign in Pittsburgh?

We’re inching closer to the official end of the MLB season and the opening of Free Agency.

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

Let’s break down what the Pirates have to offer to players, and what they don’t.

Playing Time

When Jarrod Dyson signed with the Pittsburgh Pirates in February of 2020, he was pretty blunt with his response on why he signed in Pittsburgh:

“Ain’t too much out there right now,” Dyson replied when asked why he signed with the Pirates. “You would love 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 first aspects of playing time. It would be an area for a player that may be looking to have a bounce back season. Some recent positive examples would include Tyler Anderson, Jose Quintana, and Daniel Vogelbach. Anderson and Quintana both had track records of being productive big leaguers at one point in their careers, whereas Vogelbach was someone who was mostly sub-replacement over the course of his career.

A team like the Pirates, as they stand, offer the ability for a player to receive an immediate starting position as opposed to a player having to battle for a spot on the opening day roster. There may be a position player that teams are offering a bench or platoon role to that the Pirates can step in and say, “We have first base wide open and it’s yours”. Say there is a starting pitcher that had recent struggles and teams are considering them as a bullpen option. The Pirates can give the opportunity for a starting rotation spot.


This is rather self explanatory. Free Agents want to get paid.

Without this falling into the abyss of arguments over parity and the depth of one such owner’s pockets, the Pirates probably could take a shot at a higher tiered free agent. That is very unlikely for a myriad of reasons (excuses if you want to use that term).

Jon Gray, as an example, signed with the Texas Rangers in the 2021 off-season for four years and $56 million. I feel that’s easily a contract the Pirates could afford. All things equal, if Gray had the choice between Pittsburgh and Texas on the same contract, I would have to imagine he chooses Texas, unless he secretly really loves bridges.

As it stands, Pittsburgh isn’t likely a desirable location until they make it so. In the hypothetical scenario, would offering Gray an extra million per year gain his favor? Would it have taken offering $64 million or maybe just an additional year? We’re not in the room and it’s hard to know what it may exactly take. Someone like Gray may 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 rumors for some players).

Andrew Heaney had a rough 2021 season, and followed it up with an effective but injury-plagued 2022. He is someone the Pirates could potentially outbid other teams by offering a longer length of contract.


Players with multiple suitors are likely to prioritize winning. Whether that is a team that’s recently shown success, or is showing signs of life into entering their “window” of success. The latter is the area I believe the Pirates should be focusing on. It’s an area where the front office becomes salesmen and need to pitch free agents on their vision.

In 2021 the Detroit Tigers were coming off of their fifth straight losing season. Their team was not good, but they had a trio of intriguing arms coming off 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 top farm systems in the league with two 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 of 2021. At this point, Schoop wasn’t his 2016 or 2017 form, but he was a stable veteran. It isn’t a splash move by any means, but it’s the appearance it gave off. In November the Tigers traded for veteran catcher Tucker Barnhart to timeshare with Eric Haase.

The first big move the Tigers made was signing free agent Eduardo Rodriguez — who was projected by MLB Trade Rumors to receive five years and $70M — to a five year deal that maxed out at $80M. Next was signing Javier Baez to a hefty six year $140M deal that is very unlikely for the Pirates to do. We could go into what happened thereafter with Baez and Rodriguez not living up to expectations, Torkelson struggling, and the Tigers having a worse 2022 season than 2021, but the Pirates have to take some risks eventually.

Putting It All Together

I want to emphasize everything that lead up to the point of the Detroit Tigers signing Eduardo Rodriguez. By that point, Miguel Cabrera had become a very, very expensive paper weight. Detroit is far from a desirable destination. They were a “loser franchise”.

As I’ve said before, I believe the Pirates have the makings of a league average rotation beginning with Mitch Keller, JT Brubaker, and Roansy Contreras. They have quality veteran players in Bryan Reynolds and Ke’Bryan Hayes. They have one of baseballs most exciting (if even still raw) young players in Oneil Cruz. The farm system is going to have a plethora of upper level talent entering the 2023 season.

Sell free agents on this vision. Sell them on the thought that they could be a piece in something bigger, on growth. Make an early trade or signing that shows they’re serious about transitioning out of their everlasting rebuild.

Are Quintana and Roberto Perez serious about returning? Sign at least one of them, quickly. A respected veteran showcasing a desire to play in Pittsburgh would be a positive influence. Make a needle moving trade that may have been discussed at the deadline by packaging some upper level prospects.

The longer the front office waits, the less of a chance of bringing in any potentially quality free agents. The longer they wait, the less of a chance they have of building a more competent roster.

Raised in Cranberry Twp, PA, Jeff attended Kent State University and worked in Cleveland and Pittsburgh, before moving to New Orleans in September of 2012. His background is as an Engineering Designer, but he has always had a near unhealthy passion for Pittsburgh sports. Hockey and Baseball are his 1A and 1B, combined with his mathematical background, it's led to Jeff's desire in diving into analytics. Jeff is known as Bucs'N'Pucks in the comments, and began writing for Pirates Prospects in 2022 after contributing so many useful bits of information in the comment section.

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