Extending a Player or Two Makes Sense for the Pirates, but Who?

Everyone is waiting to see what moves the Pirates will make this offseason. The most obvious reason is to see what the 2021 version of the club looks like, but for me it’s more so about further understanding Ben Cherington’s approach.

We talk about trade possibilities and who might not be offered a tender. We discuss potential free agent signings who rarely move the needle and more than anything we talk about the low value many Bucco’s assets have on the market. One area we don’t touch on often is the possibility that they Pirates could, and probably should extend a player or two, in order to both lock in some continuity, but also to give the fans a bit of belief that spending as little as possible won’t be the plan forever.

Today, let’s look at some candidates and discuss the likelihood that the Bucs could extend any of them.

Josh Bell

Let’s start big, and controversial. Trading Josh is a problem, his value isn’t at a level where the return would make sense. Extending Josh is at least a perceived problem because Scott Boras is his agent.

That’s part of the story, the other part is more painful to discuss. Is Bell good enough to sign for more years? For instance, if you knew how Gregory Polanco would turn out, you never sign him for all those years and certainly not that amount of money. If you extend Bell, sure you hope he comes into his own and improvement certainly isn’t out of the question, but this can’t be done out of pure vision of potential. To a certain degree he is what he is.

Now what is he? Well, he’s a streaky power hitter who sometimes is going to put it together and dominate stretches of your season and other times make you consider batting him 7th or benching him. He’s going to top out at passible defensively, and I don’t think he’s quite to that level yet.

All that being said, both team and player have expressed interest in extension and that’s more than I can say for any other player on the team so to not include him in this look would be wrong.

If this happens, in my mind, this is a short extension. I’d think both team and Boras could benefit from buying a bit of time here to build value or at least give time to breathe, a year or two max.

Ke’Bryan Hayes

My partner Craig brought this one up before Hayes even made his debut, no doubt inspired by how the White Sox handled Luis Robert, but this isn’t a crazy idea. Sure Hayes has plenty of time left to show who he is but the Pirates have to take risks sometimes along these lines in an effort to keep costs in control.

It’s a risk, and right now both sides would use his cup of coffee to build it out. Hayes and the Pirates both know he isn’t a .370 hitter, but the facts are the facts, he did exactly that in his debut. Perhaps approaching him now wouldn’t be best for business but it sure would make some fans believe.

Hayes could accept a little less later for a little more now, so if you went say 8 years you could make this work and buy out his arbitration plus a year or two. If nothing else you lock up a sure fire defensively phenomenal third baseman and with little else in the pipeline at the position, give yourself one place to call your anchor.

Bryan Reynolds

Bryan is coming off the single worst season he’s ever played. I find it incredibly hard to believe those 60 games represent who he is and a smart front office should feel the same. He’s got the potential to be the quiet compass of the team and now is the time if you want to get this done affordably, because again, I can’t see him struggling like that again.

Last season he showed a set of tools none of us knew he had in the outfield gunning down runners who didn’t benefit from accurate scouting reports about his arm. He can play center, although I still feel left is best for him, but the ability doesn’t hurt his value.

If you want a face of the franchise, Bryan is gonna do it on the field rather than his voice, but that quiet confidence and understated leadership really plays.

He’s still pre-arbitration and doesn’t become a free agent until 2025 but I firmly believe by then this isn’t a guy the Pirates will regret not extending if they pass on the chance. He’s an easy lock up through 2027 or 28 and that eclipses the entire projected window.

In my mind, and out of everyone on the club, Bryan is my first call on this topic.

Joe Musgrove

Joe’s not a star, I don’t even think he profiles as one. His stuff is really good and I think he’ll settle in as a top third starter. Let me clarify, I don’t mean top third of this team, I mean the league, and keep in mind that’s hundreds of pitchers that create that pool.

The Pirates have some really interesting and talented young pitching in the system but we all should have learned that expecting them all to progress, stay healthy and arrive together is the longest of long shots. Even if you prematurely add Rocker to the mix, asking 3 or 4 young pitchers to stay on schedule with no hiccups to produce at playoff team level by any date you can pick out of the air is a dangerous game.

Joe is a perfect player to think about keeping as an anchor for the rotation. He won’t break the bank, he’ll give you solid pitching more often than not and if he ends up being your number 4 or 5 he won’t become a locker room problem because he was never under the delusion he needed to be more.

The locker room loves the guy and so do the people who pull the trigger on stuff like this. He’s a free agent in 2023, so for Joe, this very much so is a get it done now or move him situation.

Mitch Keller

Mitch is much along the same lines as Hayes, but he is someone a team like Pittsburgh should consider extending because of where he is in relation to the other young pitchers in the system. See by the time they get here (well some of them as we discussed) Keller will have put in a solid 2 or 3 cumulative seasons. With free agency projected for 2026 they certainly have time but if the window opens when many of us think it should the Bucs could also be dealing with having to either move him in the middle of the window or trying to pay him far more than he’d be able to negotiate today.

A common theme with many of these has been for the Pirates to take a risk, but this is very much so what teams like Oakland or Tampa do regularly. With Mitch, you aren’t buying what he is now, you’re buying what he could be and potentially avoiding dealing your club a huge blow right when things start taking shape.

Jameson Taillon

Jameson is a risk too, clearly. He’s been injured more than most MMA fighters and at the end of the day the best ability anyone has to offer is availability.

Jamo will be a free agent in 2023 and I’d never suggest this before seeing how he comes back from his second TJ, but much like Musgrove, this might be a veteran worth taking a swing on. His injury history could keep him affordable and if the bet plays you got yourself a pitcher who can settle in the top half of your rotation, if it fails, you might have an expensive bullpen arm or he just retires of his own volition.

In Closing

I’m sure there are others and I’d love to hear your ideas, but these would be my top targets. I think they can get these done adding minimally to the payroll for years, let alone this year and I’m also not suggesting they go and extend ALL these guys.

Keeping your own is something that helps build credibility with a fan base and more importantly, keeps you from being in a constant state of the roster being on the same exact timeline. If the goal is to open a window and keep it open, which is certainly should be, then you have to start to create a staggered construction.

The only way to fix the mess that was created is to work on skewing the picture. There is a difference between trade value and extension value in baseball, I fully expect the Pirates to explore the latter.