Pittsburgh Pirates trade deadline preview

The MLB trade deadline is fast approaching as we are now within three weeks to go until the big day on August 1. This is always an exciting time of year as we find out who is doing what and how the landscape of the league changes and the playoff picture comes into focus. 

The Pirates are in an interesting spot as they will come out of the break at 41-49 and 8 out of a wildcard spot and 8.5 out of the division lead. They have really faded since about the middle of June but since the big 20-8 start, they are just 21-41. This is hardly a team that looks like one that should be buyers this year. However, if they can somehow come out of the break hot for a week or so and maybe trim the deficit to 4 or 5 games, the outlook could perhaps change. 

However, even if they are sellers, which is what appears should happen, they seem to be past the point of the big sell offs in a rebuild kind of fashion. It is more likely they will just sell off short-term assets with no future on the team weather than any more big wholesale changes. All in all, this is a total preview of the kinds of players they could look to trade with the assumption they are sellers this month.

Andrew McCutchen:

McCutchen returning to Pittsburgh has been a jolt of energy to the team, even if they still lack the talent to compete just yet. His influence is still felt and his presence in Pittsburgh is felt too. The Pirates would be foolish to trade him despite it maybe being the best thing for them on paper. Cutch should remain a Pirate as long as he plays. The only thing that would change this is if he goes to the front office with a demand to go to a contender but I can’t imagine that given how much he’s stated he wants to be in Pittsburgh. I do not envision him being dealt. I don’t think that’s the message this front office wants to send now as they approach the next step of competing. He has a better chance of re-signing with the Pirates or getting an extension done with them prior to free agency this winter, or he retires. 

Carlos Santana:

There is still some value to Santana. He offers a little bit with that bat with some pop still and spurts of brilliance at the plate. What he does bring is plus defense at a tough position that is 1st base. He can also DH of course. He was brought in to platoon but has become a guy who has held his own as an everyday player when asked to be. Not that they’d get a ton for Santana but he’s a guy you certainly listen on and really possibly deal away. They could keep him for the culture he’s helped install and 1st base has been a barren wasteland for the Pirates that he’s at least provided a decent stopgap for so there’s internal value to that which could exceed the possible return in a trade.

Ji-Man Choi:

Sticking with the 1B/DH theme, Choi was brought in to platoon with Santana, maybe even take most of the starts as the lefty bat. He got injured early on and just came back. He will have a little bit of time to prove his value to a contender prior to the deadline. I think he has a likelier chance of being dealt than Santana if I had an uneducated guess on the subject. He isn’t as ingrained as Santana with the culture aspect and he might provide more value in just what he does for a contender possibly off the bench or as a DH type. 

Rich Hill:

Hill is an interesting one as he’s had an up and down season. It hasn’t been great for him lately. Regardless he is a veteran lefty backend rotation starter and that does become valuable to contenders this time of year. This could be the third straight year they flip the lefty starter they signed in the offseason (probably was the point of signing all of them anyways). Hill might be a little rich for what he is though as he signed an $8M contract. The Pirates might have to eat some or all of his remaining salary to facilitate a trade and maximize the return. I think that shouldn’t be an issue, at least we hope. 

Connor Joe:

Could Joe’s second stint with the team be cut so short? Possibly. Joe likely isn’t a starting level guy in many places (including the Pirates), he has some value as a bench bat and occasional starter. He can hit lefties well and that has some value. I ultimately do not think he’ll get traded because he still has so much contract left. He’s not a free agent until 2028 and the Pirates are still in position where they could use him considering some of their depth issues at the plate. He’s maybe a more valuable piece on this team than he would be on a contender right now. I don’t rule out trading him though. 

Mitch Keller:

This one has almost no chance of happening but the Pirates will definitely get calls. Keller has emerged as a very good MLB pitcher capable of anchoring a rotation. He isn’t a true ace but not many are. There’d be teams lining up to acquire Keller if he were truly available. A very good, controllable arm like him that can slot in as a number 2 or high-end number 3 on a contender would bring high value back to the Pirates in this market that is going to he starving for pitching like this. The Pirates need Keller just the same though. He is a foundational piece to this rotation that is about to be infused with young pitching where he will suddenly be the veteran mentor and his experience and journey as a big leaguer will be really valuable to them. Plus he obviously can provide on the field in a big way too if this season is any indication.

David Bednar:

I say it every year. An elite reliever on a bad team is simply a luxury but to a contender, it’s a necessary given how stretch runs and postseason baseball work. Every team needs it. Bednar would be perhaps the most valuable reliever on the market if he were available and with the Pirates likely not contending again, maybe he would be. Most likely not though. The Pirates haven’t traded him yet with chances the last two years to after the broke out as one of the best relievers in the league. If they haven’t yet, they won’t now. Not with their sights clearly set on contending in 2024 and beyond. If that is their plan, he will be a vital piece to the bullpen to build around instead of trading him away and possibly struggling ti replace him in a year they hope to compete. He will become more valuable to them than he’s worth in a trade if he’s pitching in games for them in a contending year. 

However, I feel like trading a reliever for multiple potential pieces that can help in other valuable areas is something to always be considered. While I do not see a team meeting the Pirates threshold to make the trade happen, what if one does? What if a team gives up a higher-end prospect that’s close to MLB-ready at an area the Pirates are lacking? I think that’s what it would take. Would the Pirates move him? Maybe given the positional value. The Pirates have always seemed to have a quality closer. It just happens. Maybe that’s just what this organization excels at finding. 

The issue is that the bullpen they have built right now leaves a lot to be desired and Bednar is a saving grace of it. To trade him would mean leaving a major hole in probably their weakest area. They’d have to really get a ton for him and have a quality plan to fix the bullpen once and for all this upcoming winter, which they need anyways but would need even more help there without Bednar. 

One other question is whether the Pirates would shop for a controllable asset at the deadline regardless of position in the standings. Maybe they want to do some offseason shopping early for a player with control and also with the upside of help now too if they even stay on the fringes of contention. It’s possible but I don’t see it as likely. 

The reason is that it looks like an extreme seller’s market is developing. Paying the prices it’d take to get any controllable asset is going to be tough to justify at this rate. The prices usually drop in the winter when the market is more saturated with options and the ‘trade deadline tax’ no longer applies. The issue is some available players now may not be available in the winter if they get traded now. If the Pirates identify a certain player they want now and feel it’s now or never to get that player, they could make that move. I don’t see it though. 

If the Pirates somehow make a run to become buyers, this conversation will change. For now, the expectation would be that they sell some of their short-term assets but the long-term guys stay put. I’d imagine that is how it’ll play out by the August 1 deadline. 

The top 10 most important players in the Pirates organization right now

Every team that wants to be successful in the MLB, or any sport, needs star players and just really good players throughout the roster. The Pirates have clearly lacked this over the years. Now, however, they have some guys who are really intriguing with chances to be that, some in the majors already but more to come out of the minor leagues. 

With that, I have compiled 10 players who are currently in the Pirates system, major and minor leaguers, that I feel are the most important pieces to this team’s success going forward.

Bryan Reynolds:

Going into the season, Reynolds was seen as their best player and be earned an extension due to that. He hasn’t been as good this season so far but he is no doubt one of the most important pieces to this organization going forward. He isn’t going anywhere any time soon. 

Ke’Bryan Hayes:

Another player on a long-term extension that isn’t going anywhere soon. His defense is awesome but his offense is inconsistent and now there’s talk his back issues could perhaps be chronic in nature. He’s one of their cornerstone players though and he’s vitally important to this operation.

Oneil Cruz:

Nobody is denying that he has star power. It’s unfortunate that he got hurt so early this season and in his career overall. He has a real chance to be this team’s best player and a perennial all-star. He is supposed to be this team’s franchise shortstop for a long time.

Mitch Keller:

Keller has become a vital part of this organization slowly but surely. He was just in the all-star game and deservedly so. He’s become a very quality pitcher and one that deserves an extension so he can be a very good and very steady part of this rotation for years to come.

Andrew McCutchen:

McCutchen should retire a Pirate, whenever that is. I think he has more seasons in him after his one-year deal expires this winter. He should be back as long as he wants to play. There’s always a place for him since he’s still a really good player. I think his presence is perfect for this young team and what he means for this organization, the fans and the city as well cannot he ignored. 

Henry Davis:

The 2021 1st overall pick has had a few weeks now in the big leagues and it looks like he can hold his own. He’s going to need to become a catcher too soon but the position versatility is fine to have given they’ll also have Endy Rodriguez soon. It’s as simple as they drafted him 1st overall. They need that guy to be successful in a big way considering the investment.

Endy Rodriguez:

Speaking of Endy Rodriguez, he is their other top catching prospect that should be up very soon. He also brings positional versatility that may be utilized too much early in his big league career but he and Davis have to eventually settle in as a catching tandem with versatility to do other things when the other one is catching. That’s the ideal. The Pirates haven’t solved their catching situation in a big way under Cherington except for one random good season from Stallings but then they traded him after (in hindsight a good decision). It’s time to solve that issue for a long time.

Quinn Priester/Jared Jones:

Both of these guys are in AAA. Priester will be up very soon while Jones looks more like a next year callup. At least one of these guys working out can give the Pirates a gigantic boost to their team. It’s hard to find quality pitching and buying it on the market takes a lot unless you get lucky. Having it built within the organization is a key to success consistently. The best teams have that going for them. 

Anthony Solometo:

Drafted by the Pirates in 2021 as a high school arm, it is impressive that Solometo is already in AA with a real chance to make it up to the big leagues next season. He’s going up the system fast and he’s rising fast as a prospect too, in the top 100 on some lists. He’s important in a lot of ways due to the pitching thing I mentioned with Priester and Jones but also that he is a lefty. The Pirates don’t have many of those in the system set to make an impact. A high-end lefty in the rotation is what this team needs. Solometo has potential for that.

Paul Skenes:

Just drafted number 1 overall by the Pirates, Skenes figures to have a fast track to the majors. The smart money would be on next year by June for his debut in Pittsburgh but he could push for earlier for sure. Davis is important as a top overall pick too but Skenes is even more important as one as he’s seen as a generational talent with ace written all over him. The other pitchers I mentioned might work out but they may still be missing something if Skenes doesn’t. Maybe it’s crazy hyperbole at this stage but this guy has a chance to be the best pitcher the Pirates have ever had. The expectations are lofty and he has to hit them for this thing to work. 

The one you will notice left out is David Bednar. I really like him and he’s one of their best players right now. He maybe should be on the list too due to his impact on the field and culturally as a Pittsburgh native. He just missed the cut for me here due to the fact that he’s a reliever and the reality is that due to that, his value of importance is slightly less everyday position players and starting pitchers. That isn’t to say he isn’t a vital piece too though. 

The Pirates have slowly built a foundation that has a lot to be excited for and it looks like it could all be coming together sooner rather than later finally. To me, these players listed are the 10 (or 11) most important players the organization has right now for the immediate future of this club.

The Pirates pitching plan is coming together

The Pirates used the 1st pick in the 2023 MLB draft on right-handed pitcher Paul Skenes. The LSU product is seen as a generational pitching prospect and the best since Stephen Strasburg in 2009. 

For the Pirates, they get the kind of prospect they’ve long needed in the system. They’ve had some really good prospects but none have been seen in the light that Skenes is in. He is going to be viewed as one of the best prospects in the game and very well could be the top pitching prospect in the game immediately. 

With this, the plan for the future of the pitching staff has come into focus. Skenes fits the timeline in which it seems a lot of the top pitchers in the Pirates system currently are projected to come up to the big leagues. 

Quinn Priester, the Pirates 1st round pick in 2019, should be up very soon. Jared Jones, who is already in AAA at age 21, has an outside chance at a September audition but will be a factor next season. Kyle Nicolas could see MLB action later this season too. Anthony Solometo, who is 20 in AA and drafted just two years ago, could be in a similar situation next year, if not up even earlier. Mike Burrows and Thomas Harrington look to be factors after that. Jun-Seok Shim, Bubba Chandler, Hunter Barco, Michael Kennedy and others will be guys in the next wave after that. This is of course all headlined by Paul Skenes, who should be able to force the issue and be up with the big club by next June or sooner. It also will include a number of other collegiate pitchers the Pirates took in the 2023 MLB draft. So there’s a lot of pitching coming the next three years. 

These guys will join a rotation currently lead by Mitch Keller, who has gotten better and better each year and is looking like a solid top-of-the-rotation guy that would be an awesome number 2 pitcher behind Skenes if he hits his ceiling and fast as he’s expected to. That would be a great 1-2 punch the Pirates haven’t had since Cole and Burnett in 2015. 

Besides Keller they have a lot of question marks in the MLB rotation currently. Rich Hill is not a long-term solution obviously. Oviedo and Bido don’t have the looks of long-term MLB starters. Roansy Contreras has lost something and the hope is he finds it since he looked like a rotation mainstay for the future at one point. If he regains form he can reclaim that. Luis Ortiz needs to figure some things out too to be an option. The clock is ticking on all of these guys besides Keller right now. 

The other guy is JT Brubaker, who they lost for the season. He showed to be at least a stable and perfectly fine major league starting pitcher, which is valuable in its own right. The Pirates hope he comes back and is at least that upon return. If he is, that’s a spot you can pencil in until/unless something better comes along. Vince Velasquez is also out for the season and they liked him before the injury and he was pitching pretty well. Maybe they’d want to bring him back on a new deal this winter and try again. I’d be for that. 

There is a good chance the Pirates go shopping this winter for another starting pitcher or two. They will need the help, even if they view the midseason reinforcements from the system as really good. You can never have enough good pitching. 

All in all, the Pirates clear strategy was to get these waves of pitching help in 2023, 2024 and 2025, maybe even some in 2026. They built up the system’s depth in that area for this window they are about to get in the middle of. Drafting Skenes again proves that and they added a true top-flight rotation kind of starter to their multitude of options to take it over the top. The strategy Cherington has had is coming together and it’s sooner than we think.