If I were ever to become President of the World, I would enact a rule that Christmas decorations couldn’t be put up until the Pittsburgh Pirates signed their first Major League free agent.
Granted, there would be backlash from those who are religious and who don’t care about baseball or the Pirates.
Most years under this law, you’re not putting those decorations up until the middle of December, and that’s after weeks of wading through the dark winter nights wondering if there will ever be any decorations at all.
The religious would no doubt disobey the rule, citing God’s law over man’s. They’re probably Dodgers fans.
Yet, this wouldn’t be as big of a problem for Pirates fans, who are a larger percentage atheist than any other fanbase in Major League Baseball, according to a stat I just made up that makes a lot of sense when you think about it.
You have to be comfortable with the idea that there is no God and we are all alone in this cold, dark existence, whenever your hopes for an entertaining relief from this world reside with the Pittsburgh Pirates.
And thus, my law would perfectly illustrate how it feels to be a fan of the Pittsburgh Pirates every winter.
Hopeless.
*****
Another way to experience the culture is to watch a video of someone trying to survive in the Alaskan wilderness by creating a bushcraft.
You start the video thinking “There’s no way this guy doesn’t die. They found this footage. This is found footage of a human being who died.”
After ten minutes of watching this guy just struggling through the cold, trying to achieve the basics that cavemen millions of years ago accomplished, and which humanity has long moved on from, you wonder “Who would ever do this to themselves? Who would live this way when modern conveniences are available for a cost?”
But as you see him surviving more and more, you start to root for him, and his methods.
Hell yeah! Bonfire the shit out of that wet ground to create a dry area suitable for sleeping!
If it’s still wet, burn baby burn.
You know what? Those baked beans do look amazing.
Sure, everywhere else in the world, these beans would be a side, but they are the main feature for this person’s winter feast.
And occasionally, he’ll roast a lamb shank, and you know it is serious in that episode.
Watching the Pirates during the winter is like facing the brisk reality that you’ll be wandering in the snow for a long time, trying to find dry land, burning through Twitter arguments about fringe-average free agents like they’re wilderness brush, and eventually talking yourself into a can of beans potentially being the most amazing meal a human being could consume.
It’s sometimes about finding hope where none exists.
*****
I could keep going with the analogies of what it’s like to follow the Pittsburgh Pirates in the winter, but let’s just stick with reality.
In five offseasons as General Manager of the Pittsburgh Pirates, Ben Cherington has cooked nothing but beans.
A first base rental. A veteran lefty for the rotation. A late inning reliever. Defense up the middle.
These are the moves he makes each offseason. These are all complementary pieces for a contending team, and only two teams have lost more games than the Pirates from 2020-2024, with Cherington as the GM.
These are not moves that will turn the Pirates to contenders, nor assist their players from within toward contending.
This tanking has led to some long-term hope, most notably with generational pitcher Paul Skenes. The Rookie of the Year favorite will be the litmus test of whether the Pirates are a serious organization over the remainder of this decade. If Skenes continues pitching like he did in his rookie season, then he will set franchise records for highest salary around the 2027-2028 seasons.
We don’t have to wait to see if they pay Skenes to determine whether the Pirates have any semblance of being a serious Major League organization.
It is beyond time for this team to stop tanking and start trying to contend. That begins in the offseason.
I am someone who proclaimed in the past that “the way” in baseball for small market organizations was to tank for a few years, only to flip the switch and become a competitive force. I now see why that switch is so difficult to flip.
Losing becomes a habit.
At Some Point the Players Need to Commit the Effort, But…
Bryan Reynolds had an MVP-candidate season in 2021, but didn’t replicate that performance the following years. The amount of daily effort needed to perform at the level Reynolds showed is no doubt personally debilitating to the player. Not just in the short-term, but the long-term. Why would Reynolds put that effort forth in 2022 or 2023, when no help was added to this team?
Reynolds did put forth the effort in 2024. This team received a spark when Skenes arrived. It started in the rotation, and when Reynolds started hitting during the summer, the Pirates began looking like contenders.
It can’t just be on Reynolds, Oneil Cruz, and the starters in the rotation who make them contenders.
The Pirates need more people to share the workload, rather than relying on one or two people to sacrifice themselves for a six-WAR season.
There are some internal candidates who can help the Pirates in 2025 — like pulling out a bag of beans inside the bushcraft and baking them while focusing on all of the spices that will elevate the feast.
The biggest question I have for this offseason is whether Ben Cherington will finally bust out a lamb shank, in the form of an external addition that reflects this organization is ready to contend.
Because until Cherington shows he is serious about pushing the chips in on a specific year, why would any player on the roster sacrifice themselves for six months?
When It’s Always About Putting the Team First
Why would the group sacrifice themselves and give extra to this team? We are coming off a year where the Pirates didn’t give $450,000 in performance bonuses to two players who they marketed in a way to hide their inactivity toward building a real contender.
Tellez shouldn’t have been their priority signing at first base last season. That should have been Carlos Santana, who wanted to return, but who the Pirates passed on to save $2.5 million dollars over Tellez. Santana was the fourth most valuable first baseman in the game in 2025, and has always been a better option than Tellez.
The Pirates opted for a few million in savings, over a better option who actually performed for them and wanted to be with them. Then, they sold Tellez as a team player and an overall good guy.
I watched Rowdy Tellez eat a steak on a stone in an awkward interview with Hannah Mears that pushed him as a guy you’ll love to root for all summer. This followed the blunder from Tellez when he told Pirates fans (who were fed up with the organization’s cheap ways) when they should or shouldn’t boo.
Tellez went away from the team to re-learn how to hit mid-season. He returned and helped Reynolds and Cruz with the mid-season contending push. There were calls from team-friendly accounts online for all haters to rescind past criticism of Rowdy.
When he fell off in September, you could forgive him for not putting forth the best effort in a year where the team waited until after the season to make a change with their obviously flawed hitting coach. Tellez never quit, and was a big reason the Pirates were interesting for a few months. He actually ended up being the guy they marketed, even if he probably cared too much about outside perception to be effective in baseball.
And the Pirates released him with a week to go, over $200,000 in performance bonuses.
The Pirates weren’t serious last offseason. They just focused on saving money, and grabbing the cheapest option for survival.
They repeated this at the trade deadline. With the prospect capital to land a Jazz Chisholm or a Randy Arozarena for several seasons, they instead turned to a plan that brought in closer to replacement level Isiah Kiner-Falefa and Bryan De La Cruz, while also somehow cutting payroll in 2024.
Then, after naming Kiner-Falefa the starter at shortstop and increasing his role with the team, they held him out of the lineup during the final game of the season, which prevented him from reaching $250,000 in performance bonuses. He may have reached those, had he remained with Toronto.
This organization not only avoids spending money on external additions, but they pinch every penny from those who help them from within.
The penny-pinching never leads to a vacation from the constant losing.
Will the Pirates Be Serious?
Like Charlie Brown wondering if Lucy will pull the football away, the thought runs through your head: “Are they just waiting until the offseason to make the big addition?”
That annual thought gives way to “Maybe they will make a splash at the deadline.”
The deadline arrives, and it’s always the same money-saving, value-seeking approach.
And the cycle continues.
Will this be the offseason that Cherington breaks the cycle?
By comparison, it took former General Manager Neal Huntington five years until he made a significant offseason splash. I’d expect any change in approach from Cherington would happen just as suddenly and as unexpectedly as when the Pirates added Russell Martin and Francisco Liriano over a decade ago.
This would be the year for Cherington to break the cycle and add to the team.
It’s time to stop asking the internal players to build the winning structure themselves, and bring in some survival assistance from the outside.
MLB Trade Rumors released their top 50 free agents, with predictions. The Pirates were predicted to go after outfielders and relievers. To get a better idea of their offseason needs, I’ve broken down each position below with my own outlook for the offseason and the team needs.
Catcher
League Rank: 19th (2.3 fWAR)
2025 Internal Options: Joey Bart, Henry Davis, Endy Rodriguez
Early 2025 Preview: The Pirates have a promising internal trio. Former second-overall pick Joey Bart had a breakout season in 2024, after being acquired from the Giants. Former first-overall pick Henry Davis has shown power in Triple-A, and improved defense behind the plate. He still needs to make the successful jump to the Majors. Endy Rodriguez has the best defense of the trio, but is returning from Tommy John and has also yet to hit in the Majors. There are a lot of questions with this group, but there’s a lot of upside here for the Pirates to have an above-average catching group in 2025.
Offseason Outlook: I would actually be surprised if the Pirates bring in a Yasmani Grandal or Austin Hedges type this year. I think it’s likely they add a veteran for Triple-A, but they have a great situation there with Jason Delay as a defensive depth option. Grant Koch was used as an emergency option in 2024. Carter Bins, Abrahan Gutierrez, and Dylan Shockley all provide depth for the upper levels. I think the offseason here will be about increasing depth.
First Base
League Rank: 25th (-0.5 WAR)
2025 Internal Options: Billy Cook, Connor Joe, Jared Triolo
Early 2025 Preview: The Pirates are in the same situation they’ve been in since trading away Josh Bell on Christmas Eve 2020. They’re entering the offseason with their first base position entrusted either to a veteran rental via free agency (Rowdy Tellez 2024, Carlos Santana 2023, Dan Vogelbach 2022) or a post-prospect, aka a former top prospect who still might have a shot to make it in the Majors beyond the age of 25 (Colin Moran 2021). In this case, their internal options trend toward the post-prospect hopes. Billy Cook was acquired in a minor deal at the 2025 deadline, and has shown power the last two seasons in the upper-levels. He’ll be entering his age-26 season, and can also play in the outfield. He’s the most exciting option of the internal candidates, but profiles as an average starter at best. The best move might be moving someone else to first base, which I’ll get to when discussing Bryan Reynolds.
Offseason Outlook: A veteran like Paul Goldschmidt would cost around $15 million for one year, with the hope that he performs better than the .716 OPS in 2024. That amount would blow through most of the likely low offseason budget the Pirates have, without adding any more certainty to the team. It might be best for them to continue the value approach they’ve had the last two years, with a catch. They don’t need the value player they sign to be an everyday starter, due to the presence of Cook and the catchers. Former Pirates Bell, Santana, and Tellez are available. They could also spin the wheel and go with someone new. I think the most impactful move they could make here is moving Reynolds to first base, and focusing their offseason additions on the outfield.
Second Base
League Rank: 24th (1.0 WAR)
2025 Internal Options: Nick Gonzales, Liover Peguero, Jared Triolo, Nick Yorke
Early 2025 Preview: The Pirates entered the 2024 season with a competition between Nick Gonzales, Jared Triolo, and Liover Peguero for the starting second base job. It’s been like watching a marathon race with a few lead changes, but no one pulling away. Gonzales is the current front-runner. He put in a lot of dedication toward improving his hitting last offseason, and got a year in the Majors where he put up just slightly below-average offense, with above-average defense. If Gonzales doesn’t hit consistently, the Pirates acquired Nick Yorke at the deadline, giving them another option. Both Gonzales and Yorke were taken in the first round of the 2020 draft.
Offseason Outlook: With so many internal options, I doubt the Pirates will focus on second base. I could see them adding a veteran middle infielder for the bench, but that would be with more of a focus on the shortstop position. The 2025 season should be about seeing whether Gonzales can close it out and win the job. Yorke and Peguero would be the top alternatives, if they can reach their upsides.
Shortstop
League Rank: 21st (2.5 WAR)
2025 Internal Options: Isiah Kiner-Falefa, Alika Williams, Nick Gonzales, Jared Triolo, Liover Peguero
Early 2025 Preview: The Pirates made the decision to move Oneil Cruz to center field late in the 2024 season. Cruz was one of the worst defensive shortstops in the Majors, and has shown better defensive abilities in center. A few weeks before moving Cruz, they acquired Isiah Kiner-Falefa in a deadline deal. A few weeks before that, they were testing Jared Triolo at the position. Kiner-Falefa brings better defense than Cruz or Triolo, but historic below-average offense. That makes him better than Triolo internally. IKF is under contract in 2025 for $7.5 million. The Pirates have a defensive backup in Alika Williams, but they don’t have an internal standout for the long-term job. Liover Peguero would be the best long-term candidate. He hit for a .794 OPS over the final two months of the 2024 season, was called up to the Majors for the final three games, and is currently hitting well in the Dominican.
Offseason Outlook: The question is whether the Pirates commit to Kiner-Falefa in 2025, or turn to the outside. The best realistic free agent option looks to be Ha-Seong Kim, who will begin the season on the injured list, returning from a shoulder injury. He is projected to cost about $5 million more than Kiner-Falefa, but would provide the best chance of an upgrade. In either case, the Pirates are looking at a one-year option who is defensive-minded, with the hope that Peguero takes over in the long-term. I think the addition of Kiner-Falefa at the deadline was more about getting a head start on building the 2025 team. The writing was on the wall with the progression away from Cruz at short, and they traded their breakout prospect of the year to get Kiner-Falefa. I don’t expect anything at this position over the offseason, outside of defensive depth.
Third Base
League Rank: 23rd (0.6 WAR)
2025 Internal Options: Ke’Bryan Hayes, Jared Triolo
Early 2025 Preview: How much a year can change. One year ago, Ke’Bryan Hayes was winning a Gold Glove award, while coming off a breakout season at the plate, and his second straight 3+ WAR season. This year he is coming off his worst MLB season, and dealing with a serious back injury that raises long-term questions. He still shows the defensive ability, but will need to find a way to hit like he did in 2023. Jared Triolo won a Gold Glove as a utility player this offseason. He hasn’t shown an ability to hit in the Majors either, but would provide defense if Hayes can’t play. The Pirates could also shuffle Kiner-Falefa to this position if needed, and if they have a shortstop option.
Offseason Outlook: There’s absolutely zero depth in the upper-levels of the minors at third base, unless the Pirates go a complete 180 and turn to an offense-led guy like Malcom Nunez. That would also require Nunez to start hitting enough to warrant a promotion. The best approach would be to roll the dice with Hayes and hope for the best health, while adding an alternate from the outside for depth behind Triolo. I could see them adding a veteran to the Triple-A squad for that depth.
Left Field
League Rank: 24th (-0.3 WAR)
2025 Internal Options: Bryan Reynolds
Early 2025 Preview: Bryan Reynolds had one of the best offensive seasons of his career, hitting .268/.328/.430 with a surge during the summer months that put the Pirates in contention. His defense in left field was among the worst in the game. The Pirates have him signed into his mid-30s, and at some point they will need to move Reynolds off the position before his defense becomes prohibitive. That some point may have already passed.
Offseason Outlook: If the Pirates move Reynolds, first base would make the most sense. This would also allow them to focus their offseason budget on a corner outfielder, where they might find more value adding a hitter. Worst case, they end up with another Reynolds, who ultimately provided above-average offense and the worst defense in the league. That profile in the outfield should be easier to replace and improve upon than a guy who could hit 30 homers at first base — which I believe Reynolds could do if he didn’t wear himself down in the outfield every night.
Center Field
League Rank: 27th (0.8 WAR)
2025 Internal Options: Oneil Cruz, Billy Cook
Early 2025 Preview: The Pirates made the most impactful move for their 2025 season when they moved Oneil Cruz to center field. It was a small sample, but Cruz showed promising defense at the position. What the Pirates need is for Cruz to hit at an above-average rate or better, without detracting from the defense. He has the hitting potential to be among the best in the game. Even if he doesn’t reach that level of consistency, he won’t be giving away as much value at the new position. An interesting alternative would be Billy Cook, who is a power/speed option that should be viewed as depth to Cruz.
Offseason Outlook: This position should belong to Cruz until he shows that he can’t handle it. The Pirates could look for a defensive outfielder to add depth to their system. Their outfield options in the upper levels are thin. The best option is Matt Gorski, a power/speed/defense option who hasn’t hit consistently enough to make it out of Triple-A. Beyond Gorski, a lot of the outfield depth is made up of converted infielders. I’d expect some depth to be added here.
Right Field
League Rank: 29th (-2.0 WAR)
2025 Internal Options: Bryan De La Cruz, Jack Suwinski
Early 2025 Preview: Last offseason, Jack Suwinski was coming off a 26 home run season with above-average overall hitting. That made him a clear choice for the starting role. He spent the 2024 season struggling to the point where he didn’t even look like he belonged in Triple-A. The Pirates acquired Bryan De La Cruz at the deadline, who has always been a league-average hitter with power. De La Cruz slumped immediately after joining the team. They’ll turn to these two in hopes that one can figure it out in 2025.
Offseason Outlook: If the Pirates move Reynolds to first base, then they would absolutely need to add an outfielder this offseason. Even without that move, it would benefit them to add someone so that they aren’t relying fully on De La Cruz and Suwinski. Both look like depth options for a contending team. If the Pirates want to be contenders in 2025, it will happen by adding some reliability to their offense. This would be one of the best places to upgrade, replacing two of the worst performers in the game in 2024.
Designated Hitter
League Rank: 11th (1.4 WAR)
2025 Internal Options: Andrew McCutchen
Early 2025 Preview: This position sums up the entire Pittsburgh Pirates rebuild under Cherington. Designated Hitter is by far the best performing position the Pirates had in 2024, and that’s due to Andrew McCutchen. He’s been one of the few consistently above-average performers over the last two seasons. McCutchen was brought back on the insistence of Pirates owner Bob Nutting. Meanwhile, Cherington’s rebuild looks to be focused around using first base and the designated hitter position for their rotation of excess catching options. The dilemma presented is that in order for that promising trio to work out, they need to detract playing time at DH from McCutchen, who is an icon and one of their best performers.
Offseason Outlook: Nutting has vowed that McCutchen will be a Pirate as long as he wants to play in the Majors. That puts Cherington in a situation where he has a guaranteed guy on the roster who he has to work around, after investing so many resources in the early rebuilding days toward catchers who could split in the DH role. The current catching situation is the most promising aspect of the rebuild, with hopes that Davis and/or Rodriguez can figure things out in the Majors and be long-term options. In the short-term, McCutchen is one of their best hitters, though it might be beneficial for him to start taking a step back for the younger guys. This will be an interesting situation, because Cherington doesn’t have great job security right now, and the best thing that could happen for him is a breakout from multiple catchers. That becomes more difficult to envision with McCutchen as a regular starter at the DH spot, though McCutchen makes obvious sense for that position — both in terms of performance and for his connection to the city of Pittsburgh. Really, this all just speaks to the performance of the rebuild. Five years later, the offense is filled with bottom-third performances, one of the best hitters was imposed upon Cherington, and that hitter is blocking the few long-term hitting options from his rebuild. McCutchen would be a gift for any real contending team.
Starting Rotation
League Rank: 15th (11.4 WAR)
2025 Internal Options: Paul Skenes, Mitch Keller, Jared Jones, Luis Ortiz, Bailey Falter, Johan Oviedo, Bubba Chandler, Thomas Harrington
Early 2025 Preview: This area was the most promising aspect of the team in 2024. It only looks to get better, with top prospects Bubba Chandler and Thomas Harrington on the verge of the Majors. The boost that Paul Skenes and Jared Jones provided this year could be replicated with Chandler and Harrington. The Pirates extended Mitch Keller, then watched him turn into one of the more reliable starters in the game, especially after Skenes arrived. They have a trio of interesting young options to round out the rotation in Luis Ortiz, Bailey Falter, and Johan Oviedo. All three have pitched well enough to earn a rotation spot.
Offseason Outlook: Depth. Depth, depth, depth, depth, depth. More depth. If you were to go to a liquor store and find a cabinet that held the rare items, you might ask the clerk to find you a Master’s Collection by Woodford Reserve; and as you take that whiskey home and drink a glass by the winter fire, marveling at the plethora of aromas, scents, and flavors, you’ll be reminded that Jake Woodford made five starts for the 2024 Pittsburgh Pirates, and you’ll think to yourself a single word near the crackling of the cedarwood: “Depth.” And with a nod, you will take a sip and understand that the Pirates probably should add a veteran starter this offseason, even if it’s not the most exciting name. They have the exciting names. They have more internal depth than ever. But you can never have too much depth. They also don’t have any pitchers with experience pitching in serious games beyond early-August. I could see a veteran brought in, which would make the fifth starter battle between Ortiz, Falter, and Oviedo one worthy of a contending rotation. This paragraph was written by my hope for someone from Woodford Reserve to contact me with a free thrice-barreled bottle to get me through this Pirates offseason. You guys have three days from reading this until I re-write this paragraph to feature Old Forester. Make your move.
Bullpen
League Rank: 18th (3.4 WAR)
2025 Internal Options: David Bednar, Colin Holderman, Kyle Nicolas, Carmen Mlodzinski, Dennis Santana, Dauri Moreta, Braxton Ashcraft
Early 2025 Preview: The bullpen was a strength until the 2024 season. David Bednar entered the season as one of the best closers in the game, and finished the season with the Pirates turning to Aroldis Chapman. The Pirates have some interesting options for the late innings, with my long-term preference being Dauri Moreta, Kyle Nicolas, and Colin Holderman in that order. Carmen Mlodzinski and Dennis Santana both have provided good middle relief options at times. Braxton Ashcraft, a starter in Triple-A, is an interesting option if he moves to the bullpen. Fueled by a fastball/slider combo, Ashcraft has dealt with injuries as a starter, but could be a late inning reliever.
Offseason Outlook: The biggest move the Pirates have made under Cherington has been the one-year, $10.5 million deal given to Aroldis Chapman. They could repeat that in 2025, either bringing back Chapman or turning to another option. Tim Dierkes of MLBTR predicted David Robertson to the Pirates, which would be along the same lines as Chapman. The Pirates would be exploiting a market inefficiency, where obviously good relievers are only available to big market teams because it’s just not smart for a small market team to spend so much on this position. Chapman showed that to be false in 2024, providing one of the most consistent presences all season. If the Pirates added Chapman or Robinson as their closer, they could use Bednar as a setup man and bank on a comeback. This would put less emphasis on Moreta, Nicolas, or Holderman to be eighth inning options. It would also help to solidify the entire pitching staff as the strength of this team that otherwise features promising defense and poor offense. I could see the Pirates addressing their bullpen once again this offseason in a big way. They also could use a lefty reliever, and could turn to departing free agents Ryan Borucki or Jalen Beeks to fill that need.
Pittsburgh Pirates 2024-25 Offseason Outlook
Priority Needs: Starting 1B, Starting Corner OF, Veteran SP, Closer, Lefty RP
Depth Needs: Defensive Middle Infielder, Defensive Center Fielder, Minor League Catching Depth, Triple-A rotation veteran, Plenty of Bullpen depth
Offseason Outlook: There’s really only two ways this offseason will go.
Option A is that we see another year of the same from Cherington — a few low-cost rentals in a passive approach to upgrading the team, while hoping that the existing options take the necessary step forward to push the team toward contending.
Aka, he will just fill the positions with warm bodies, and we’ll be sold on the hope of improvements from the players they already had on their roster. The latter might happen from the addition of a hitting coach, but this team needs outside help.
Option B is that Cherington makes his first significant signing to push this team toward contending status. The Chapman signing last year was the only move that could be defined as such, but adding an elite reliever and nothing else isn’t really trying. Serious moves to add a legitimate upgrade, and fewer Marco Gonzales/Rowdy Tellez value bin shopping in December would indicate the Pirates are serious about being contenders.
Their trade deadline approach seemed to be fueled toward adding help in 2025. For that reason, guys like Isiah Kiner-Falefa, Bryan De La Cruz, Nick Yorke, and Billy Cook should be considered as part of their plan in 2025. Even with those guys, the Pirates still have a lot of needs to address in order to climb above .500 and contend next year.
Will this be the year the Pirates provide hope in the offseason by trying to contend?
Or, will it be another long, slow, cold, dark, depressing drive to an inevitable 75?
