The Pittsburgh Pirates enter their off-day on Thursday with a 36-38 record. They’re third in the NL Central, which is currently dominated by the Milwaukee Brewers at 44-30, with four other teams below .500. The Wild Card race is led by two teams who are under .500, so the Pirates are only half a game back.
There are currently nine teams in the National League with a winning percentage between .473 and .493. Eventually, two of those teams will go to the playoffs. Getting there is as simple as winning more games than you lose. That hasn’t been simple for any of these teams, including the Pirates.
The Pirates have a chance to show whether they’re serious about contending. Years ago, I had 2024 circled on my calendar as the deadline for when the Pirates should be expected to start contending on a tear-down and rebuild plan with Ben Cherington as the General Manager.
The current team doesn’t scream contender, but only four National League teams do this year. Eventually, the Pirates need to become one of the true contenders, and not a team trying to sneak in to the Wild Card spots.
For now, they have a chance to reach the Wild Card round this year, and they definitely should be focused on the post-season in their plans for 2025.
The next eight months are going to reveal how serious the Pirates are about winning, as this rebuild turns to hopeful MLB success.
To get an idea of what to expect from this team, I’m looking at the responsibilities over the next eight months — and then some — from the owner all the way down to the players.
The Owner: Bob Nutting
This rebuilding process hasn’t been a strain on Bob Nutting. According to the inimitable Ethan Hullihen’s payroll tracking, the Pirates spent a reported $267,681,830 from 2012-2014. They spent $233,649,024 between 2021-2023. That’s less than they were spending a decade ago.
I don’t know if you’ve shopped for anything in general lately, but the prices of everything these days is way above what it was in 2012-2014. That includes MLB payrolls. The Pirates were contending in those earlier years. They were tanking in 2021-2023, so they held one of the lowest payrolls in the game. This tanking led to them being in position to draft Paul Skenes, who received the biggest bonus in MLB draft history.
The winds of the rebuild are starting to shift on the north shores, from a financial standpoint.
According to Hullihan, the Pirates are on pace to spent $121,502,861 in Competitive Balance Tax payroll this year. That would be their highest payroll in franchise history, eclipsing the $116,055,536 in 2015.
Perhaps that’s a sign of the MLB payroll inflation. A modern day tank and rebuild costs in the range of that 2012-14 contending buildup a decade ago. A modern day buildup to contending team like the 2024 Pittsburgh Pirates starts where the 2015 Pirates — the pinnacle of Bob Nutting’s comfort in spending, according to the fantastic reporting by Stephen Nesbitt — capped the organizational payroll.
Nutting is now getting to the point where the Pirates will start costing franchise records in payroll every single year. His history of spending has to make you wonder if he’s comfortable with the risks.
Let’s say that the correct call in the offseason of 2015 was to commit to three more years of payroll increases. The 2015 Pirates just finished with the second best record in the game, and were still among the lowest spenders in the league. They followed with decreases in spending each year in 2016, 2017, and 2018. In total, they spent $322,970,016 in those seasons. If they had increased payroll just $10 million per year over the 2015 team — $125, $135, and $145 million in 2016-18 — they would have spent $405 million in those years. That’s a difference of over $80 million.
The difference is how much Bob Nutting wants to win.
He had three years of one of the best MLB teams, which had the unfortunate fate of hosting three wild card games and only one extended playoff run. Two of the wild card games featured the Pirates going up against the best pitchers in the game. The Pirates needed to add to these teams in order to get beyond the wild card crapshoot.
Nutting instead scaled back spending, to the point that he took capital upgrades out of team payroll. He settled for a reduced chance of winning, rather than pushing forward to truly contend.
Imagine what that 2016 team might have been with an extra $16 million. Maybe they don’t have to trade Neil Walker to solve their pitching problem with the similarly priced Jon Niese?
Imagine the 2017 team with an extra $25-26 million. There was a lot of focus on Andrew McCutchen and Gerrit Cole leading the team following the 2015 season, but who did the Pirates spend to put around those generational talents?
Imagine the 2018 team with an extra $40 million. Maybe they don’t trade Cole and McCutchen, and give it one final run. Maybe they still trade for Chris Archer in that scenario, rather than trading for him in the same year they traded Cole and McCutchen away.
When Nutting sets such a low competitive payroll ceiling, it forces inexplicable decisions.
The Pirates have invested in this upcoming window of contention already. Or, they’ve made commitments to invest.
Bryan Reynolds was signed to an extension last year that will pay him through the 2030 season, with a 2031 option for $20 million. He’ll be making $15.25 million per year, starting in 2027, while getting paid $12.5 million next year.
Mitch Keller was signed to an extension this spring, and the extension accurately reflects that Keller is a true Major League starter. The Pirates will pay him $69.5 million over the next four seasons, which buys out his final year of control and his first three free agent years. Keller is under contract through the 2028 season.
The Pirates did some front-loading when they signed Ke’Bryan Hayes to an extension early in the rebuild. He’ll make $7-8 million per year from now through 2029, with a $12 million option in 2030.
Those three players alone will cost $34.25-43.25 million per year from 2025-2028. The Pirates have a total commitment in those years of $155.5 million to three players.
If the Pirates only spend what they spent from 2015-2018, they’d have $283.5 million for the remaining teams. That would point to payrolls in the $105-115 million range, and the Pirates are already above that amount in 2024, as they should be.
The question I’m getting toward is how much should Bob Nutting be spending in the payoff of this long rebuild?
I think an argument can be made for the $540 million range over the next four years. That’s the current $120 million as a starting point, with $10 million added per year in the build up process. It also gives the Pirates $100-125 million per year to build a team around their big three.
That money can go a long way with young, cheap talents on the roster like Jones, Skenes, and Gonzales.
I’ll give credit to Nutting for being more present around the Pirates than he had been in the past. He also gets credit for pushing for Andrew McCutchen to have a spot on the team until he retires.
The big test starts now, determining whether Nutting will spend on a winner, or if he’ll just spend enough to give a chance at winning.
The General Manager: Ben Cherington
I’ll start by saying that I think Cherington did a good job building the base of this team. We can debate how they got here. One unlucky lottery ball from the 2023 draft, or one less inherited addition from the previous front office and this Pirates team would look much different. Right now, they look like a team that can post a winning record, and maybe luck into the wild card round. That’s the floor of the 2024 expectation when Cherington was hired.
I was arguing for the Pirates to do a tear-down and full rebuild back in 2017-18, rather than their middling approach of trying to luck into the wild card game. I put that plan less on the old front office, as they were restricted by the payroll ceiling from Nutting.
Cherington has done the modern day approach of a linear teardown and rebuild process. If done correctly, this process might never have to be repeated in Pittsburgh. It’s too early to say whether the Pirates can grow from this point, so my grade of Cherington is positive, but incomplete.
What I like is that Cherington has invested in a core of players who will be in Pittsburgh over the next four seasons. Reynolds and Keller have shown themselves to be the most consistent hitter/pitcher on this team in the first half of the 2024 season, and both above-average in relation to the league. Hayes is having a down year, and has dealt with an injury. He did win his first Gold Glove last year, while showing promise with the bat. His defense alone makes his contract a value, and provides support for the strength of this team.
Paul Skenes and Jared Jones are the biggest additions from the farm system to the 2025-2028 window. The Pirates took Skenes first overall in 2023, in a decision that wasn’t a consensus slam dunk at the time. Credit to Cherington for not shying away from the fear of investing in an elite pitcher. As for Jones, he was drafted by a scouting department that Cherington left intact, which had a good history of identifying elite pitchers at a young age.
The Pirates struggled in the past with getting the type of results we’re seeing out of Jones and Skenes from their previous pitching phenoms. My belief is that the early results from Jones and Skenes represent a positive from the individualized development plan under new minor league director John Baker.
In the past, the Pirates may have held back their pitchers with too many pitches, or a specific universal approach to development. I covered the Tyler Glasnow changeup search in 2016-17, and today he’s one of the best pitchers in the game, without throwing a changeup. The Rays and Dodgers and other organizations realize what I hope the Pirates have opened themselves up to realizing: They should let elite pitchers throw their stuff with confidence until they show they don’t belong in the majors. Then, have those pitchers develop more pitches to keep them in the majors, or to get them to stick in the majors if they struggle.
Skenes showed this by quickly adding his splinker in pro ball, but also by incorporating his curveball more often as the league adjusts to his fastball. Jones has been working on his curveball and changeup, to eventually pair with the elite fastball/slider combo that has him in the big leagues.
I feel like the Pirates development of the past would have held Jones back until he could prove he could get MLB hitters out with four pitches. I also don’t know if they would have gotten to such a unique pitch as the split fingered sinker from Skenes, as there was possibly too much risk-aversion with pitchers in the previous group.
Keller has been the best development story. If you use fWAR as a baseline for player production, Keller reached a 1.1 WAR in 2021. He improved to 2.1 in 2022, 3.3 in 2023, and is on pace for that level or higher in 2024. He’s gone from a below-average starter to an above-average starter, adjusting his pitches and approach along the way.
The Pirates now have a big three of Mitch Keller, Paul Skenes, and Jared Jones through the 2028 season. That’s a credit to Cherington’s build that this rotation looks like it could contend in the playoffs for years.
Because pitchers get injured, they might not get 12 MLB seasons out of those three players. That would be around 2400 innings. If they get eight full MLB seasons from this group, in their elite form, over the next four years, that will be a positive result. Anything beyond about 1600 innings from this combined group in 2025-28 would be a serious win for the Pirates.
That’s the challenge that Cherington faces in building a division contender. He can’t just rely on three pitchers he’s added so far to stay healthy. Fortunately, he’s shown an ability to identify left-handed pitching talent at the MLB level. The strength of the Pirates’ system is also pitching, with many of their top prospects being pitchers in the upper levels. They’ve got some depth here for the future.
The weakness of the Pirates has been hitting. Their MLB approach is unclear, and questionable when it’s cleared up. Their minor league approach has very few players performing to their talent levels, and many being the exact opposite of the hitter they were described as when added to the system.
The same amateur scouting department that was strong on pitching was weak at identifying hitting at any level. The old development process was too aligned to old school methods. The Pirates have gone to extremes to incorporate data into the development process, but they’ve gone too far to the other extreme. They’ve eliminated a lot of classic coaches who are better equipped at getting inside the mind of a hitter during the teaching process. In my opinion, the Pirates have potentially paralyzed their hitters with too much analysis of which pitches to hit, without a core understanding of how to hit in the majors.
They need to find a middle-ground, where hitters are being taught the Andy Haines blackjack approach of hitting strategy that relies on the pitchers being a constant; but also a development approach that teaches each individual hitter how they can be a constant toward any pitcher.
The Pirates need hitting. The next eight months will cover the upcoming trade deadline, plus the complete offseason.
The Pirates can make a run at the post-season this year if they add a hitter to this team at the trade deadline.
They should be focused on the post-season in their offseason plans for the 2025 season, and will definitely need to add a hitter from the outside to make such a run.
The window is starting to open for Cherington. He’s got his core established, with a big three in the rotation, and only two players who can be relied upon in the field and at the plate. There needs to be at least one more hitter added to this mix. The earlier the Pirates add that impact bat, the earlier this window has a view of a playoff calibre team.
The Manager: Derek Shelton
I have given Derek Shelton a pass for most of his time in Pittsburgh. It can be difficult to manage to win at the Major League level when the focus of the team building isn’t yet on winning at the Major League level.
Shelton has had some questionable moves this year, but I do like how he’s managing the bullpen lately. I don’t think he’s doing the lineups any favors with the constant shuffling. That’s a chicken-and-the-egg question of whether the players need consistency to be consistent, or whether the team should reserve consistent spots only for the players who show themselves to be consistent.
This is the first season where the Pirates have had a team that could win and make the playoffs. It’s the first season where Shelton’s decisions have mattered. He had four years to prepare for this point.
My question is whether he can avoid prolonged slumps, and possibly drive the Pirates into a prolonged winning streak in the future?
We’ve seen the prolonged slumps over the last few years, and hopefully the Pirates have already exited their 2024 slump. The Pirates over the last month have been a .500 team, never winning too many in a row, but never losing too many in a row.
Which direction will Shelton navigate this team for the remainder of the season? How will his decisions set the team up to win in a consistent way?
Cherington will need to give Shelton the best roster to work with, and that includes coming through with reserves in roster shuffles when the team needs help. We just saw that process play out recently with the pitching in the top two levels getting a boost, and sending a lot of guys to the majors to help the injuries in the rotation.
This year, Cherington needs to provide depth to keep the team at their current .500 level, with the possibility to add a hitter who can take them to a playoff push. But it’s on Shelton to get the most out of the team he’s given. The next three months will reveal Shelton’s growth as a manager.
The Players
Ultimately, the players need to perform.
Reynolds enters this off-day with a 17-game hitting streak. The last time Keller went less than five innings was the first start of last season.
Skenes is performing, and Jones is starting to get the league adjusting against him. This year might be one of few times where Skenes, Jones, and Keller are all healthy and performing well. It would be a waste to not boost this group.
But where does the boost go?
I trust Hayes to get back on track at third base. Oneil Cruz at shortstop, Reynolds in the corner outfield, and Andrew McCutchen as the designated hitter are positions that should remain with trust for this season. Connor Joe bouncing between corner outfield and first base makes sense. Nick Gonzales should be given every opportunity to stick at second base. I’m interested to see what the Pirates get out of Joey Bart and Henry Davis the rest of the season behind the plate.
The areas of upgrade are the same areas the Pirates tried to upgrade on the cheap in the offseason. Rowdy Tellez is starting to hit this month, and the Pirates will be justified in keeping him around if he keeps hitting the rest of the year. Michael A. Taylor has some of the best outfield defense in baseball, but has shown some of the worst hitting of his MLB career. The corner outfield platoon of Jack Suwinski and Edward Olivares has been worth a combined -1.5 fWAR this year.
There are a little over five weeks remaining until the trade deadline. That provides enough time for those four players to hit with consistency. If they don’t hit with consistency, the Pirates would have a clear place to look for an upgrade at the deadline, with a few positions open to shore up before playoffs return to the North Shore.
The Next Eight Months
I think the Pirates have a chance to sneak into the playoffs this year. That likely requires adding a hitter from the outside. Without that addition, they’re still a team that could sneak above 81 wins.
This marks the time when Bob Nutting needs to start spending money.
It marks the time when Ben Cherington needs to start making serious additions to this team — the modern-day Russell Martins, Francisco Lirianos, and A.J. Burnetts.
It marks the time when Derek Shelton needs to show that he can manage to keep this team above water, absent any prolonged team slumps.
The next eight months will display how serious the Pirates are about winning.
Paul Skenes is in Pittsburgh. Jared Jones is in Pittsburgh. Mitch Keller, Bryan Reynolds, and Ke’Bryan Hayes are under contract for years.
The window is open.
Pirates Prospect Watch
Termarr Johnson continued his recent hitting in High-A on Wednesday with his sixth homer of the year. Braxton Ashcraft also made his second start in Triple-A, throwing 4.1 shutout innings. Ashcraft could help the Pirates in the majors this year, while Johnson would likely be an option for future teams in the window discussed above. You can read about both in the latest Pirates Prospect Watch.
Pirates Prospect Watch: Termarr Johnson Continues Hitting With His Sixth Homer
