In May 2016, the Washington Nationals signed Stephen Strasburg to an extension. The deal was for seven years and $175 million, with a player-friendly opt-out after the third or fourth year. Strasburg was set to be a free agent following the 2016 season, and this extension kept him in Washington.
He ended up opting out after the 2019 season, but not before leading the Nationals to a World Series that year. The 2016 extension ended up paying Strasburg $15 million per year in 2017-2018, along with an increase to $35 million in 2019. Out of that 2019 total, $30 million was deferred without interest, paid as $10 million installments on July 1st, 2020-22. He also received a $10 million signing bonus, paid in 2019.
In total, the Nationals got three free agent years from Strasburg for $75 million, though the contract structure paid him $15 million per year for those years, along with $10 million per year in the three years after he opted out.
He signed another extension after 2019, which didn’t go so well for Washington. However, that first extension should be a model for any team trying to lock up an ace pitcher beyond their team-controlled seasons.
*****
Paul Skenes is a litmus test for the entire Pittsburgh Pirates organization.
They made the right decision one year ago when they drafted the generational pitcher over a group of hitters.
They didn’t penny-pinch when they called him up this year on May 11th, ignoring the Super Two cutoff that may have saved them a lot of money in the long-run. His performance this year in extended work will likely make him a finalist for the Rookie of the Year award, which would give him a full year of service time. Either way, Skenes is eligible for arbitration after the 2026 season. If he finishes top two in the Rookie of the Year voting, he will be a free agent following the 2029 season.
We’re only ten starts into the MLB career of Skenes, and a lot can happen between now and 2029. The most likely scenario is that the Pirates will eventually be faced with a financial demand they’ve never seen. Skenes will be a free agent for his age-28 season, and will command a contract that will no doubt be the biggest in Pirates franchise history.
The Nationals showed the way with Strasburg. For one, I don’t think anyone needs to really worry about a Skenes extension until he’s close to free agency. The Nationals took some risks with a player-friendly deal, and crafted their deal in an affordable way, getting their ace for $25 million per year. The Pirates should eventually be able to do the same, if they’re willing to pay the money.
The question is will the Pirates spend the money when the time comes?
Spend Nutting, Win Something
Will the Pirates spend the money?
That’s the question that surrounds everything with this franchise.
It’s a question that deserves to be asked. Actions speak louder than words, and there are no actions that suggest optimism toward owner Bob Nutting spending what it takes to win. Nutting has said there are funds available for the upcoming trade deadline, and their current rebuild is structured in a way to require franchise-record spending every year going forward.
The Pirates have made commitments to spend in a larger way than they ever have before. Bryan Reynolds was signed to an extension through the 2030 season, paying him $15.25 million per year for the final four years of the deal. Mitch Keller was signed through the 2028 season, receiving $15-20 million per year from 2025-2028. They have a front-loaded deal with Ke’Bryan Hayes, which pays him $7-8 million per year through 2029.
If the Pirates are going to compete in the next three seasons, they’ll do it while paying those three players about $35-40 million per year. If those players make up a quarter of the payroll, you’re looking at $140-160 million ranges for a competitive team.
That should be accomplishable for a small market team. The Reds, for example, have spent to the $140+ million range several times over the last decade.
If you’re doubtful that Nutting will spend to those numbers, your doubt is valid.
What Exactly Has Been Built?
The rebuild under Pirates General Manager Ben Cherington has not gone well, if I can give my honest opinion.
We’re in the fifth year of this rebuild, which Cherington branded a “build” out of the gate. I didn’t like that declaration, as it undermined all of the work that Neal Huntington did in his time as the previous General Manager. It’s also difficult to see any sign today of what has been built under Cherington.
The biggest example of the lack of an original build comes this week. The MLB Draft is this weekend, and this will be the fifth draft under Cherington. The amateur scouting department for the first four drafts was largely the group that was built under Huntington. That department was overhauled after the 2008-2010 drafts, and has shown one big trend since then: The ability to find elite Major League pitching.
Cherington left this group intact, and they’ve continued finding elite pitching.
- Brian Tracy joined the organization in 2009, and added Jared Jones in the 2020 draft. He’s also the scout who originally found Connor Joe.
- One of the final hires under Huntington was Cam Murphy in 2019, who has since signed Carmen Mlodzinski and current top prospect Bubba Chandler.
- Wayne Mathis was the signing scout for Paul Skenes, and he’s also added Shane Baz since joining the organization in 2016.
The success this season is largely due to the ability of the amateur scouting department built by Huntington.
That department does not have the same track record with finding hitters, and it has taken Cherington four drafts and two first overall picks to make a change at the top. Following the drafting of Skenes last year, the Pirates added Justin Horowitz from the Red Sox to be the new amateur scouting director, replacing Joe DelliCarri, who had been on the job since 2012. It’s a curious move to make this change after a stretch of picking first overall twice in four years, with two other top ten picks. It’s especially curious to make this after drafting Skenes, who wasn’t seen as the consensus number one overall last year. Perhaps the change to Horowitz will lead to a better selection of hitters, while maintaining the pitching quality.
It’s not all about drafting. This organization had elite pitching in the past, and those pitchers never succeeded in Pittsburgh. If Cherington deserves credit for one thing, it’s fixing the development flow of pitchers.
I credit a big part of that to the individualized development plan under minor league director John Baker, who was hired by Cherington to create a better development system. The Pirates in the past would teach all of their pitchers the same approaches — get outs in three pitches or less, work off the fastball to an extreme percentage, add a sinker to give deception on a fastball-heavy approach, and so on. There was never a confidence given to the stuff the pitchers actually had.
This was apparent with Tyler Glasnow. The Pirates spent a lot of time trying to develop a changeup so that he could have success in the majors, before he even had a chance to fail in the majors with his existing stuff. They were inherently projecting failure onto Glasnow by forecasting how he would fail in the future without more than two elite pitches, and trying to fix that forecasted problem ahead of time. Today, Glasnow is one of the best pitchers in the game, and he doesn’t throw a changeup.
Like many pitchers who left the Pirates to find success elsewhere, the success came for Glasnow when the Rays just told him to trust his stuff. The Pirates could find pitching talent in the past, but they couldn’t develop the confidence in those pitchers needed to be successful in the majors.
By comparison, Jared Jones went to the majors this year on Opening Day with two plus pitches, and the same need to develop more pitches in the long run. The Pirates didn’t hold Jones back until he developed the pitch that will prevent him from ever having issues in the majors. They just let him work with his elite duo, and a drive to continue improving in the majors.
I can’t say that Cherington or Baker have built a good development system. I think they’ve just gotten out of the way of their best players. Most of the positive developments that have taken place have been separate from the coaching in the system. That’s not to say that there haven’t been additions within the system.
For example, Skenes didn’t need Major League confidence from the Pirates. He had that before he was drafted. They did work with him to give him a splinker, which has become one of the best pitches in the game. His rookie season would be looking a lot different without that pitch.
That said, it was minor league pitcher Thomas Harrington who helped Jones take a step forward with his fastball. In my reporting throughout the minor league system over the last few years, I’ve heard a lot of stories about players learning from each other. I’ve also heard a few stories of pitchers learning from Harrington. This is part of the open learning system created by Baker, where players can go with any avenue to improve their game.
Harrington, by the way, was signed by scout Mike Bradford, who was added under Cherington in 2021. Cherington has outsourced the hiring process to each individual department, so this was still an extension of the Huntington scouting department led by DelliCarri. Any scout hired going forward under Horowitz will be part of the scouting department that Cherington is building.
There has been a lot of work by Cherington in building up the analytics department to be used by the players. The Pirates were strong with analytic study in the past, but largely kept the information from the players to use. There has also been a lot of work to build up the pro scouting department, which has led to some sleeper additions to fill out the roster.
The problem right now is the Pirates have no hitting. They have a flawed philosophy, a complete-pendulum-swinging excess reliance on analytics, and they still haven’t shown the ability to draft hitting talent on the level that they draft pitching talent.
The flawed hitting philosophy likely originates with Cherington, and is played out through hires such as hitting coach Andy Haines. The Pirates now put too much emphasis on data, using it to form a strategic passive approach that seems detrimental to success. This is shown by the actual success stories.
- Nick Gonzales, for example, took it upon himself to build a hitting facility at his home this past offseason, and worked on a new swing at the facility.
- Rowdy Tellez has seen a revival after a discussion with his father and an adjustment with his approach.
- Ke’Bryan Hayes had his best offensive stretch last year while working with minor league hitting coach Jon Nunnally in Altoona. Nunnally was fired by Cherington in the offseason, with the move largely believed to be a response to Hayes showing preference to the Double-A hitting coach over Cherington’s Major League hitting coach.
Nunnally inherently knew hitting, without having to look at the data to strategize for a specific hitter. His approach was a true individualized development plan for each player. What Nick Gonzales is doing today is what Jon Nunnally was saying he should do two years ago in Double-A.
My concern is the Pirates have freed up their pitchers to an individualized development approach that allows them to build confidence in their stuff, while the hitting has gone the opposite direction.
The hitting approach seems anything but individualized, and doesn’t seem like it gives confidence to players who are already in a confidence-destroying situation, where the best hitters fail 70% of the time.
In year five of the rebuild under Cherington, I can’t find proof of anything that has been “built” that wasn’t here before. The pitching development has been adjusted in a positive way, while the hitting has taken a step back that I didn’t think was possible.
The amateur scouting remained the same. The development system shifted from very little applied analytics to perhaps too much applied analytics. The pro scouting has been overhauled, but Cherington largely whiffed on his rebuilding trades. The pro scouting success stories are at the level of Ryan Borucki as a waiver claim, or Joshua Palacios as a minor league Rule 5 addition. These are complements to a winning team, but the pro scouts aren’t finding players who can eventually join Keller, Reynolds, Hayes, Skenes, Jones, and the rest of the window that is forming around Neal Huntington additions, or additions under the scouting department built by Huntington.
The one change that Cherington has made that I really like is the incorporation of more female leaders throughout the organization. From assistant General Manager Sarah Gelles, to on-field development coaches like Bradenton’s Stephanie Lombardo, I believe there is a value in incorporating the female mind into a male-dominated space. Aside from giving young women in Pittsburgh examples of how they can reach careers with executive abilities, I believe there is a specific benefit to development here that I don’t want to break down in this article.
Started From the Bottom, Now We’re Here
Despite Cherington’s rebuild being a bit of a disappointment, the Pirates are in position to contend for the rest of this decade. They have the makings of an elite rotation, with even more quality pitching on the way in the upper levels. I think that matters a lot.
Cherington deserves some credit for that, and I think the credit goes toward the improvement of the pitching development during his time.
The fatal flaw I see with Cherington is that he takes too long to correct mistakes, and often keeps betting on the same losing hand, hoping to eventually see the winner he expected.
The player example of this is Rowdy Tellez. The Pirates look justified today in keeping Tellez to help lead them to wins in June and July. How many games were lost in April and May to get to these wins?
How many games might the Pirates lose in April/May 2025 if Cherington’s next free agent gets off to a similar slow start?
The systemic example falls to the hitting. The situation with Nunnally and Hayes last year showed a correctable flaw in the system. The Pirates need more hitting coaches who actually know how to coach up hitters, rather than telling them the best selective strategy for success, according to the analytics. Instead, Cherington loaded the MLB staff up with even more presence of analytics. I cringe when I see a tablet in front of a player who is already hitting in the current game. It shows a complete lack of understanding of the confidence hitters need to have success.
The Pirates are good at identifying confident pitchers, and they’re now good at allowing that confidence to shine through to the Majors.
I think they’re looking for the same confidence from their hitters, and that’s a mistake. The hitter confidence is opposite of pitchers. Pitchers have a natural advantage with the element of surprise. They can plan an attack against hitters. A hitter can only react and defend their zones against the attack. When a hitter starts to go on the attack with pitcher confidence, you get a Henry Davis situation, where a young player tries to crush every single pitch, not respecting the advantage of the Major League pitcher.
The problem I see right now is that the Pirates clearly need hitting, but I’m not sure that I trust the Pirates to add quality hitting under Cherington.
Will their pro scouting department be able to identify a quality hitter?
Can their coaching staff and approach allow the hitter to maintain the defensive confidence needed to succeed?
Every hitter the Pirates have added this year has put up the worst results of their careers. Their top hitting prospects throughout the system have struggled this year. The success stories over the last two years have come from turning away from the Major League coaching. Whether pro scouting or coaching, there’s a fatal flaw in the system on this side of the game. And Cherington has been dreadfully slow in fixing it.
That’s not to say the Pirates shouldn’t add hitting at the deadline. They need a hitter, even if Tellez and others rebound. They need a hitter, even if it’s not a guy who will be here beyond 2024.
Paul Skenes could win the Rookie of the Year award and get a full year of service time in 2024, making him a free agent after 2029, instead of after 2030. The Pirates are within striking distance of a playoff spot this year, in what will likely be one of six years they know they have Skenes. This is a team that needs to start pushing in the chips toward winning.
Bottom Line Bob
I respect the difficult position that Cherington is in, because he’s never going to have a top budget to work with. Even if the Pirates eventually spent to the $140-160 million range, that would put them 14th-17th in the current season. That’s still an average or below-average payroll, but up from one of the lowest totals in the league.
The problem is that we know the intentions of the people above Cherington.
Team president Travis Williams, for example, has been quoted with this belief on the fan experience:
“You can overcome a bad outcome on the field with a great fan experience,” Williams told The Athletic. “You cannot overcome a good outcome on the field with a bad experience.”
The second part might be true, but that doesn’t mean the first part is also true. In the city of Pittsburgh, with the history of the Pirates, I don’t think there’s a combination of items you can put on a hot dog that would feed the fans who are starving for a winner on the field.
Bob Nutting has made it very clear that his intention is to keep the Pirates in his family. He wants his daughters to one day own the team in the same way he was handed the team by his father. Nutting routinely points to the team efforts in the community, via charity and other events held at PNC Park, to downplay the impact of winning, or the need for the Pirates to provide winning to justify his ownership route.
The reality is that Major League Baseball offers Nutting a risk-free way to make profits. He might not be withdrawing those profits from the team each year, but every year Nutting remains an MLB owner, his valuation goes up as the franchise valuation increases. It doesn’t matter if he wins, or how much he spends, as long as he doesn’t take any big losses.
If Nutting sold the Pirates today, then his daughters, and their daughters, and their daughters, and their daughters, and their daughters, and their daughters, and their daughters would all be set to survive comfortably for longer than Major League Baseball will be around.
This is about control, and mostly, control of the masses.
Nutting comes from a family that has owned newspapers since the late 1800s, with a current roster of over 100 papers across the country. That’s a lot of responsibility to accurately inform the masses in many states of what is happening in the world. So many people have their realities shaped by the reporting and opinion from Nutting’s papers. From there, the Pirates are a ship that houses hundreds of employees, perhaps into the 1,000+ area, while providing an entertaining escape for millions. The jobs created by Pirates baseball — including my own self-created independent blog, which you can support on Patreon — range into the thousands. Nutting has control over that, even if he doesn’t have control over every individual.
If the Pirates continue losing, I can tell you this site wouldn’t survive. The businesses around PNC Park would get less traffic and employ fewer people. Anyone selling Pirates merchandise would see a hit. There’s a massive impact the Pirates make financially, and the impact is bigger when the Pirates are winners.
Nutting has money to spend. The problem is that he is incredibly risk-averse, and the Pirates need to spend strategically. If the Pirates spend big in 2025-2027, and they don’t win, the fans aren’t going to show up to watch the higher payroll. They’ll call for Cherington to be fired over the bad moves, and they’ll tell Nutting to spend in a better way before they return en masse.
And it’s likely that while Nutting can spend, he has very few bullets to use before he needs to cash out, set his family up for life, and give up control of this massive influential industry to someone else. In that scenario, it would hopefully be someone who treats charity and employee hospitality in the same positive way as Nutting, without trying to make that seem like the entire purpose of owning the Pittsburgh Pirates baseball organization.
Nutting does the bare-minimum when he focuses on charity, sends his athletes into the community for events, or treats his employees with the personal respect you’d find in a business back in the 60s/70s — when workplaces were more family/community centered, rather than cold profit centers. These are admirable quests from him as an owner, but they’re all secondary to building a good baseball team that people want to watch. A good team would only increase the ability to employ more good people, and provide more charity to the community.
Paul Skenes is a microcosm of how putting good talent on the field leads to increased attendance. In his last start on July 5th, the Pirates had 37,037 in attendance, which was second only to the home opener. His MLB debut on May 11th was a top-five attended game for the Pirates this year. As the legend of Skenes grows, you can expect every start to be an event that will sell a lot of tickets in Pittsburgh.
Eventually, the Pirates will need to invest in Skenes to continue giving fans a real reason to come down to the ballpark. Before that point, they will need to build a team around him, so that they don’t waste the absolute gift they received when they won the lottery to take him first overall.
That’s going to require better hitting identification and coaching than we’ve seen under Cherington. It’s also going to require more money than Nutting has ever spent on a team, to the point where he might have to risk putting himself in position where he’d need to sell the team if he failed. His family would be controlling some other industry with the money they would get from a sale if the Pirates didn’t win. There’s no actual risk for Nutting. His family would have to fuck up for generations to ever get to a point where they wonder where their next meal is coming from.
The problem that I see is that Nutting can’t be trusted to spend, despite the need to give him the benefit of the doubt for a few more years.
The bigger problem I see is that Cherington has shown clear flaws that aren’t being corrected, and might be detrimental to the quest of winning.
It’s very possible that Nutting could spend and Cherington could waste the money. It’s also possible that Cherington — whose lone winning season as a General Manager came with a top five payroll — could be restricted in his approach by the bottom-five budget set by Nutting.
This is a team that shows potential for the future.
It’s not a team that instills a lot of trust that they’ll realize their potential.
At this point, I’d say that the Pirates have the potential to win a World Series by the end of the 2029 season — while also believing that they need to make some massive adjustments to their approach to finally bring the trophy back to Pittsburgh for the first time in 50 years.
Pirates Prospect Watch
Speaking of Thomas Harrington, the right-hander struck out 11 batters while giving up one run in seven innings for Altoona on Wednesday night. Read more about Harrington and all of Wednesday’s minor league action in the latest Pirates Prospect Watch.
Pirates Prospect Watch: Thomas Harrington Strikes Out a Career-High 11 Batters
