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The Pittsburgh Pirates Are Failing, From Owner Bob Nutting to the Dominican Academy

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For about a week in July, it felt like baseball was back in Pittsburgh.

The Pirates were above .500. Their fans were packing the stadium, not just to see rookie phenom Paul Skenes, but to see a winning team.

With a chance to capitalize on their position in the standings, and yet another grace of goodwill given by the fans, the Pirates opted to conduct business as usual.

Here we are in mid-August, with a story that defines this franchise: The Pirates have entered a massive losing streak, after taking a cheap route at the deadline, while starting to sell their fans that next year will be better, as those fans start to tune out for football season.

It takes a lot of benefit of the doubt to assume next year will be better. This organization doesn’t deserve the benefit.

The Pittsburgh Pirates are the best representation of failure in professional sports.

Unfortunately, this failure is like a cancer that has invaded the entire body of the organization — from the head to the heart to the bones to the bowels. The options are to either watch them slowly die, or take extreme measures to remove every ounce of the cancer, and hope there’s life on the other side.

Even more unfortunate is that only one man can make the necessary changes, and those changes won’t happen until Bob Nutting decides that he no longer wants to be a mediocre owner. Or, the unlikely scenario that he sells the team.

Bob Nutting is Comfortable Being Mediocre

Back in February, Stephen Nesbitt and Ken Rosenthal wrote a piece in The Athletic titled “Why the Pirates keep losing: ‘Comfortable being medicore’“. The article provided a summary of what any long-time fan knows about this organization. There was one new piece of information.

The Pirates upgraded their facilities at Pirate City in 2016, adding a new performance center and expanding their clubhouse. I was one of the credentialed media who received a tour through the new facilities at the time, along with Nesbitt, who is one of the best writers and reporters who has emerged from Pittsburgh in the last decade-plus. The Pirates happily showed off their new investment, while leaving out an important detail.

According to Nesbitt and Rosenthal’s reporting, the $8 million upgrades were taken from the baseball operations budget, despite General Manager Neal Huntington requesting additional money from Nutting. The money was ultimately taken from the Major League payroll.

You’ll start to notice a theme throughout this article, and it’s a theme that Pirates fans are familiar with.

In 2015, the Pirates had the second-best record in baseball. Their misfortune was going up against the team with the third-best record, and the best pitcher in the game at the time. The Pirates were eliminated in the Wild Card game for the second year in a row, in their third year making the post-season.

That offseason, the team still had Andrew McCutchen under team control for three more seasons. Gerrit Cole was under team control for another four years. Baseball America rated them with the 11th best farm system, with a lot of their best prospects set to arrive in 2016.

With a team that was already a strong contender, and with a chance to build upon the contending window with additional payroll at the Major League level, the Pirates once again went the cheap route, while diverting money to their new performance center.

Charlie Morton was salary dumped. Neil Walker was traded for Jon Niese, in a deal that aimed to address a pitching need while also maintaining a similar salary level. They didn’t spend more than $4 million per year on a single free agent, with John Jaso at first base being their biggest signing.

Pirates fans were told that this was going to be a “bridge year”, waiting for the prospects to arrive to return them to winning, while hoping for the best from guys like Jason Rogers and Jake Goebbert.

In the process, they watched J.A. Happ sign elsewhere for three years and $36 million, after striking gold with the right-hander at the previous trade deadline in another value addition.

We can 2024-quarterback those deals in a lot of ways. Morton was hurt most of 2016, before starting his revival in 2017. Josh Harrison took over for Walker. Niese was horrible, but Happ continued his resurgence that started in Pittsburgh. What’s clear is that Huntington was hamstrung financially, leading to an offseason that was anything but exciting for Pirates fans coming off the best season in decades.

At the time, I gave them the benefit of the doubt that they could continue to find value pieces without spending money. I also had the Pollyannaish belief that prospects could arrive and immediately save the day.

Years later, I’ve grown, matured, and realized the error of my thinking. I’m not sure the Pirates have done the same.

*****

Bob Nutting has an extremely low risk profile. It’s well reported that the Pirates don’t spend unless they have the money available. This is opposite of almost any business, where you need to invest in the product to attract customers. For years, Pirates fans have been told that if they show up, the Pirates will spend.

They showed up in 2015. The attendance that year was just under 2.5 million, which is a franchise record.

Nutting responded by going the cheap route. He took money from the Major League payroll and used it for a capital investment. If he were to ever sell the franchise, the upgrades to Pirate City would only raise the value of that future sale. In the process, he sacrificed the final years of McCutchen and Cole to a feeble attempt at winning without spending money. Rather than supporting the core group of performers in Pittsburgh, he left the front office hamstrung to piece together value additions and prospect miracles to support a former MVP still in his prime and a pitcher who would go on to be the best in the game elsewhere.

It’s important to note that Nutting doesn’t need to operate like a normal business. The Pirates receive more in revenue sharing each year than they spend in MLB payroll. As long as the payroll stays low enough, Nutting can guarantee a profit, or at least break even, without selling a single ticket. Sure, the part-time employees at the stadium might see their hours cut, and the fans might wait three innings for a hot dog with the slower service, but the important thing is that the Pittsburgh Pirates franchise remains in the hands of the Nutting family.

That’s important, because no other owner would ever think to dedicate their time and energy to Pirates Charities. I hope you detect the sarcasm.

I hope you can also imagine an owner who would be able to provide charity to the community while also providing a respectable entertainment organization for the same community to take pride in — and Pittsburgh takes more pride in their sports teams than any other community.

My own view is that Nutting has had everything handed to him. His great-grandfather started the newspaper conglomerate that he currently oversees, with over 100 papers across America. The Pirates were purchased by his late-father, and the only investment the Nutting family has ever made in this team has been to increase their ownership share by buying out minority owners.

Nutting has never had to win anything. He’s been handed control over massive industries, and he’s used his leverage to secure his role. That role? The single most important piece of the Pittsburgh Pirates’ chances of success.

As long as Bob Nutting is allowed to suck on the teat of Major League Baseball’s revenue sharing program, while only focusing on maintaining his position as owner with a risk-free approach that involves not spending money on Major League payroll, then the Pirates will continue to be the best representative of failure in professional sports.

No amount of charity can erase that legacy.

Unless a change in operations is made, the Nutting family will be synonymous with failure. The legacy that he passes on to his daughters when they eventually take over the team will be a legacy of failure.

In all honesty, I’m not even sure that Major League Baseball cares if the Pittsburgh Pirates succeed.

Travis Williams Leads a Massive Conflict of Interest

In November 2019, Nutting hired Travis Williams as the new president of the Pittsburgh Pirates.

Williams was previously the chief operating officer of the Pittsburgh Penguins. He was involved with the new arena development, and worked on their television deal with AT&T SportsNet.

In late 2021, the Penguins were bought by Fenway Sports Group, which also owns the Boston Red Sox, Liverpool in the Premier League, and other sports franchises.

Last year, Fenway Sports Group purchased AT&T SportsNet, after Warner Brothers Discovery Sports began unloading their regional sports networks. The Pirates, led by Williams, entered a deal with Fenway as co-owners of the new SportsNet Pittsburgh. The Pirates are minority owners, with Fenway owning 80% of the network. The network launched on January 1st this year.

Jason Mackey at the Post-Gazette had some great reporting on the deal at the end of last year. Within that article, Mackey noted the likelihood that the Red Sox would profit off the Pirates new local TV deal. Williams downplayed the conflict of interest, while noting that Major League Baseball saw no conflict.

This is also a league that changed the draft after the Boston Red Sox complained that the Pittsburgh Pirates spent too much money on amateur bonuses in 2011 when they signed Josh Bell for $5 million. Why would they care if the Red Sox were earning money from the Pirates years later?

The Pirates’ president also downplayed the impact that a local TV deal has on the Major League payroll. From the Mackey article:

“I don’t think payroll is a product of our television deal,” Williams said to the Post-Gazette. “Payroll is a product of many different things in terms of where we are in building a team. As I’ve mentioned before, the revenue that comes from these types of deals, whether it’s this or a sponsorship or a jersey patch, any of those topics, that’s part of the overall revenues that we use to invest in the organization, areas where we’re going to make a difference.

“That could be player development, research and development for drafting or trades, any number of things. I don’t tie one deal or one relationship specifically to payroll. I don’t think our fans should, either.”

First, this is asinine.

There has been no greater impact to Major League payrolls over the last decade than the local TV deals.

The Los Angeles Dodgers became a powerhouse after inking a local TV deal that pays them in excess of $250 million per year. The Houston Astros became perennial contenders in payroll standings and the real standings, after landing a $70-80 million per year local deal. The Pirates previously had a deal for $50-60 million per year from AT&T SportsNet, and their new network is likely to pay them less. However, they should be making more than the $20 million per year under the former local TV deal that expired in 2019.

That deal was negotiated by former president Frank Coonelly, who came to the Pirates from MLB’s labor relations department. Coonelly’s former job was aimed at keeping player salaries low. After leaving the Pirates in 2019, he returned to the same department. But not before negotiating a bad TV deal that hamstrung the Pirates for a decade, right before the boom in local TV deals that Coonelly should have known was coming from his former position.

Coonelly and Williams both have carried the same characteristic of gaslighting Pirates fans on the way team revenues work. Both are affluent, corporate-speaking white men in suits, with zero knowledge of running a baseball team. Their time as Pirates presidents are defined by telling Pirates fans the right way to think about the business. And the right way is always to direct the attention away from low payrolls, no matter how much additional revenue comes into play.

“I don’t tie one deal or one relationship specifically to payroll. I don’t think our fans should, either.”

The figures aren’t known for the new network, but the Pirates are likely to make more money from this deal than their deals in the past. MLB national revenues have gone up since 2019, which means the Pirates are receiving more in revenue sharing than in the past. Yet, the Pirates remain in the same payroll range they’ve existed at for over a decade.

It’s completely illogical to suggest that these deals don’t have a relationship to payroll. What Williams says is true, that it all should be counted as revenue. But every time you see a Sheetz patch on a jersey of a hitter watching a fastball go right down the middle for strike three, you have to wonder where that money is going if it’s not going to payroll.

The MLB Players Association filed a grievance against the league in February 2018, which included individual claims against the Pirates, Rays, Athletics, and Marlins. The grievance against the league was dropped in 2020, but the MLBPA has refused to drop the grievance against the Pirates. Nor should they.

Despite an increase in revenues, Pirates fans are left hoping that the owner will decide to spend on the Major League team at a time when added payroll can push them into a winning position. The added payroll would also push them into record-spending levels, which seems appropriate from the added revenues.

Instead, it’s more likely that their suit in the president position will corporatesplain to all of the idiot blue collar Pittsburgh fans exactly how payroll is only a small fraction of the costs of running a Major League organization. And the MLBPA will have no reason to drop their grievance.

Ben Cherington May Be Hamstrung, But…

The first move that Williams made was hiring a search firm to select the next General Manager. The firm, Korn Ferry, selected former Red Sox General Manager Ben Cherington.

Cherington was the pick of a finalist group that included Pirates interim General Manager Kevan Graves, Brewers assistant GM Matt Arnold, and Houston Astros director of player development Pete Putila.

Graves is one of the smartest people I’ve ever met, and is currently an assistant GM under Cherington. Arnold took over as the Brewers General Manager ahead of the 2021 season. They finished first place in the NL Central the following year, second in 2022, first in 2023, and they have a commanding lead of the division this year. Putilla was hired as the General Manager of the Giants last year, and they currently have a winning record for the first time since 2021.

Korn Ferry also selected Chaim Bloom as the Red Sox General Manager in late 2019. After fifth place finishes in three of four seasons, Bloom was let go by the Red Sox. The accolades of Korn Ferry also include putting Rob Manfred in the MLB Commissioner’s seat, which is a move that doesn’t need further explanation to any baseball fan.

Ultimately, Williams and Nutting turned to Korn Ferry to make their decision.

Cherington was hired to fix the development problem that prevented top prospects from having success in Pittsburgh. He was ultimately hired to bring winning back to the Pirates. In year five of his time as General Manager, the Pirates are in fifth place for the third time, with two other fourth place finishes.

The farm system Cherington inherited was rated 24th overall when he took over heading into 2020. After five years of tanking and picking in the top ten of the MLB draft, the Pirates have the 27th best farm system. The Pirates have not only been one of the worst teams for five seasons, but they also have nothing to show for the tanking — outside of a team built on Neal Huntington acquisitions, and the lottery ball gift that was Paul Skenes.

This has been exacerbated by his trade history, which largely failed during the tear-down and rebuild period.

READ: Williams: Ben Cherington’s Pittsburgh Pirates Trade History – The Eras Tour

One thing I didn’t like that Cherington did was when he insisted that the Pirates weren’t going through a rebuild, but instead a “build”. By obfuscating the clear assignment of the General Manager into obscurity, Cherington was setting his own goalposts deep in the forest where no one could find them. Actions are always stronger than words, though, and results trump all.

For the life of me, I can’t see much that has been built.

The amateur scouting department, which was largely built under Huntington after the 2008-2010 drafts, remained largely intact until this year. Cherington kept the same group together for two first overall picks, despite growing evidence of an inability to identify hitting talent. That evidence includes Cole Tucker, Kevin Newman, Will Craig, and Travis Swaggerty as first rounders between 2014 and 2018.

The development process has changed under minor league director John Baker, who was hired by Cherington in late 2020. I give Baker’s individualized approach big credit to the recent pitching success from prospects entering the majors. No longer are the Pirates taking a one-size-fits-all development approach for their pitchers. A lot of this development is outsourced to training facilities, and the hitting development has been non-existent.

Cherington gets credit to the pitching development for ignoring long-term payroll implications by calling up Jared Jones and Paul Skenes early this season. I do think it makes an impact to players when they know that the organization won’t penny-pinch every potential dollar away from their efforts.

The other biggest impact under Cherington has been an influx of female leadership — from Assistant General Manager Sarah Gelles all the way down to minor league coach Stephanie Lombardo. It’s important to have the female perspective in a male-dominated industry for many reasons. One of those reasons is that every human being contains the masculine and the feminine, and not every baseball player will respond to the classic, almost toxic-masculine approach to coaching and development that has historically prevailed in this game.

All of that said, Cherington has made no serious effort to upgrade the Major League team in five seasons, outside of the same value-seeking approach and reliance on prospects that ended the last Pirates’ contending window.

When the Pirates were contending in July, he waited until the last minute to make a series of moves that ultimately reduced payroll, and which only improved the team by raising the floor with added depth.

Pirates fans are left once again hoping for next year, praying on the prospects, and wishing that the General Manager would spend money to add an impactful addition, rather than a slew of value-based lottery tickets.

All of this ultimately goes back to Nutting. It’s very possible that Matt Arnold wouldn’t have had the success with the Pirates that he’s had with the Brewers, due to the way Nutting hamstrings his General Managers. Cherington has been hamstrung, and the proof is the inability to add salary to this year’s team. But…

“Nothing someone says before the word “but” really counts.”

The but, in this case, is that Cherington has seen his farm system decline to one of the worst in the league in five years, while hoping that a current fifth-place team will be a real contender next year — without the ability to really spend on Major League payroll like a real organization.

It’s an impossible situation for any General Manager, I fully acknowledge. But, Cherington hasn’t done a job that would warrant much benefit of the doubt that being hamstrung by Nutting is the sole issue.

Derek Shelton Just Needs to Manage Better

After every Pirates loss, manager Derek Shelton answers the media questions with some form of “He just has to play better.”

It’s a variation of a line that has been used over and over again since Shelton was hired by Cherington ahead of the 2020 season. After five years of fourth or fifth place finishes, you have to wonder who is going to get the players to play better, if not the manager?

When the team was fielding the likes of Josh VanMeter, you could give Shelton a pass for the team Cherington gave him. The last two years, the Pirates have opened their season with a hot start, only to quickly fall into a prolonged losing stretch that ultimately decided their fate as a losing team.

Shelton’s team lacks energy and confidence, and the same can be said for his managerial approach. He will occasionally charge out to the field to argue a meaningless call, but the team never seems fired up. Shelton never seems to have the answers after the losses.

After the winning stretch to open last season, Shelton was extended by Cherington. There’s no public information on how long that extension runs, but nothing has indicated that Shelton’s job is in jeopardy by Cherington. We’re also beyond the point where you can blame the Pirates’ Major League woes on a tanking team approach by the General Manager.

Shelton just needs to manage better.

Yet, the Pirates are currently on a nine game losing streak, which has quickly dropped them out of their chance to contend in 2024, the fifth season under Shelton and Cherington.

The Pirates Entire System Has a Hitting Problem

One of the biggest reasons the Pirates are losing this year is due to a complete offensive ineptitude, which extends throughout their entire system.

Hitting coach Andy Haines has led the Pirates to a bottom-five offense in baseball over the last three years. This follows three years as the hitting coach with Milwaukee, where Haines once again oversaw a bottom-third offense.

The biggest success stories have come from players turning away from Haines.

Last year, Ke’Bryan Hayes turned to Altoona hitting coach Jon Nunnally for help at the plate, and the result was the best offensive output of Hayes’ career. The Pirates validated their long-term, Gold Glove winning third baseman by firing Nunnally and sticking with Haines.

This year, Rowdy Tellez got off to a start that made him one of the worst hitters in baseball for two months. Tellez went outside the organization for help, and has since been one of the top five hitting first baseman since the start of June.

I’ve yet to hear of a success story involving Haines. The closest is an MLB.com report that credits Haines for a meeting that showed Nick Gonzales had drastically changed his swing since college. The real work came solo, with Gonzales building a hitting facility in his backyard over the offseason to find a new stance.

Crediting Haines with spotting how much Gonzales’ swing has changed is damning. His swing changed for the worse in the Pirates’ development system.

That system has not produced any hitting prospects of note. All of the pure hitters have struggled. All of the power hitters have been three-outcomes guys. Every year there’s a breakout in the hitter friendly park in Greensboro, but after extensive time in Double-A, those breakout bats eventually fall back to Earth.

The current depth from Triple-A relies on two minor leaguers the Pirates acquired from other organizations at the deadline.

Had the Pirates made a change to their hitting approach earlier this season, they might have had a better chance at contending this year. Their young pitching has been elite, but the offense has been inept. That same ineptitude has led to the low minor league system rankings.

At the very least, the Pirates need a change to their hitting approach, all throughout the system.

The Development Only Works For American Pitchers

When Cherington took over, the Pirates were seeing a trend where their once heralded prospects struggled in Pittsburgh, only to have success elsewhere.

They’ve hopefully fixed that issue on the pitching side. The hitting side leaves a lot to be desired.

Pitching is a game of confidence. The pitcher is the most important player on the field. Every other player reacts, but the pitcher is the only player who is proactive. Every play begins with a pitch being thrown, and only the pitcher and the catcher know the intentions of the pitch. Only the pitcher can control the execution of the pitch.

Developing that level of confidence to succeed on the mound at the Major League level is no easy feat. Don’t think I’m underselling the massive impact made with the development improvement of young pitchers into Pittsburgh.

That said, it’s a problem that the only people having success reaching the majors, and the majority of the top prospects, are American-born pitchers.

The international side of operations has produced nothing.

The top international signing in Baseball America’s latest Pirates system rankings is number 12 prospect Tsung-Che Cheng, who is struggling at the plate in Altoona. Omar Alfonzo ranks 20th overall, and he’s having a promising season in the lower levels. Both of these players were signed under Huntington.

This is another case where nothing has really been built under Cherington.

The international scouting group is largely the same as it was when Huntington left. The expansions to the Dominican Academy — another capital investment by Nutting which likely took away from MLB payroll over the years — happened under Huntington, and has produced nothing but the promise of raw ability and limited success in the lowest levels of the minors.

When a team can’t spend on Major League free agents, they can’t afford to completely cut off an area of talent acquisition. The Pirates have had over $25 million in bonus money to spend on international free agents under Cherington, and that has yet to lead to a top 20 prospect in five years.

By comparison, the Pirates signed Gregory Polanco in 2009. By the start of the 2013 season, four years after he was signed, he was one of the top 100 prospects in the game. Polanco never lived up to his hype, but at least there was hype.

There’s no Polanco in this system. There’s no Starling Marte. There isn’t even a Luis Heredia who can dash the hopes of fans seeing another future ace turn bust. Despite all of the international spending over the last five years, the only thing the Pirates have to show for it is a signing ceremony with the media, touting the life-changing impact of the signings themselves.

This is once again the Pirates focusing on a form of charity.

Every international player signed by every team has a life-changing impact. Having an organizational impact would be preferred. The Pirates have taken a step back with their international signing results since parting ways with Rene Gayo in 2017. That parting was over Gayo’s bonus-skimming, and it was deserved, but the results since have paled in comparison.

Add international scouting director Junior Vizcaino to a long list of problems with an organization that is failing from top to bottom.

What Can Be Done?

Nutting. I mean, nothing.

This all starts from the top, and Bob Nutting has been adamant that he’s not going anywhere. He could sell the team today, and no one in his family would have to worry about finances for a few hundred years — outside of some Vanderbilt-level ineptitude in spending.

As long as Nutting is the owner, and as long as he’s comfortable with a ceiling of mediocrity that comes from a risk-averse approach to spending on a winner, the Pirates will be hamstrung.

Ben Cherington has not done a good job as the General Manager in five years, arguably taking the organization backwards in more ways than he’s built up the franchise. But, with Nutting as the owner, it’s hard to imagine any alternative doing better. More importantly, it’s hard to imagine Nutting adding a General Manager who would require him to change his ways.

Derek Shelton doesn’t seem to have the answers to maximize what Cherington has provided with his limited funds. The players just need to play better, but performance reflects leadership.

Andy Haines oversees a disastrous hitting program, which if upgraded, would improve the Pirates in a crucial way. The hitting development throughout the minors could also use improvement, so that the prospect rankings aren’t dependent on pitchers from one avenue of amateur talent acquisition.

The international scouting approach should also be reviewed, as there’s no example from the Latin American countries of the Pirates landing a top prospect in years.

The Pirates look like they need an organizational overhaul in more ways than they look close to contending for the foreseeable future.

Unfortunately, that overhaul wouldn’t extend to the owner. For that reason, it’s probably best to hope that they overhaul their hitting approach this offseason, find a manager who can maximize a long-shot roster, and hopefully increase spending to add at least one impact player for the coming years — rather than relying on prospects to do it all.

Playing in Major League Baseball is difficult enough. Putting all of the hopes of an organization on those young, developing players is added pressure that is likely a large part of the historical development problems in Pittsburgh. The alternative would be Nutting finally investing money in Major League payroll. Continuing down the cheap, MLBPA grievance route would be continuing a failing strategy.

And the Pirates are exceedingly the definition of failure in professional sports.

That’s the legacy Bob Nutting is building.

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Tim Williams
Tim Williams
Tim is the owner, producer, editor, and lead writer of PiratesProspects.com. He has been running Pirates Prospects since 2009, becoming the first new media reporter and outlet covering the Pirates at the MLB level in 2011 and 2012. His work can also be found in Baseball America, where he has been a contributor since 2014 and the Pirates' correspondent since 2019.

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