Talking Baseball: Vol. 19

The Pittsburgh Pirates have never felt more hopeless.

The Pittsburgh Pirates being bad — as they almost certainly will be this season — is nothing new or unexpected. It is what they do, and it is basically all anybody under the age of 50 knows from them. I was born into it, I have lived it, and unless something completely unforeseen happens in the future that will probably continue to be the norm for quite some time.

Outside of three years of the Barry Bonds era in the early 90s, and three years of peak Andrew McCutchen in the mid-2010s, this franchise has been a perpetual stain on Major League Baseball when it comes to actually winning baseball games.

Forget even the World Series or National League Pennant droughts that go back to 1979 (both among the longest in baseball), just look at how little the team has actually won in the context of the regular season or the playoff rounds since then.

In the 45 years since their most recent World Series title in 1979, the Pirates organization has had just 11 winning seasons.

It has won more than 88 games in a season just FIVE times.

It has only six playoff appearances.

The only postseason success was a one-game wild-card win against the Cincinnati Reds in 2013 that was such a big deal that, 1) people were quite literally jumping off of bridges in excitement, and 2) that game is still looked at like it was some incredible accomplishment and an all-time great moment for the franchise.

In terms of actual playoff series wins, Game 7 of the 1979 World Series was the most recent time this franchise actually won a playoff SERIES.

It is almost harder to be this consistently bad than it is to be consistently good. Like, at some point you almost have to get lucky in some random year … right?

Don’t get me wrong, that wild-card season was a magical season, and the milestone moments (like win No. 82; Russell Martin holding up the baseball at home plate in Wrigley Field when he recorded the final out to clinch a playoff spot; the wild-card game itself) still stand out in a big way.

They were huge. One of my biggest sports fan regrets is not finding a way to get into that wild-card game.

But here’s the problem: Those moments only feel huge for Pirates fans because the team and the franchise have been so consistently bad for almost half of a century. The 82nd win of a season is only a cause for celebration when you’ve lost for 20 consecutive seasons. A wild-card round win is only a lasting memory more than a decade later because you have literally had no other playoff success in 45 years.

Paul Skenes, one of the few bright spots on this year’s version of the Pirates, actually addressed all of that this past week with what sounded like a passionate plea for the team to actually be good during his time here:

“It’s our job to go out and win for the city, because this is bigger than all of us. There’s a reason why Cutch keeps coming back, and specifically to Pittsburgh. There’s something about this city. We saw it last summer. We’ve seen it in the videos of the Wild Card Game. I’m tired of watching them because it was a Wild Card. The bar needs to be set pretty high. Not taking anything from those guys, the fact that that’s a golden era of recent Pirates baseball, that needs to change. We owe it to the city.”

It is an incredible comment because it is not only a second-year guy coming in and setting a higher bar than anybody in the front office ever does, but he basically said, I’m tired of you guys still talking about a 12-year-old game the rest of the league has already long forgotten about.

Hell, Skenes was 11 years old when that game happened!

His comment about it is great.

It is the exact mindset I want coming from my franchise player.

It makes me want to run through a wall when the guy takes the mound.

But the truly crazy thing about Skenes comment, and the presence of Skenes himself, is that his presence is actually — in a very unintentional way — what makes this season and the team’s short-term (and long-term) situation seem so completely hopeless.

Perhaps even more than it usually is.

Even though he has only pitched 23 games in the Major Leagues it is not a stretch to suggest he is already one of the two or three best pitchers in baseball, and probably a top-10 player overall. He is that good. His rookie season was unlike anything baseball has seen in generations, and even as the team faded down the stretch his starts remained an EVENT. Other than Sidney Crosby’s rookie season with the Penguins, I can not recall a rookie Pittsburgh athlete creating such a buzz across the city.

Given how little luck the Pirates have had with No. 1 overall picks in their history, both in terms of missing out on potentially franchise-changing players (because they were bad in the wrong year — like missing on Stephen Strasburg or Bryce Harper; or just getting it wrong like they did with Bryan Bullington and apparently Henry Davis) it is a wonderful stroke of good luck.

They were bad in the right year.

They got the right player.

It all clicked into place.

Skenes is a gift from the baseball heavens and the type of player that can not only change a franchise, but should also inspire the franchise to change the way it operates. Especially when you know, deep down, that by year six of his career he is going to be pitching for somebody else.

We have all seen this movie before, in an almost exact similar scenario.

The only other No. 1 overall pick the Pirates truly got right was when they picked Gerrit Cole in 2011, watched him blossom into a front-line starter (even if not quite to the level Skenes can be), and then trade him before he became truly expensive.

We know this is the end-game here. We know there is a very specific and set timeframe in which they have to win while Skenes is still wearing their uniform, and that clock is ticking. Loudly. It is the type of timeframe that should immediately increase the urgency of both ownership and the front office to do whatever they can to win, and win quickly.

Skenes is the type of player that does not come along very often, and when they do, and when you are lucky enough to get them, your only objective should be “how can we build the best possible team around this guy.”

The urgency is especially important when that player is a pitcher in the modern era, where at any point in time they could be lost for an entire season due to some combination of ligaments in their arm falling apart.

That is what leads us to the feeling of hopelessness.

Where is the urgency?

Where is the effort to put together the best possible team?

Not only because they have a player as good as Skenes, but also because they play in what might be the most watered-down division in baseball without a single contender among the group. The National League Central is an insanely winnable division, especially if the Pirates starting rotation actually meets its expectations, not only with Skenes, but also Jared Jones (assuming his elbow has not fallen off) and Mitch Keller, as well as the pending arrivals of Bubba Chandler and Thomas Harrington at some point this season. That pitching staff, if you just get in the playoffs, could potentially cause havoc on opponents in a short series.

This should have been an aggressive offseason, even if not in free agency, but in the trade market to try and find real, meaningful upgrades at pretty much any position on the field.

Instead, their biggest moves were….

• Trading Luis Ortiz for first baseman Spencer Horwitz. Horwitz posted solid numbers in Toronto a year ago, and he might be an upgrade over what they had at the position, but has heavy platoon splits and is going to miss an unknown amount of time with a “chronic” wrist issue that the Pirates apparently knew about when they acquired him. “Chronic” and “wrist” are two words you do not want to see in succession when talking about a hitter.

• Signing starting pitcher Andrew Heaney late in the offseason. He is a viable backend Major League starting pitcher, and brings some necessary depth. You can never have too many pitchers because somebody is going to get hurt, or not develop, or just not be what you hoped. He’s fine. Having a strong opinion in either direction beyond that is probably putting too much energy and analysis into it.

• Signing one-year stop-gaps like Tommy Pham and Adam Frazier that do not really add anything of significance. Pham certainly brings a little bit of crazy, and who knows, he might even punch somebody if things get really bad, but there is a reason this is his EIGHTH team in the past four years. He’s a bench player. A platoon player at best. He’s not solving an everyday hole, and only adds another frying pan-gloved outfielder to an already questionable defensive outfield. And he’s the best of the two players mentioned here. I have no idea what Adam Frazier brings.

• Taking some fliers on bullpen guys. I am not going to pretend to have any reasonable expectations for any of them — and neither should you — because there is not a more volatile group of players in the league than bullpen arms. They might be good. They might be bad. Nobody truly knows until they step onto the field and start throwing.

That is it.

That leaves them with a lineup that is still full of holes and question marks.

If you went position-by-position there are probably only two players — Bryan Reynolds and Oneil Cruz — that would start for a contending-caliber team.

Everybody else is either not good enough (Isiah Kiner-Falefa; the left fielders), or a huge question mark with an extensive list of variables that could go one way or another.

Maybe Ke’Bryan Hayes back will allow him to play 140 games and maybe he will hit with something that resembles power.

Maybe Joey Bart’s 2024 season was not a fluke and he just needed an opportunity.

Maybe Nick Gonzales will re-adjust to the adjustments the league made to him in the second half of the season (something not talked about enough was how bad he was after his first month).

Maybe Spencer Horwitz will get healthy and be decent.

Maybe Jack Suwinski be more like 2023 Jack Suwinski and less 2024 Jack Suwinski.

Maybe Endy Rodriguez comes back from his injury and shows he is still a legit prospect with a future in the league.

Maybe maybe maybe maybe maybe maybe maybe. MAYBE.

MAYBE.

Some of those variables might go their way. I am more optimistic about, say, Joey Bart or Nick Gonzales than I am Ke’Bryan Hayes or Jack Suwinski. But the more maybes and ifs you throw into a situation, the more likely it is some of them are going to fail.

The Pirates do not have the margin for error for some of them to fail.

The hopelessness is the confluence of three different rivers of depression and failure.

It is bad ownership meeting up with an incompetent staff of baseball operations people and both of them flowing into the river of baseball’s league-wide economic situation.

We know the Pirates are not going to spend like the Los Angeles Dodgers or New York Mets.

Maybe they can’t.

But could they do better and do more? Even a little bit more?

Even if they could, what is the level of confidence that Ben Cherington and his baseball operations people would spend it wisely? Because they have not done that when they have spent money. Nor have they proven that they can develop talent. At least position player talent.

Cherington is entering his sixth season as the Pirates general manager, and so far the best position players that have come through the system that he was responsible for acquiring — either by draft or trade — are Suwinski and Gonzales. While Cruz was mostly developed under his watch, he was initially acquired by Neal Huntington.

Even worse, other than Endy Rodriguez — who might be the best position prospect acquired by Cherington — the only player that is even remotely close to being a Major League player is Termarr Johnson and he has only played 14 games of Double-A ball. He is years away from being a factor. If he ever is. Same goes for Konnor Griffin.

How, in six years, does your farm system only produce a couple of replacement players with nobody else even close to contributing?

It is a big problem.

It is also a big problem that the Pirates have not signed a Major League free agent to a multi-year deal since 2016. That is almost a decade. There are only five other teams in Major League Baseball that have not signed a multi-year free agent within the past TWO offseasons.

That brings me back to this season feeling more hopeless than past bad teams or eras of Pirates baseball.

Even in some of the bad Dave Littlefield years, there were still things you could point to — even if in hindsight — and say, okay, at least there is something. Like the 2003 season when they signed legitimate Major League bats like Reggie Sanders, Matt Stairs and Kenny Lofton in free agency. That team also had two of the 65-highest paid players in baseball with both Brian Giles and Jason Kendall both making more than $8 million per season (a big number for that time).

I would crawl over five miles of broken glass to have a Matt Stairs signing this offseason.

Not even the 2003 version of Matt Stairs. I would settle for Matt Stairs as he is today. Whatever he is doing.

Not only do the Pirates not have a single player in the top-65 of salary this season, they do not have a single player in the top-100.

Mitch Keller is the highest at 106th.

Bryan Reynolds is second at 141st.

They are the only two within the top-210.

Isiah Kiner-Falefa (211th) and Ke’Bryan Hayes (220th) are next.

Hayes’ contract seems big to Pirates fans because it’s a level they rarely reach with players. But it is very much a mid-level baseball salary in 2025.

Even in the Neal Huntington era when players like McCutchen, Starling Marte, Neil Walker and Cole started to arrive, they accompanied them with free agents like Russell Martin and Francisco Liriano.

There is nothing even close to that level of effort or commitment now.

Honestly I feel like my expectations are low. I am not asking for or expecting Juan Soto or Max Fried or for them to out-bid the Dodgers for players like Yoshinobu Yamamoto. I am not asking for a top-five or even top-10 payroll.

I am just asking for some decent prospects. I am asking to trade for Nathaniel Lowe instead of Spencer Horwitz. I am just asking to make it look like you are even making a minimum effort to win before Paul Skenes is a Dodger. I am asking to not have to watch another season of Ji-Hwan Bae and Jack Suwinski.

This should not be a big ask. It apparently is.