Mandatory Credit: D. Ross Cameron-USA TODAY Sports

The Pittsburgh Pirates were once among baseball’s gold standard of franchises.

They lost the first ever World Series. A parade of greats from Honus Wagner to Roberto Clemente donned the black, gold, and white and scooped up five World Series wins along the way, including over the favored Yankees in 1960.

These days, the Pirates aren’t even lovable losers. They’re basically a glorified farm team for MLB’s 29 other squads. The Yankees have done business with Pittsburgh often, most recently trading prospects for Jameson Taillon.

Otherwise, the Pirates don’t prioritize winning anymore. Former Red Sox general manager Ben Cherington runs their bare-minimum player development playbook. Prospects are developed and if they succeed enough over time, they’re usually traded for even more young talent to develop.

This vicious cycle is about to repeat itself courtesy of star outfielder and rumored Yankees target Bryan Reynolds. This could make for some fireworks if Brian Cashman makes the deal and the Yankees then visit PNC Park in September.

But if we’re being honest, that’s the best the Pirates can hope for this year. With or without Reynolds, they’re not good enough to beat the Mets either when they host them in June or visit Flushing in August.

It’s been a sad, long fall for the storied Pirates, whose three consecutive Wild Card bids from 2013-15 seem a lifetime ago. How many lifetimes will it be before they’re serious World Series contenders again?

Greatest Addition: Andrew McCutchen. The former MVP is back where it all began on a simple one-year $5 million deal. McCutchen spent the first nine years of his career with the Pirates and was an elite five-tool player, batting .291 with 203 home runs and five All-Star nods to go with his MVP trophy.

Now 36, McCutchen is wrapping up what could be a Hall of Fame career. What matters more is that he and Yankees ace Gerrit Cole were the faces of the Pirates’ last playoff run. He knows what it’s like to win in Pittsburgh when the odds are overwhelmingly stacked against you. His leadership will be invaluable to this latest Pirates youth class.

Greatest Loss: Diego Castillo, even if he isn’t much of a loss on paper. 2022 marked his MLB debut and he hit .206 with 11 home runs in 96 games, mostly as a utility player. It’s hard to blame the Pirates for trading him to Arizona for depth in December, what with his .251 on-base percentage (OBP) and 26.5% strikeout rate.

The issue more is the Pirates gave up on Castillo after such a small sample size. The former Yankees prospect was traded for Clay Holmes in 2021 in the midst of a career season in the minors, batting .278 with an .843 OPS and 19 home runs. He’s still only 25 years old too, so there’s every chance Pittsburgh could wind up regretting the trade.

Greatest Strength: Oneil Cruz. Imagine Aaron Judge but as a shortstop who bats left-handed. That’s Cruz, who played in 87 games last year and slugged 17 home runs despite a weak slash line. Cruz posted a .744 OPS, but hit just .233 with a .294 OBP.

So how does that make Cruz the Pirates’ greatest strength? Simple. Reynolds wants out and Pittsburgh will need a new face of the franchise. Cruz is only 24 and hit .310 in the minors in 2021.

If he can up the walks, down the strikeouts, and not be so all-or-nothing at the plate, Cruz’s star should rise fast in 2023.

Greatest Weakness: Bob Nutting. Major League Baseball is lucky that only a few of its teams’ owners are truly bad. Nutting, however, might be the worst. He assumed principal ownership in 2007 and has nothing to show for it. The Pirates’ recent Wild Card runs had nothing to do with him. It was all manager Clint Hurdle and former GM Neal Huntington’s work.

Bob Nutting isn’t an absentee owner, but an indifferent one. What’s worse is that it’s 100% intentional on his part. The Pittsburgh Post-Gazette reported last year that team payroll is tied entirely to ticket and concession sales. All TV revenues and monies received from MLB’s revenue sharing goes right to Nutting as a profit.

It’s clear why the Pirates were one of four teams named in a 2018 grievance filed by the MLBPA. Ownership has no interest in actually investing in the team and seems more than happy to just collect ad revenue from PNC Park.

Pirates fans deserve better and everyone knows it, perhaps even Bob Nutting himself.

Is there any saving the Pittsburgh Pirates? No, because change starts at the top. If the Pirates’ ownership cared about winning, the on-field performance would reflect that. The three recent Wild Card teams were because of well-timed prospects coming together with a select few free agents. Hoping that happens again year after year isn’t a sustainable model.

This is the Pittsburgh Pirates’ burden, curse, whatever you want to call it. Gone are the days of championship glory or even enjoying the first pro seasons of a young Barry Bonds. The Steel City is craving, starving, absolutely ravenously thirsting for championship baseball again despite attendance dwindling.

Until then, the Pirates shall just blindly wander through MLB like the ghost of an old Jolly Roger, quietly navigating the Three Rivers in search of days past.

Follow ESNY on Twitter @elitesportsny

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.