In 2018, the Pittsburgh Pirates started to rebuild their team after several years of making the playoffs but not making it far.

They started it off by trading players like Andrew McCutchen to the Giants and Gerrit Cole to the Astros. And in 2019 they hired former Red Sox general manager Ben Cherrington to replace Neal Huntington as general manager.

But six years after the Pirates hired Cherrington, the Pirates are still in a rebuild, and it does not look like there is much improvement for the upcoming season.
Cherrington was successful as the GM of the Boston Red Sox from 2011 to 2015, as the team won the World Series in 2013 and had winning records for two of the years.
But Cherrington was not smart with money and made some questionable signings in his time in Boston. In 2014, the Red Sox made two of the worst signings in team history as they signed Pablo Sandoval to a five-year deal worth $95 million and prospect Rusney Castillo to a seven-year, $72.5 million contract. In 2015, he also signed Hanley Ramirez to a four-year deal worth $88 million, and even though Ramirez was decent, he was not worth the money.
When Cherrington came to Pittsburgh, he ended up being a completely different person: He was not spending any money and is still not. In 2022, the Pirates signed young third baseman Ke’Bryan Hayes to an eight-year deal worth $70 million and in April they signed Bryan Reynolds to an eight-year, $106.75 million contract. Those two are big signings, but they are the only big signings that have happened since Cherrington came to Pittsburgh.
Pirates owner Bob Nutting is part of the reason why the Pirates are not spending money, but the Pirates should not still be having losing seasons because of it.
Over the years, the Pirates have not made many powerful moves that impacted the team. They traded almost all of their players who would have been entering arbitration or free agency for prospects, and whenever the prospects get to the same stage, the Pirates trade them for new prospects.
So the Pirates get stuck with a ton of prospects and very few players who are MLB ready.
They also signed free agents over the years that have included Rich Hill, Carlos Santana, and Jose Quintana. They are solid players and can help get teams wins, but Cherrington and the Pirates traded them away at the trade deadline for prospects.
Many rumors have gone around this offseason that the Pirates would be getting star free agents like Jack Flaherty and Eduardo Rodriguez. But with pitchers and catchers reporting to spring training on Wednesday, the Pirates have not signed players who are not as good as Flaherty and Rodriguez. So far, this offseason, the Pirates have spent around $46.5 million. They are one of the 10 lowest-spending teams this offseason.
Based on the free agents the Pirates signed, this year is looking like another season that the Pirates have seen in previous years.