Can Pirates retain their best players long term?

Can’t buy me love, but the Pirates could at least try to buy a first baseman.

The season is coming to a close and the Pittsburgh Pirates are already looking ahead to next year as another campaign has come and gone without a playoff berth and another losing record under Derek Shelton. Moving forward, there needs to be some kind of a plan to dump those that are not meeting the standard and retain those that are making a difference. However with the current climate surrounding the team and the various issues with culture, can the team hold onto their few stars if they wanted to?

I wish I could pinpoint the specific problem with the team, but at times it feels like anything and everything is the issue. Notably, the team has done a poor job at developing its hitters. Oneil Cruz should be the best hitter on the planet, and yet he’s still not as capable as 37-year old Andrew McCutchen. Even free-agents who are known to have good offensive output struggle when they sign or are traded to the team. Bryan De La Cruz had 19 homers this season before being traded to Pittsburgh, with only 5 since then.

Moving forward, with the issues afoot at this time, the team has to decide who they need to hold onto, especially if they go into full rebuild mode again.

Bryan Reynolds for whatever reason is always the subject of trade conversations, and given that he had contract issues with the team previously, he could be a huge domino to fall. In April of 2023, Reynolds and the Pirates reached an agreement on an eight-year contract worth $106.75 million. Despite becoming the highest paid Pirate of all-time, he has still been connected to trade talks. The team has not done well, and with every slump and setback it feels like they could be closer to losing Reynolds. The length and dollar value of his contract could help to prevent this, but the team needs to take major steps to avoid that altogether.

I believe Ke’Bryan Hayes and Oneil Cruz have star potential and given the right situation could thrive. I’m not sure if they both stay in Pittsburgh long-term, especially given their shortcomings, but there is such a high ceiling for the both of them. April of 2022 saw Hayes sign his own massive contract extension for eight years, but the team has seen minimal returns on their $70 million dollar investment. Cruz has yet to sign any kind of long-term deal with Pittsburgh, and I’m honestly not sure it’ll come given his track record.

As for Jared Jones and Paul Skenes, they’re the two with the most upside right now and may be two of the most essential members of the team. It has been too long since Pittsburgh has had a quality rotation, and losing either one of these pitchers would once again set the organization back years. Rookies in Major League Baseball are under team control during their first six years of service, so outside of them requesting trades, they should be around for the time being as long as the organization doesn’t completely implode on itself.

In the case of Skenes and Jones, they are box office players. Skenes especially has superstar potential, and with a championship pedigree it’s not unlikely that he will grow tired of the team’s struggles. I’ve already seen plenty of memes and posts online saying Skenes is gonna make a great Dodger one day, I’ll be sick to my stomach if that happens.

The Pirates are a notoriously cheap franchise and have shown that they are not willing to spend the money necessary to build a winning team. The coaching staff is also not capable of improving upon the team that they have, and has the club stuck in this inhospitable wasteland at the bottom of the NL Central. If they are at all concerned about the fate of their few quality players and impending free-agency, they’ll be sure to right the ship before it’s too late.