Pittsburgh Pirates: Vital Offseason For Ben Cherington Off to a Slow Start

It is a vital offseason for Ben Cherington and the Pittsburgh Pirates, and it's an offseason that's off to a slow start. They will have an opportunity to change that starting this weekend.

There is no way around it, this is a vital offseason for Ben Cherington. He is preparing to enter his 5th season as general manager of the Pittsburgh Pirates, and, based on team winning percentage, the first four have produced one of the worst four-year stretches in modern franchise history.

Considering it's the Pittsburgh Pirates were talking about, putting together a foru-year stretch that is that poor is not easy to do. Yet, here we are. Due to this, Cheginton's job could very possibly be on the line entering 2024.

It's not like there is a lack of needs for the Pirates this offseason, either. As of now, the team needs at least three quality, reliable starting pitcher. They have no first baseman, second base is a big question mark, the bullpen could use another late inning arm or two, and what happens with the third outfield spot/designate hitter is up in the air as well.

Not only does this need to be a busy offseason for Cherington because the team desperately needs to take a step forward and attempt to compete in 2024, but also because the team's roster has a long way to go in order to get to that point. So, a slow start to the offseason is going to bring frustration among fans. That's human nature. It is made even worse by the track record of this front office of having less than busy offseason.

Adding to the frustration thus far for Pirate fans has been the actions of the rest of the NL Central division.

The Reds have already made a pair of additions to their pitching staff in the form of Emilio Pagan and Nick Martinez, two pitchers who could have helped the Bucs and were signed to deals the Pirates easily could have afforded. No team in baseball has been more aggressive in attacking the starting pitching market than the St. Louis Cardinals.

While the Chicago Cubs have not made any significant moves yet, they have been tied to multiple noteworthy free agents. The expectation is for the Cubs, who already have a much better roster than the Pirates, to be active. Even the potentially rebuilding Milwaukee Brewers made a splash by inking top prosepct Jackson Chourio to an 8-year, $80 million deal before he has even played in the majors.

Meanwhile, the Prates, who as of this writing, have the worst roster in the division by a large margin have yet to make a move. As Nick wrote about earlier this week, there have not even been any worthwhile rumors surrounding the Pirates. This also adds to the frustration of the fan base.

As was mentioned above, things could begin to change for the Pirates this weekend. Well, the opportunity will be there for that to happen at least. MLB's Winter Meetings will begin on Sunday and run through Wednesday.

At the Winter Meetings, general managers and front office executive from across baseball will be able to meet in person. This can make swinging trades much easier to accomplish, and as Jason Mackey of the Pittsburgh Post-Gazette has hinted at, the Pirates may look to go this route more so than free agency to address needs.

To circle back to free agency, team's can also meet with player agents in person at the Winter Meetings. This can make coming to terms on free agent deals much easier for all parties involved as well.

If the Pirates come out of the Winter Meetings with no or few moves made, then fans will really be readying the pitch forks. And, truth be told, rightfully so. Cherington's future may ride on this offseason, and it's time for him to start to become aggressive when it comes to improving the worst roster in the NL Central.