4 offseason decisions the Pirates already need to be thinking about for 2026

With the 2025 season winding down, the Pittsburgh Pirates don't have anything pesky on the horizon to worry about, like a future playoff matchup. While fans surely would trade some October activity for a jump on the offseason plans, the open calendar should give Ben Cherington plenty of time to formulate his offseason plan of attack while getting a jump on his rivals.

The Pirates have a lot of needs and an owner who keeps a vice-like grip on the checkbook. The work won't be easy. Cherington will have to find a way to make several key improvements to the team while also turning short-term assets into long-term ones without spending a lot. As a result, some key decisions await the polarizing executive.

The Pirates need to be thinking about these four key offseason decisions now

4. How much money to eat in a Mitch Keller trade (or how much of a lesser package to accept to clear his salary)

What looked to be a hot trade market for starting pitching ended up being pretty frigid at this year's deadline. With the lack of a true ace on the market, starter-needy contenders balked at the sky-high prices that sellers were asking for their coveted arms.

One of the better starters thought to be available was Pittsburgh's Mitch Keller, who had more than a handful of suitors rumored to be in pursuit of his services. Ultimately, the Pirates declined to move him, and one anonymous rival executive was quoted as saying his team had "not even bothered" to continue their negotiations due to Pittsburgh's reluctance to engage.

The likely sticking point was money, with Keller owed a hair over $55.7 million over the next three seasons. The decision to hold onto him and forgo whatever young offensive talent and salary relief a trade partner could have provided may prove to be a costly one.

Keller has done what he normally does and had a poor second-half showing that will not only confirm the skepticism about his ability to be more than a mid-rotation starter, but also give opposing clubs even more pause about taking on all or most of his contract.

Complicating matters further is that a team in need of rotation help could simply sign a free agent, rather than give up valuable young assets to acquire Keller and a contract that they didn't negotiate.

Pittsburgh doesn't have to deal Keller now. They can wait until next year's deadline and hope that his value improves. However, moving on from Keller allows them to cash in likely their best chip to find promising young offensive talent, but to do so, they'll have to decide how much money they're willing to eat or how much of a discount in terms of a prospect package they're willing to give in order to get his money off the books.

3. Find cost controlled young hitters with upside

The most important thing for the Pirates to do is add young, talented hitters to a lineup that is largely devoid of both. With a lineup that will likely finish last in the majors in runs scored, position is secondary to finding players who can actually hit and grow with Pittsburgh's young core.

At the same time, Pittsburgh has to be careful. Acquiring young big league talent likely means surrendering prospect capital, and for a team that is not exactly close to contention, trading away the future for some present gains would be shortsighted.

Some logical targets exist, though. Rumors have swirled that theBaltimore Orioles could shop catcher Adley Rutschman following the extension given to top prospect Samuel Basallo. The 2019 first overall pick is exactly the type of player the Pirates need to target, given his talent and remaining team control, but also the fact that injuries and inconsistencies have limited him recently, thus depressing his price tag a bit.

Taking a swing or two like this could be transformative for Pittsburgh, and having a few former top prospects to mentor the next generation of Pirates hitters as they go through the inevitable trials and tribulations could be invaluable.

2. Fill out the lineup and bullpen with low-cost, short-term veterans

Like a seasoned deal hunter, Pittsburgh needs to carefully comb through the bargain bin to uncover a handful of hidden gems — cheap veterans who can be had on one-year or short-term contracts. These veterans will serve two purposes. First, they'll allow the Pirates to fill out their lineup and bullpen with competent big league talent. Second, if they perform well, they could turn into valuable chips come the trade deadline.

There's a third potential benefit here. If the Pirates can find a couple of steals to fortify the lineup and the bullpen, the strength of their rotation (behind Paul Skenes, Bubba Chandler, the returning Jared Jones, and others) could propel them to surprising heights next season.

Seems far-fetched, but the rotation is legitimately good, and the Pirates have shown in 2025 that they can win ball games, especially at home. Now imagine what they could do if they had a competent offense.

1. Decide if Oneil Cruz is a part of their future and then act accordingly

When the Pirates announced that only Paul Skenes and Andrew McCutchen were untouchable at the trade deadline, more than a few eyebrows were raised by a surprising omission, the implication being that Oneil Cruz could actually be moved.

The Pirates have been waiting for Cruz to arrive for a while now. The 27-year-old has shown flashes, but something has always gotten in the way of him putting all of his tools together.

Since that deadline proclamation, Cruz has hit just .157/.254/.259, bringing his season line down to .203/.303/.379 with 19 homers and an 87 wRC+. While he's always struck out a ton, his 2025 numbers are the worst of his career, and he's getting too old to carry the "promising young player" label.

Pittsburgh doesn't necessarily need to trade Cruz right now. In fact, with team control through the end of the 2028 season and a career-worst offensive performance, it would be foolish to move him when his value is at its lowest.

That doesn't mean, though, that the organization shouldn't be looking long and hard at how they see Cruz's place in their vision for the team's future and begin taking the necessary steps to find a replacement - or lock him up if they believe in a turnaround. This isn't an urgent task, but it is an important one.