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.