PITTSBURGH -- The Pittsburgh Pirates once again face a critical offseason. Unlike in previous years, however, the Buccos enter the coming months with expectations backed by real results. After the team won 82 games in 2026, the floor has been raised for their 2027 campaign.

In many ways, this doesn't feel that different from offseasons past for the Pirates. They have a high-ticket free agent destined to depart in a few months while they sort out multiple players who are arbitration-eligible.

But if the Pirates play this right, this could be the most important offseason in a long time in Pittsburgh.

Decisions to Make on Franchise Pillars

Two of the Pirates’ most important players face arbitration in the next few months. Pirates ace and 2025 Cy Young winner Paul Skenes will go through the process for the first time, and it’s possible he sets an MLB record for first-year arbitration-eligible players. That could net him a salary north of $7.25 million, which would eclipse the previous high for a pitcher set by Dallas Kuechel.

Even after a down 2026 campaign, that salary is an underpayment for Skenes. He’s the face of the franchise, one of the premier players in the MLB, and the team’s best player in decades. The Pirates just have to get through this arbitration process without upsetting the All-Star pitcher.

Meanwhile, slugger Oneil Cruz is set for an arbitration battle of his own. Cruz missed two months of the 2026 season, but still blasted 20 home runs and stole 30 bases. He’s projected to make over $6 million if this reaches the hearing, but the Pirates might be smart to work toward a long-term deal with the left-handed slugger.

Navigating the Looming Lockout

What stands above everything else this offseason is the possibility, or perhaps likelihood, of the MLB not playing the 2027 season. The league’s Collective Bargaining Agreement ends December 1, 2026, and with less than two months until that date, there is little optimism about a new agreement being finalized.

That will have a huge impact on the Pirates, especially with their long list of arbitration eligible players.

But it also will have a noticeable impact on long-term deals. With no assurance that the coming league year is played, the organization is going to be even more hesitant than usual to dish out huge money over multiple years.

It might work out to their advantage, however. The looming deadline might push some players to finalize deals before the work stoppage. Maybe that benefits the Pirates and their negotiations, allowing them to sign one of their top arbitration-eligible players to a team-friendly long-term deal.

The Pirates face an intriguing and possibly terrifying offseason. With so much uncertainty around the league, no one knows exactly how to proceed. The Buccos are stuck in the middle as they figure things out, but they could turn this into the most important offseason in recent memory.