PirateFest finally kicked off on Saturday, Jan 24. Fans have been eagerly waiting for this day. Do you know why? Well, the Spring training is less than a month away, and the Pittsburgh Pirates legend, Andrew McCutchen, is without a contract. Many voices across the MLB are still optimistic about the 39-year-old’s return to the league. However, GM Ben Cherington served reality on a platter.

At PiratesFest’s Ask Management session, a preselected question put Ben Cherington on the spot about the current status of McCutchen. Andrew has meant a ton to the team. He’s had an incredible run in two different times with the Pirates. Certainly, his legacy as a Pirate is secure, and our desire — everybody at the Pirates would desire — to have him maintain a really good relationship with Andrew well into the future,” Cherington said.

He added, “And then we come back to our team. What is the job? The job is to build a team that gives us the best chance to be winning games when you’re in the ballpark in June and July, and that’s where I see that passion come out. That’s ultimately what our job is and what we aim to do. And so our approach this offseason has been laser-focused on what gives us the best chance to win more baseball games in Pittsburgh than we have in the past seasons. That’s going to continue to guide our decisions.”

Andrew McCutchen currently remains without a deal. As of January 2026, the 39-year-old stands on the open market after completing a one-year $5 million contract with the Pittsburgh Pirates in 2025. Talks slowed in mid December 2025. By January 20, 2026, no resolution followed.

However, the situation cuts deeper than paperwork. McCutchen long symbolized continuity in Pittsburgh, bridging eras and steadying a young clubhouse. Therefore, roster construction now drives the conversation. The Pirates added Ryan O’Hearn (2 yrs, $29M) and Brandon Lowe to raise competitiveness. Consequently everyday designated hitter duties grow harder to justify. Defensive usage also remains limited due to age management.

Now, the Pirates have an advantage with the CBA reservations, but the question is, will Bob Nutting utilize that to hand Andrew McCutchen a new contract?

Bob Nutting might have the key to Andrew McCutchen’s comeback

The MLB’s Collective Bargaining Agreement sets the CBT for teams exceeding payroll limits, with proceeds redistributed league-wide. Pittsburgh benefits heavily yet continues operating far below the $241 million threshold. In 2024, payroll sat near $123 million. Projections for 2026 range between $100 and $120 million. As a result, the Pirates remain among MLB’s most profitable franchises.

Therefore, the 2026 offseason reflected selective spending rather than aggression. Pittsburgh signed Ryan O’Hearn for two years at $29 million. The club also landed Brandon Lowe, Mason Montgomery, and Jake Mangum through a three-team swap. Additionally, Jhostynxon Garcia and Jesus Travieso arrived from Boston for Johan Oviedo. These moves added power and experience without shifting payroll philosophy.

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Meanwhile, Andrew McCutchen’s future stays unresolved. The Pirates project a $96 to $102 million payroll for 2026, including Mitch Keller at $16.5 million and Oneil Cruz’s arbitration near $11 million. That leaves nearly $140 million before tax penalties. Ownership reportedly held $30 to $40 million in flexibility. Consequently, a $5 million reunion with McCutchen remains financially effortless under the CBA.

This offseason feels like a pause before a verdict. PiratesFest revived hope, yet caution still rules the room. Andrew McCutchen remains the emotional center, even without ink. Meanwhile structure steers every move. Therefore, the question lingers louder than cheers. Will legacy meet logic, or will Pittsburgh finally turn the page with intent?