The Pittsburgh Pirates have a rare opportunity in front of them, built around elite young pitching, but their latest free agent signing shows how cautiously they are still approaching a moment that demands urgency.
Everything starts with Paul Skenes. In back-to-back seasons, he has already established himself as one of the most dominant pitchers in the sport, following a Rookie of the Year award in 2024 with a National League Cy Young in 2025.
He has delivered nearly eleven wins above replacement before his twenty fourth birthday. Arms like that do not come around often, and when they do, front offices usually respond aggressively.
The rest of the rotation suggests this is not a one player fluke. Bubba Chandler remains among baseball’s most highly regarded pitching prospects.
Jared Jones looked the part early in 2025 before an elbow injury halted his progress, with a return expected next season. Mitch Keller provides innings and experience. For once, Pittsburgh‘s rotation looks like something that could anchor a postseason run.
For years, the Pirates have lagged behind the league offensively, and this offseason was another chance to address it in a meaningful way. High end bats were available. The market included players capable of changing how opponents pitch and defend. Pittsburgh again stayed on the margins.
That hesitation is rooted in history. Before this winter, the Pirates had not signed a free agent to a multiyear deal since 2016, when Ivan Nova received a three-year contract.
That signing did not work out, and in the years since, owner Bob Nutting has avoided committing long term money to outside players. Extensions for homegrown talent became the limit of ambition.
A step forward that still feels small
The Pirates agreed to a two year, 29-million-dollar contract with Ryan O’Hearn, officially breaking a decade long pattern. By Pittsburgh standards, it counts as progress.
O’Hearn is a solid addition, not a centerpiece. He does not reshape the offense or force opposing teams to adjust their approach.
Even with the addition of Brandon Lowe earlier in the offseason, Pittsburgh remains thin beyond a handful of reliable hitters. Compared to teams that spend aggressively to support elite pitching, the gap is obvious.
Meanwhile, Skenes will not spend his prime years in Pittsburgh. When free agency arrives, he will command a contract that reflects his historic start, and the Pirates are unlikely to be part of that bidding. That makes the present window critical. Waiting for internal development alone is a risky strategy when the foundation is already in place.
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